Home Vacation Home Rentals By Owner In Chatham, MA

Showing 280 Of 362 Vacation Rentals
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Exceptional(15)

$596.7

/ Nightly
Private Vacation Home

Sea views steps to Ridgevale Beach - Airy Cottage. Modern Amenities. Pet.linen

Chatham, Massachusetts, United States

Pet ok with approval first. Bright and airy cottage sleeps max 5 (2 BR - 1Q, 2T) plus single pull out sofa bed in hi living room. A block by footpath from Ridgevale Beach. Linens included. No pets permitted. Classic beach cottage with original pine interior, now bright and freshly painted with updated modern conveniences (including a/c, WiFi, washer, dryer, dishwasher, smart TVs with cable). Water views and beautiful sunsets from large second-story sun deck (accessed via exterior stairs at back of house) with seating/dining table. Living room plus separate family room with dining area. Well-equipped kitchen. Bathroom has shower (no tub) plus a fully-enclosed outdoor shower at back of house to enjoy with hot/cold water. brbrThis traditional but updated Cape Cod beach cottage is steps to the warm, safe waters of Nantucket Sound on the south side of the beautiful, unspoiled town of Chatham on the elbow of Cape Cod. Ridgevale Beach is Chatham's most popular warm-water family beach. It's a long, wide sandy beach with tidal inlets perfect for exploring. Safe, gradual sloping sandy bottom ocean swimming with small waves. brbrLots of activities at your doorstep: fish, swim, build sand castles, windsurf, sail, canoe. You can get food, equipment and boat rentals at the Ridgevale Beach Snack Bar - just two minutes walk from the cottage. And just a five-minute drive to all that downtown Chatham has to offer.brbrPast guest book comments have been ' perfect romantic getaway ' , ' Beach access is big plus' 'gorgeous views' ' would recommend to anyone' 'We had a great time- the kids met so many friends on the beach. brbrParking for max two cars in driveway - no parking allowed on lawn or in street. brbrThe cottage is in a safe, upscale beachfront neighborhood on a dead-end street. Access to beach footpath is diagonally across street from cottage.
Bed 2

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Bath 1

Bath

Sleep 5

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Exceptional(16)

$786.64

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Private Vacation Home

Waterfront on Private Lake!

Chatham, Massachusetts, United States

Summary:brbr16644 - Lover's Lookout: Waterfront on Private Lake!brbrbrbrThe Space:brbrEnjoy your best days of summer at our waterfront home located on the private Lover’s Lake in central Chatham! Bring or rent kayaks/SUP boards (Chatham Kayak Company is close by!) and cast away on the water soaking up the Cape Cod sun! Craving a little salt Not to worry, Jackknife Beach and Harding’s Beach are both just a 5-10 minute drive away. brbrWhen you are all watered out, come back to the house to grill dinner on the gas grill and enjoy a meal on either the 2nd-floor deck or covered patio. Head back towards the water and relax in an Adirondack chair and watch the sunset paint the sky over the lake! Alternatively, brighten up a rainy night by making a homemade meal in the newly renovated kitchen, bright and clean with glistening white subway tiles and Stainless Steel Samsung Appliances. Enjoy an appetizer in the living area then share a meal around the formal dining table and admire the gleam of the steel art and decorative fireplace in the light. After dinner, retreat downstairs to the TV/Game Room for some late-night fun. Play a game of foosball, eat some popcorn and watch a movie on the couch, or indulge in a classic board game like Trivial Pursuit or Scrabble.brbrWhen you’re finally tuckered out from the day, head your separate ways to one of our home’s 4 bedrooms that sleeps up to 9 people. The main bedroom sits on the backside of the house on the first floor and features a King size bed-- where you can overlook the lake from a wall of windows that wraps around the back corner of the room. It also boasts a King bed, private Full Bathroom, TV, and a closet and dresser for ample storage. The second bedroom awaits across the home and struts a Queen Bed, TV, Full Bathroom, and large closet. The final two bedrooms are off of the Game Room on the ground floor. The third bedroom has one Queen and one Twin bed, closet and dresser, and its own door to the shared full bathroom-- which makes bedtime a breeze with two sinks! The fourth bedroom is across the floor and has two twin beds, a dresser, and a slider that goes out to the Patio. Central A/C on the 1st floor and mini-splits on the ground floor will keep you cool on the most feverish days of summer! Other top amenities include WiFi, cable TV, gas grill, and sheets and bath towels provided for each guest.brbrIf you’re up for exploring the town, stroll down Main Street Chatham, or catch the Chatham Angler’s (of the Cape Cod Baseball League) play at Veteran’s Field. While you're out and about, be sure to check out some of our favorite eateries too like Hangar B (serving the best brunch around!), Mom & Pop’s (grilling the best veggie burger you’ll ever have), or Mac’s Chatham Fish & Lobster (broiling/frying all the best of Cape Cod seafood). Our waterfront home is bound to leave you with everlasting memories of summer and steal your heart forever!brbrHome Details:br-Sleeps 9br-2 Floors (Ground Floor and 1st Floor)brBedroomsbr-Total 4br-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroombr-1st Floor Bedroom #2: 1 Queen Bed w/ en suite Full Bathroombr-Ground Floor Bedroom #3: 1 Queen Bed and 1 Twin Bed w/ en suite Full Bathroombr-Ground Floor Bedroom #4: 2 Twin BedsbrBathroomsbr-Total 3br- 1st Floor: Full Bathroom w/ Shower (en suite King Bedroom)br-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)br-Ground Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Central A/C on 1st Floorbr-Mini-Split A/C System on Ground Floorbr-Cable TV br-WiFibr-Fireplace NOT for guest usebr-Game Room (Foosball Table)br-Board Games/Gamesbr-Washer/Dryer br-Gas Grillbr-Deck with Furniturebr-Patio with Furniturebr-Private Backyardbr-Waterfront on Private Lakebr-NO pets (fines remitted)br-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0408780550brbrbrbrThe Neighborhood:brbrGeneral
Bed 4

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Bath 3

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Sleep 9

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$366.71

/ Nightly
Private Vacation Home

Central AC, Game Room, Dog-Friendly!

Chatham, Massachusetts, United States

Summary:brbr16701 - Chatham Bliss: Central AC, Game Room, Dog-Friendly!brbrbrbrThe Space:brbrWelcome to Chatham Bliss, where your Cape Cod dreams come to life. This inviting 3-bedroom, dog-friendly retreat comfortably hosts up to 6 guests and offers the perfect blend of charm, comfort, and coastal living in beautiful Chatham.brbrbrbrSettle into the bright, welcoming living room, where sliding doors open onto the deck and fill the space with natural light. The fully equipped kitchen makes it easy to gather and prepare meals with family and friends. When it’s time to unwind, you’ll rest comfortably in two plush queen bedrooms—one featuring a full bathroom with a shower—while the kids’ room, equipped with a twin bed and trundle, offers flexible sleeping arrangements.brbrbrbrOn the ground floor, a game room awaits, perfect for friendly competition around the pool table or cozy movie nights with your party. No matter the weather, it’s an ideal space to have fun.brbrbrbrA washer and dryer provide added convenience, making it easy to refresh after a day at the beach. A half bathroom on the ground floor and a full bathroom on the first floor, combined with WiFi, streaming TV, and central air conditioning, ensure comfort and ease throughout your stay.brbrbrbrStep outside and enjoy classic Cape Cod living. Fire up the BBQ grill for an easy family meal, then dine al fresco in the outdoor seating area. As the evening winds down, gather around the wood-burning firepit for cozy nights under the stars, sipping a glass of your favorite cocktail.brbrbrbrSpend your days exploring some of Chatham’s best beaches—Hardings Beach, Ridgevale Beach, and Cockle Cove are all less than a 10-minute drive away. For nature lovers, the Monomoy National Wildlife Refuge offers beautiful trails and coastal scenery. Just a short drive away, Chatham’s charming Main Street invites you to browse boutiques, art galleries, and local shops. Enjoy brunch at Pain D’Avignon, fresh seafood at The Impudent Oyster, casual bites at Mom & Pops Burgers, or sushi at Bluefins. Don’t miss the iconic Chatham Squire for a lively night out, and be sure to stop by the Chatham Pier Fish Market for the freshest local catch and a true Cape Cod experience.brbrbrbrWhether you're here for sun-soaked beach days, unforgettable dining, or pure relaxation, Chatham Bliss is your ideal home base. Book your stay and experience the very best of Cape Cod living.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 6brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 Queen Bed (Ensuite)brbr-1st Floor Bedroom: 1 Queen Bedbrbr-1st Floor Bedroom: 1 Twin Bed w/ TrundlebrbrBathroomsbrbr-Total 2.5brbr-Ground Floor: Half Bathroombrbr-1st Floor: Full Bathroom, with Tub/Shower Combobrbr-1st Floor: Full Bathroom, with Shower (Ensuite w/ Queen Bedroom)brbrOther Amenities brbr-Central A/C brbr-WiFibrbr-Smart TV brbr-Streaming Service brbr-Game Roombrbr-Pool Tablebrbr-Washer/Dryerbrbr-Propane Grillbrbr-Wood Firepitbrbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 2 cars maximumbrbr-C0569530550
Bed 3

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Bath 2

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Sleep 6

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Exceptional(22)

$868.68

/ Nightly
Private Vacation Home

5 Bedroom Chatham Charmer RPAM012

Chatham, Massachusetts, United States

Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation needs. Sleeping twelve people comfortably, you will have plenty of room to enjoy your stay in the large living room while the kids hang out in the adjoining family room. Featuring a first floor king master bedroom plus 2 queen bedrooms, 1 king bedroom, and bunk room with 4 single beds upstairs, there are plenty of options for sleeping arrangements. Charmingly appointed, everything you need to enjoy your time here is accounted for: an outdoor shower to rinse off after a day at the beach, gas grill on the spacious deck, plenty of parking, great location and a quick walk down the neighborhood path to Emery Pond for kayaking and swimming! Plus, air hockey and ping pong in the basement for those rainy days and corn hole boards for the sunny ones! Located just 1.4 miles to Main Street (a 15-minute ride on the bike path), you and your guests will have an easy time experiencing the outstanding dining and shopping that Chatham has to offer, or bring your tennis rackets and play a match at one of the several public courts. Be sure to stop by the famous Chatham Squire Restaurant and have some of the best fried seafood on Cape Cod, or head over to the world-renowned Chatham Bars Inn and enjoy a drink at their beach bar. You have easy drives to some of the best beaches around like Lighthouse Beach, Hardings Beach, or Ridgevale Beach. This home is also perfectly suited for weekend retreats in the spring or fall. Getting married Spend time with your wedding party in this expansive home and enjoy getting ready under one roof together! Central AC throughout the home will keep you cool on those balmy summer days. brTenants provide their own linens and towels. No pets please. Seven night minimum in the peak season, Sat. to Sat. Four night minimum the rest of the year. Subject to applicable taxes and fees. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.
Bed 5

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Bath 3

Bath

Sleep 12

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Exceptional(10)

$3826.83

/ Nightly
Private Vacation Home

Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026

Chatham, Massachusetts, United States

Located just .9 miles from the Chatham Bars Inn and 1.3 Miles from Main Street, this 6 bedroom 6 full bath luxury home sleeps 14 comfortably. Featuring a heated salt water pool and spa, this home is the definition of a Chatham luxury property with 5400 sq ft of living space. Across the street is the home's path to the beach with its ever changing views of Aunt Lydias Cove, Chatham Harbor and Tern Island.brbrAs you enter the home you walk up a set of stairs to a covered porch. Inside, the home is split into two separate wings connected by a breezeway. The main wing features a gourmet kitchen with an oversized island, multiple sitting/living areas, dining room with a table that sits 14, access to the decks with outdoor dining table and natural gas grill and a lovely screened in porch. Also in this wing are three ensuite bedrooms. The first floor bedroom has a king bed; upstairs you will find a queen bedroom and a bedroom w/ 2 single beds.brbrThe second wing of the home has a truly grand TV room, with a cloud couch for tons of seating. In this wing are the other three bedrooms. The first floor bedroom is a bunk room with 3 sets of twin bunks beds. There is a full bathroom off of the TV room for people sleeping here to use. Upstairs in this wing are two more ensuite bedrooms: one w/ a queen bed and one w/ a king bed.brbrThe back deck has a staircase that leads down to the pool area which is enclosed in decking and features plenty of seating and lounging options. The pool is heated, salt water based and gets plenty of sunlight. The spa is next to the pool, with controls for heating, jets and lights! The pool and the spa are professional maintained and cleaned weekly for tenants.brbrFrom the moment you step in the home, you will notice the amount of care and craftsmanship that went into the construction and renovation of this property. Bespoke details and thoughtful touches are around every corner. If you are looking for a premier rental in Chatham to make your stay to Cape Cod unforgettable, look no further...brbrThe home is available for year round bookings. Please see below for minimum stay requirements based on the time of year. Please note, off season bookings do not include the pool or spa.brbrSubject to applicable taxes and fees. No pets please. All linens and towels are provided. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.brbrSTAY REQUIREMENTS:br8/30/25- 10/3/25- 4 night minimum stays (Pool and Spa are Open)br10/4/25 - 5/15/26 - 3 night minimum stays (Pool and Spa are Closed)br5/16/26 - 6/26/26 - 4 night minimum stays (Pool and Spa are Open) br6/27/26 - 9/4/26 - 7 night minimum stays, Sat. to Sat. only (Pool and Spa are Open) br9/5/26 - 10/2/26- 4 night minimum stays (Pool and Spa are Open) br10/3/26 - 12/31/26 - 3 night minimum stays (Pool and Spa are Closed)brbrBEDROOM CONFIGURATION:brFirst Floor-brBedroom 1- 1 king bed w/ ensuite bathroombrBedroom 2- 6 twins beds in 3 bunk bed formation (bathroom in hallway)brSecond Floor Wing 1-brBedroom 3- 1 queen bed w/ ensuite bathroombrBedroom 4- 2 twin beds w/ ensuite bathroom brSecond Floor Wing 2-brBedroom 5- 1 queen bed w/ ensuite bathroombrBedroom 6- 1 king bed w/ ensuite bathroom
Bed 6

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Bath 6

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Sleep 14

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Exceptional(8)

$1151.95

/ Nightly
Private Vacation Home

Private Beach Front Chatham Rental Close To Everything RPAM054

Chatham, Massachusetts, United States

Nestled in one of the most coveted areas of Cape Cod, 63 Morris Island Road offers everything a discerning tenant could hope for. Location: .8 miles from the heart of Main Street, Chatham with world class shopping and dining options. 1.2 miles from Chatham Bars Inn for easy access to their restaurants and amenities. 800 feet from Chatham Lighthouse Beach… but why bother going there when you have your own private path to the beach just out your door…. This property encompasses multiple acres of land that stretch from the home all the way to the ocean. Spend your days walking down the path (about a six minute walk to the water) and exploring the coastline. Walk along the beach and come up the stairs at the Lighthouse and head into town for lunch.brbrThe main floor of the home has an open-flow that starts to the left of the front door with an oversized living room with vaulted ceilings, plenty of seating, TV and a large AC unit. To the right of the door is the dining area with a table that can easily seat everyone and a kitchen with counter seating and everything you need to prepare great meals. Another living area with couches and a TV is past the dining area and off of that you will find a private sun room with a small game table and cozy seating area as well as the first bedroom with a queen bed and AC unit. A separate laundry room and full bathroom with stall shower complete the floor. brbrThe second floor of the home features three bedrooms off a central hallway: one w/ a queen bed, one w/ twin bunk beds and a solo twin and a primary bedroom w/ a king bed, TV and a balcony with peaks of the ocean. Each bedroom has an AC unit. A half bathroom, plus a separate full bathroom with a tub/shower complete the second floor. The lower level of the home has a ping-pong table for spirited tournaments to keep things interesting! brbrOutside there is an oversized driveway for parking at least 6 cars, a large side yard with plenty of room for games, a back deck with a gas grill and additional seating/dining space and an outdoor shower to rinse off after the beach (or use for every shower while you are there!). brbrFreshly laundered linens will be dropped off the day of your arrival by a linen rental company at the owner's expense. Linens include bed linens, pillowcases, bath towels, hand towels and face clothes. Mattress pads, blankets and pillows will be at the house. Beach towels are not provided so please remember to bring your own if desired. All new stainless steel appliances have been added to the kitchen for the upcoming season. Subject to applicable taxes and fees. No pets please. Seven night minimums, Saturday to Saturday during the peak season. Seven night minimums, check in/out any day in shoulder/off seasons. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver insurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional damage protection which may be required at this property.
Bed 4

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Bath 2

Bath

Sleep 9

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Exceptional(8)

$495.96

/ Nightly
Private Vacation Home

SHORT WALK TO LIGHTHOUSE BEACH, ANDREW HARDINGS LANE BEACH AND TOWN!!

Chatham, Massachusetts, United States

Close to Town, Lighthouse Beach and Andrew Hardings Lane -- Desirable Old Village Location! brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis prime summer rental is immaculate and adorable. Just 2/10's of a mile to a classic Lighthouse Beach and just a short distance to town. You're sure to love the great front porch with rockers and spectacular cottage gardens, lovely patio and enclosed side yard. brbrIn early 2022, the owner completed a major refresh and update that included repainting the entire interior of the house, installed split air conditioning throughout the house, replaced all beds and mattresses, installed wall mounted flat screen televisions in the living room and primary bedroom, added indoor shutters in the living room, primary bedroom and upstairs second bedroom, added outdoor weber gas grill, replaced refrigerator, installed disposal, replaced kitchen sink and installed a Colligan water filtration system in the kitchen sink. There is a large outdoor dining table on the rear patio and immaculate outdoor shower. The house is equipped with WiFi and also has expanded cable service. brbrProperty is very sunny and bright, charming and comfortable, well maintained with all of the comforts of home. brbrOn the back side of the house there is a bedroom with two twin beds side by side. In the hallway next to this bedroom there is a bath with tub and shower. Upstairs there are two bedrooms and a bath with shower. The first bedroom has a queen size bed and television. The second bedroom has two twin beds side by side.brbrFirst Floor:brBedroom #1 - Two TwinsbrbrSecond Floor: brBedroom #2 - QueenbrBedroom #3 - Two Twinsbrbrbr* Additional fees:br- $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services feebr- $280 cleaning feebr- all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETS ALLOWEDbr* OCCUPANCY: 6 (Adults and children)br* PARKING FOR 2 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED. WE CAN PROVIDE INFORMATION FOR A LINEN RENTAL SERVICE.brbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC - CKAPP
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(5)

$485.63

/ Nightly
Private Vacation Home

Walk to Main St and Oyster Pond in Chatham!

Chatham, Massachusetts, United States

Summary:brbr16685 - Slack Tide : Walk to Main St and Oyster Pond in Chatham!brbrbrbrThe Space:brbrDiscover the epitome of Cape Cod charm at this vacation destination, nestled in the heart of downtown Chatham with subtle vistas of picturesque Oyster Pond. Positioned at the end of a tranquil road, this hidden gem offers both seclusion and convenience, with Downtown Main Street just a short, leisurely stroll away. As you step inside, you'll be enveloped by the welcoming ambiance of the open living room, flooded with natural light and boasting ample space for the whole family to gather and create cherished memories.brbrbrbrIndulge in the quintessential Cape Cod experience by spending your days basking in the sunshine at Oyster Pond or immersing yourself in the vibrant energy of Main Street Chatham. Explore an array of local shops, candy stores, and charming cafes, each offering a delightful taste of coastal living.brbrbrbrSavor al fresco dining experiences on the back patio, where balmy breezes and serene surroundings set the stage for unforgettable meals with loved ones. As the day transitions into the evening, retreat to the second-floor bedroom and witness the breathtaking spectacle of the sunset casting its golden hues over the tranquil waters of Oyster Pond.brbrbrbrWith Downtown Main Street Chatham just 0.4 miles away, adventure awaits at every turn. Explore the eclectic array of stores, from the whimsical delights of Chatham Candy Manor to the lively ambiance and live music at The Squire, where evening cocktails are accompanied by the sounds of laughter and melody.brbrbrbrEmbrace the essence of Cape Cod living at Slack Tide, where every moment promises serenity, adventure, and cherished memories to last a lifetime.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 8brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 King Bedbrbr-2nd Floor Bedroom: 1 King Bedbrbr-2nd Floor Bedroom: 2 Queen Bunk Beds (4 Queen Beds total)brbrBathroomsbrbr-Total 2.5brbr-1st Floor: ½ Bathbrbr-1st Floor: Showerbrbr-2nd Floor: Tub/Shower CombobrbrOther Amenities brbr-Mini Split AC’sbrbr-WiFibrbr-TVbrbr-Washer/Dryer brbr-Propane Grillbrbr-Indoor Fireplaces are not for guest use (fines remitted) brbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 2 cars maximumbrbr-C1382031003
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(5)

$631.82

/ Nightly
Private Vacation Home

Chatham Lakefront home

Chatham, Massachusetts, United States

Summary:brbrJust 1.5 miles to Main Street Chatham, AC and newly finished basementbrbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company. brbrbrbrEnjoy the serenity of Lover's Lake at this waterfront property and one of Chatham's tucked away gems. With waterfront views from almost every room in the house it's impossible to not immerse yourself inside and out in the beautiful nature that surrounds you at this home. With quick, private access to Lover's Lake it makes it easy for everyone to enjoy swimming, kayaking and sunbathing right at the tip of your fingers. No beach lines or dragging all your beach gear long distances with this kind of access to water right in front you. brbrbrbrOn the first floor of the home you are able to enjoy a spacious waterview livingroom, a dining room and fully equipped kitchen for entertaining your whole vacationing group. There are two large sliding doors to access the large deck off the living room. The large deck offers seating and a small table so you can enjoy lunch and sunset with a view. There is another small private deck off the dining room on the first floor that also has a large sliding door again opening up to 180 degree views of the lake. All the decks have twinkle lights that surround it's perimeter making the outdoor living experience at night extra magical.brbrbrbrThe first floor includes the primary King bedroom with a sitting area, TV, private deck access with seating for two, cathedral ceilings and a half bathroom ensuite. The 2nd first floor bedroom has expansive views of the lake, desk for work, and a twin trundle bed. The second floor has two additional bedrooms and a full bathroom. Both bedrooms have queen size beds, desks for remote work and are lake-facing, each with their own deck access. One queen bedroom is also equipped with a TV.brbrbrbrOutside in the backyard you will find multiple level patios all lake-facing. The main patio has a large dining table, seating, firepit and grill for optimal outdoor living. The center of Chatham is only 1.5 miles away and is a quick drive into town for dining, additional entertainment and a quaint little main street full of quintessential Cape Cod shops. brbrbrbrNewly finished basement with lounge area by the fireplace, an entertainment center with a 50inch TV, sectional seating and table tennis. A workout room with eliptical, treadmill and weight machine is available for your use. Laundry and an additional half bath complete this level. Direct access to the lower patio, lake and outdoor shower!brbrbrbrLayout of Bedrooms & Bathrooms:brbrFirst Floor brbrBedroom 1 - Twin with trundlebrbrBedroom 2 - (Primary Bedroom) King bed and 1/2 ensuite bathroombrbrFull Bathroom with walk in shower brbrSecond Floor brbrBedroom 3 - Queen bed brbrBedroom 4 - Queen bed brbrFull bathroom with standup shower brbrLower Level Finished Basement brbrhalf bathbrbrbrbr**Typically renters bring their own sheets, towels etc. Please inquire if you are interested in having linens delivered to the home for an additional fee.**brbr***We welcome approved low-impact DOGS - TENANT must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation. We will need to know the following information:brbrbrbr*Any shedding brbr*Any issues with accidents - urination or throwing up brbr*Any issues with chewing furnishings brbr*Barking while unattended or while attended brbr*Does your dog receive flea and tick preventative brbr*Are you confident you can leave property with no sign of your dog when you check out brbr*Do you accept full responsibility for the behavior and impact of dogs in your group during your stay brbrbrbrOther Things to Note:brbr-
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(25)

$535.63

/ Nightly
Private Vacation Home

Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!

Chatham, Massachusetts, United States

Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely place in South Chatham is our new second home. We simply fell in love with our place due to its beautiful placement on Mill Pond. In season, we only make our place available a few weeks a year. Because we love our new second home, we meticulously take care of it and hope to provide a personal experience that the other major rental corporations on Cape Cod cannot provide. brbrbrbrbrOur home is a 3-story Colonial Cape style home with 4 bedrooms and 2.5 bathrooms located on Mill Pond in South Chatham. What truly differentiates our home from others on Cape Cod is our own private small beach and a patio overlooking Mill Pond. Mill Pond is a small private pond with no public access which keeps this area particularly clean and peaceful throughout the season. brbrbrbrbrThe top floor includes two bedrooms: a master bedroom with king sized bed, walk in closet and very large ensuite bathroom with shower and a second bedroom with double and twin beds with ensuite bathroom with a tub/shower combination. The main floor includes a patio, living room, dining area with sweeping pond views, kitchen and half bath. Finally, the ground or above ground basement floor includes the laundry and two bedrooms which have a queen bed or a double bunk bed respectively. The bedroom with the queen bed includes a patio door with outdoor shower access. brbrbrbrbrOther amenities included with our home are central AC, a full washer and dryer, a new Weber Barbeque on our patio, a fire pit with Muskoka chairs, outdoor shower with hot and cold running water, high speed wireless internet and the premium Xfinity TV package on both TVs in the house. For use on the pond we have a Kayak, Canoe and an inflatable paddle board with a few life jackets provided. White linens (all purchased new for the 2023 season), bath towels, basic toiletries, dishwasher tabs and all kitchen utensils and plates will be provided to guests. brbrbrbrbrGuests will have ongoing contact with us for questions or concerns and will have the availability of a local caretaker/handyman for emergencies. brbrbrbrbrArea attractions include the quaint town of Chatham, the Cape Cod rail trail and at least 4 beaches in Chatham and Harwich within 2 miles including Red River Beach, Forest Beach, Ridgevale Beach and Hardings Beach. We are walking distance to the famous burrito shop The Corner Store and a very short distance to a large Stop & Shop grocery store.brbrbrbrbrThere are a few important disclosures about our place that guests should be aware of. There are no bedrooms on the main floor so stairs are required to get to all bedrooms in the house. This is an important consideration for guests with reduced mobility. Our place is located on main side street with some significant traffic from 7:00am-4:00pm due to a landscape supply depot down the road. There is absolutely no on street parking but our driveway can accommodate 4 cars. One of our neighbors owns a Roster which can be heard early each morning if the windows remain open. As everywhere in the Cape near ponds or in highly wooded areas like our property, occasional bugs may be present in and around the house, but most of our Anderson windows have screens to keep them out. Finally, we have a doorbell camera monitoring our front door. If you have any further questions or concerns, please message us and we will be quick to reply.
Bed 2

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Bath 2

Bath

Sleep 6

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$944.42

/ Nightly
Private Vacation Home

3BR Retreat Near Forest Beach & the Cape Cod Rail Trail

Chatham, Massachusetts, United States

Summary:brbrEnjoy outdoor fun and easy access to Chatham`s vibrant town center. Easily explore local beaches, restaurants, galleries, and boutiques.brbrbrbrThe Space:brbrTres Gallos is a bright, spacious South Chatham home designed for easy beach days and relaxed evenings under the Cape Cod sky. With 3 bedrooms, 2.5 baths, and room for up to 8 guests, it’s the perfect home base for families. The large backyard sets the scene for lawn games, cookouts, and s’mores by the wood-burning fire pit. Inside, guests will find everything needed for a carefree vacation—bikes for exploring, beach gear for a day on the sand, board games for cozy nights, and WiFi to stay connected. Driveway space is ample, making it easy to bring everyone along.brbrbrbrInside, you’ll find bright, comfortable gathering spaces anchored by a living room with a 65-inch smart TV and a wet bar. The well-equipped kitchen, complete with a center island, is ready for everything from quick breakfasts to full family dinners, with a double oven and plenty of prep space to make cooking a breeze. The layout is practical for groups, offering a first-floor bedroom with a king bed and an ensuite bathroom. Upstairs, you will find two additional bedrooms, each with a queen bed and two twin beds. On the second floor, you will also find a half bath with a stacked washer and dryer, and an additional full bathroom for added convenience. Stepping outside, you'll discover a peaceful, fenced-in backyard where dogs and kids can run freely. The outdoor space also boasts a patio with an outdoor dining table, perfect for grilling and dining al fresco as you linger under the stars while the fire crackles and the Cape air cools.brbrbrbrFrom this central location, you’re near the best of Chatham and the Lower Cape. Forest Beach on Nantucket Sound is just a mile away, while Ridgevale, Harding’s, and Chatham Lighthouse Beach are a short drive—perfect for swimming, long walks, and unforgettable sunsets. Hop on the nearby Cape Cod Rail Trail for a scenic bike ride toward Harwich, local ponds, or downtown Chatham. Visit the Chatham Pier Fish Market for classic harbor views and seal spotting, then cap the day with dinner along Main Street or a summer ballgame with the Chatham Anglers at Veterans Field. Book your next Chatham getaway today! brbrbrbrLayout of Bedrooms & Bathrooms: brbrbrbrMain LevelbrbrBedroom #1 - Primary bedroom with a king bedbrbrbrbrBathroom #1 - Half bathroombrbrBathroom #2 - Primary ensuite with a soaking tub and walk-in showerbrbrbrbrUpper Level brbrBedroom #2 - Queen bed and two twin bedsbrbrBedroom #3 - Queen bed and two twin bedsbrbrbrbrBathroom #3 - Full bathroom with a tub and shower combobrbrbrbr***We permit guests to bring one low-impact DOG*** - TENANT must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation. No other types of pets (cats, ferrets, etc.) are permitted. We will need to know the following information:brbrbrbr*Is he/she at least 1 year old brbr*What breed is the dog and how many pounds brbr*Any shedding  brbr*Any issues with accidents - urination or throwing up  brbr*Any issues with chewing furnishings  brbr*Barking while unattended or while attended  brbr*Does your dog receive flea and tick preventative brbr*Are you confident you can leave the property with no sign of your dog when you check out brbr*Do you accept full responsibility for the behavior and impact of dogs in your group during your stay brbrbrbr**Linens and towels provided.**brbrbrbrOther Things to Note:brbr-
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(1)

$734.61

/ Nightly
Private Vacation Home

Newly updated home sleeps 7, AC, free WIFI, half mile to town

Chatham, Massachusetts, United States

3 Bedroom - 2 Baths - Sleeps 7brA 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brGuests can bring their own linens or rent from our Linen Service for an extra fee (Bed Sheets, Bath, Beach and Kitchen Towels)brWe offer a 4 pm Check-In and 10 am Check-OutbrbrNew to VRBO! Newly updated, modern coastal ranch style home sleeps 7 - Central A/C, open concept living, free WIFI and less than a mile to town! Welcome to The Hideaway! Come stay and play with us!brbrOwners Share Why I Love My Home:brWe spent the summer of 2020 as a family at the Hideaway - the silver lining of a challenging year was certainly the memories made at our home. Our young daughter was entertained every day by having the beach, playground/baseball field, and Chatham Bakery (where Grandma spoiled her with muffins) all a very short walk away. She loved running through the sprinklers in the large back yard, and attempting to play wiffle ball with her cousins. Grandpa made daily use of the bike trail, which starts just below the house. And we were able to enjoy a few date nights - with Chatham's best restaurants in walking distance, or a glass of wine/beer by the fire pit. We have wonderful memories in this house, and hope you and your family will make some too! brbrLet Us Tell You About This Home:brJust under a mile to town, this coastal Cape home is located in a quiet, family-friendly neighborhood. The completely updated Cape Cod Vacation Rental home offers all on one floor, open living with plenty of space to spread out but also enjoy each other's company.brbrThe spacious living room with two couches, fireplace with built-in bookshelves, flat screen TV is yours to relax in. Updated coastal décor throughout with dark wood floors and soothing wall colors create a relaxing environment in the open concept living space. brbrHead into the fully equipped brand new chef's kitchen which is bright and light. The kitchen offers a center island with seating for four that opens to the dining area so family meals together are made easy. Modern stainless-steel appliances, gas stove, open shelving, quartz countertops, sunken sink, updated subway tiles all work together to make an inviting place to gather, cook and talk about plans for the day.brbrTo the left is the open dining room with seating for 6 with entrance to backyard through sliders. Contemporary style dining table invites the whole family to sit for a meal and share memories of the day's escapades. brbrWorking or learning remotely A home office is off of the dining room with a twin day bed - the perfect private space to sneak away and use your laptop, have a Zoom meeting or offer to an extra guest to sleep.brbrDirectly off of the dining room is the lush landscaped backyard and patio, fire up the grill and enjoy the lovely Cape evenings outdoors. Here you will find three distinct outdoor spaces - the cushioned couch with ottoman, an outdoor dining table with an umbrella and plenty of seating and hang out in the Adirondack chairs around the gas fire pit.brbrThis home also offers a large, fully enclosed outdoor shower with both hot and cold water, utilize this Cape Cod tradition after a day of fun in the sun at the beach! brbrTo the right of the living area are Bedroom #1 - Twin bunks with dresser, nightstand, closet, chair. brHallway Bathroom #1 - Full bathroom with tub/shower. brBedroom #2 has a Queen bed with ensuite bathroom with shower, dresser, closet, 2 night stands, two lamps. A SmartTV is a perfect addition when you want to watch a movie in bed - it's not connected to cable, so remember to bring your passwords for streaming apps (Netflix, Hulu, Prime, etc.). br​​​​​​​Finally, Bedroom #3 - Queen bed, two nightstands, 2 lamps, dresser, double closet.brbrThere's a washer and dryer in basement and access to the garage to store your bikes! The Cape Cod Bike Trail / Old Colony Rail Trail starts just below the house (Note: 0.1 miles at the intersection of Crowell and Tip Cart)!brbrCome stay and play with us - close to town, beach and biking or just stay at home and relax in comfort inside or out. The Hideaway offers it all!brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrGuest Welcome Starter Bag Included: With all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability).brbrThis home has Keyless Entry for your convenience.brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brNO PETS are allowed inside or outside the home! brMax parking of cars at property: 2 - No parking on lawn anytime. brFireplaces are only available for use in the winter months with advance approval from owner. brTown of Chatham Rental Certificate: STR-403brbrAdditional Information to Assist You:brOur calendars are updated in real-time and are accurate.brDeparture cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments.brA confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. br***Linens - bed sheets, bath/dish/beach towels and bath mats are not included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brbrArea Information: *Mileage is approximatebr0.1 mile to Bike Path Access via Crowell Road-- More info on The Rail Trail can be found here: Info on Cape Cod Bike Trailbr0.9 mile to Oyster Pondbr2.0 mile to Lighthouse Beachbr3.2 mile to Hardings Beachbr0.3 mile to Veteran's Field and the playgroundbr0.3 mile to the Chatham Village Cafe and Bakerybr0.5 mile to Chatham Fish & Chipsbr0.6 mile to Sweet Tomatoes Pizzabr0.8 mile to the Chatham Fish Pier fish marketbr1.0 mile to Chatham Bars InnbrOnly .6 Mile into downtown Chatham where you will find :brbrThe Orpheum movie theaterbrSeal tours (Beachcomber tour pick up is one block from house)brShoppingbrRestaurantsbrFriday night Band stand concertsbrThe Monomoy TheaterbrPlaygroundbrPublic TennisbrChatham A's Baseball
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Bath 2

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Sleep 7

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$985.43

/ Nightly
Private Vacation Home

Luxury Chatham Escape w/ Stunning Waterfront Views

Chatham, Massachusetts, United States

Wake up to stunning waterfront views at this beautifully designed Chatham retreat. The main level features an open living, dining, & kitchen space with double sliders to a deck overlooking the water. Three bedrooms and luxe radiant-heat baths await, while the primary king offers deck access and work-from-home setup. The lower level adds a sectional, TV, game room, and laundry - all with uninterrupted water views. Just minutes to Jackknife Beach, idealic downtown Chatham, and Chatham Bars Inn.brbr Sleeping ArrangementsbrThis home comfortably sleeps up to 8 guests across multiple thoughtfully designed spaces:brbr- Primary King Suite (Upper Level): Waterfront views, private slider to its own part of the deck, dedicated work-from-home desk, and a full ensuite bathroombr- Queen Bedroom (Upper Level)br- Twin Bedroom (Upper Level): Two twin bedsbr- Lower Level: Sectional Queen Sofa bed with flat-screen TVbrbr- Bathrooms:brThe home includes 2.5 bathrooms, all finished with upscale details. Full bathrooms feature radiant heated floors, custom tile work, and luxury shower heads - offering a spa-like experience after long beach days.brbr✔ Pack-and-play available for our tiniest travelersbr✔ Linens, bath towels, and starter toiletries providedbrbrbrLower LevelbrbrThe lower level adds flexible space for relaxing and entertaining, including a TV lounge, half bath, laundry room, and a garage game room - perfect for kids, teens, or rainy days. A second slider opens to the backyard, delivering even more waterfront views.brbr Outdoor SpacesbrbrEnjoy multiple decks and outdoor seating areas overlooking the water. While there is no direct water access, the home offers panoramic waterfront views throughout, making it an ideal setting for peaceful mornings and scenic evenings. We also have an outdoor shower perfect for rinsing off after a day at the beach. br*Outdoor shower is available seasonallybrbr LocationbrbrIdeally located just minutes from Jackknife Beach, downtown Chatham shops and restaurants, bike paths, and the iconic Chatham Bars Inn. This is a prime home base for beach days, dining out, and exploring the best of the Lower Cape.brbrOther Things to Note:brbr- Waterfront views only (no water access)br- Ideal for families, groups, and remote workersbr- Multiple sliders maximize natural light and viewsbr- Quiet, scenic setting close to beaches and townbr- Guests have access to the entire home, with the exception of a locked storage closet.brbr Pet-Friendlybr- Well-behaved, house-trained dogs are welcome (2 max) with a $125 per-dog fee.brPlease note:br- This does not cover any damage or yard clean up br- No cats (due to allergies)br*Dogs must be disclosed at booking and prior to arrival.brbrℹ️ Additional NotesbrbrWhile we strive to minimize guest disturbances, we regularly maintain our home and may conduct lawn care or plowing during reservations, particularly on weekdays or during longer stays.brbrWe have installed exterior only security cameras for the safety of both guest and property. These cameras are actively recording both audio and video on all exterior entrances and side doors. Any tampering with cameras, including, but not limited to covering and otherwise disabling of these cameras are grounds for early termination of reservation with no refunds whatsoever.brbrAbsolutely no smoking inside or near open exterior doors - there is a $250 fee if this is violated.brbrFireplace is decorative only.brbrPlease note that any refunds made in accordance with our cancellation policy will be less any credit card fees.
Bed 3

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Bath 2

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Sleep 8

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Exceptional(97)

$670.35

/ Nightly
Private Vacation Home

Walk to Ridgevale Beach in 7 minutes, Central Air, Beautiful yard Fast Internet

Chatham, Massachusetts, United States

Adorable Chatham Ridgevale Beach House With Beautiful Gardens!brbrbrbr*******7 night minimum stay Saturday to Saturday*****brbrSummer by the Shore! brbr$250 cleaning feebrbrEnjoy a hotel experience in this quentisential beach house that is only 3/10 mile (7 minute walk) down the lane to the best Family Beach in Chatham. Ridgevale Beach great for kids, a snack bar, kayak and sailboat rentals available. brbrThe house has professionally maintained gardens and grounds, outdoor shower and yard offers comfortable privacy that is buffered by conservation land. Inside there are three bedrooms, TWO full baths and a washer and dryer, (2) flat screen televisions, a sound system, an open kitchen, living and dining area - simply all you need. brbrOutdoor shower and clothesline.brbrWeber propane grill and Weber charcoal grill, also has fire pit.brbrNo need to drive your car to the beach and pay to park your car, just throw your towel over your shoulder, and walk down to the beach.brbrThe Cape Cod Bike path is 1/2 mile and fresh water Schoolhouse Pond 1 mile. Three miles to beautiful downtown Chatham for Friday night band concerts, Cape Cod Chatham A's baseball games, great restaurants.brbrHas Keurig Coffee maker- Bring your own K Cupsbrbr******Bed Linens ARE Provided But Please BRING YOUR OW BATH AND BEACH TOWELS*******brbr (1) King bed, (1) Queen bed and (2) Twin bedsbr brbrbr***Beach Chairs providedbrNo petsbrNo SMOKING brbrbrbr$250 refundable Security Deposit Required
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Bath 2

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Sleep 6

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Exceptional(103)

$804.01

/ Nightly
Private Vacation Home

5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home

Chatham, Massachusetts, United States

Chatham Beach House with deeded rights to a path to Hardings Beach as well as to a path to Oyster River Boatyard. Five minute walk to the beach. Very upscale neighborhood. Five Bedrooms including a loft area with both living and sleeping area. Two bedrooms each with a king size bed, one bedroom with a queen plus twin bed and a 4th bedroom with two twin beds. There is also a queen size bed in the loft. New custom kitchen with high end appliances. Completely open first floor allows lots of interaction with family and friends.brThe house is in Chatham, which is one of the nicest towns on the Cape. 8 minute drive to Chatham center. Downtown Chatham is always bustling with people. Enjoy the Friday night band concerts in Kate Gould Park, free to all. The whole town comes. Enjoy the Cape Cod Baseball League Chatham team. The games are played on most summer nights, are free, and again, the whole town comes. Very high quality college level baseball. Enjoy the beautiful shops, restaurants, art galleries and boutiques of Chatham's very special Main Street. Chatham is biking central. You see people on bikes everywhere including the Rail Trail Bike Path. There are many historic and natural sites to enjoy including the many beaches of Cape Cod as well as the National Seashore. Take a Whale Watching boat from Provincetown or go antiquing along historic Route 6-A. And then finish the day with a great dinner at one of the fabulous local restaurants serving fresh-off-the-boat seafood. The Monomoy Theater in Chatham has great summer stock productions. You will never be bored. Come make your own memories on the Cape and in Chatham.
Bed 5

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Bath 4

Bath

Sleep 10

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