Vacation Rentals By Owner In Chatham, MA

3 Bedrooms- 2 Bathrooms- Sleeps 8brA 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-OutbrbrWelcome to Sweet Serenity! This updated home offers Central A/C, WIFI, and a fully fenced yard for your Dog. Enjoy one-level living with a spacious open floor plan, an inviting deck outside, and coastal decor. brbrOwners Share Why I Love My Home:brThere are so many things to love about our home its hard to pick just one! The one floor living and bright and airy feel to the home is so welcoming. We enjoy only being 5 mins from Harding's beach and that we are centrally located for those special Day Trips around the Cape!brbrLet Us Tell You About This Home:brAttractively furnished, impeccably maintained, and fully equipped. This 3 bedroom, 2 bath ranch-style vacation rental home is configured to happily accommodate up to 8 guests with all rooms nicely appointed with your comfort in mind. Bonus: Fresh blankets provided from the linen rental company at the start of each stay!brbrJust four steps up and you are on the deck of this quintessential cape cod cottage! Enjoy the ease of coastal living this vacation rental offers, with all rooms on one floor. Just open the door will and you will be welcomed into the spacious family room with coastal furnishings and a flat screen TV. Through the family room is the open style kitchen and dining area. With a table that seats 6 and 2 stools at the breakfast bar - you can all enjoy family meals together. brbrGet creative with recipes in the updated kitchen with gas range. In the mornings, whip up fruit smoothies in the blender, or pull out the Lobster Pot for dinner, and enjoy a Cape Cod family favorite! brbrJust off of the kitchen is a full bath with shower. Then down the hallway there is another full bath with a tub and shower, Washer and dryer and 2 bedrooms.brbrThere are sleeping accommodations for eight, two guest rooms on one side of the home and the master bedroom on its own. The family room offers additional sleeping with a queen sleeper sofa.brbrThe master bedroom features a big , comfortable king size bed, Flat Screen TV, and comfortable seating to read a book. brbrThe second bedroom comes with two double beds and flat screen TV, and the third bedroom has a queen bed and flat screen TV. brbrThere's more space to unwind in, the bright and airy living area where you'll feel instantly at home; a light and welcoming space with comfortable new furnishings and warm hardwood floors. brbrOutside, prepare dinner on the gas grill and enjoy the beautiful Cape Cod outdoors at the dining table, or swap stories on the deck's lounge while you sip your favorite libation. Gather around the fire pit with marshmallows and watch the stars come out for a perfect end to the day. There is also an outdoor shower for your convenience- Enclosed with hot and cold water. The fully fenced in yard makes this pet friendly home the perfect place for your dog to romp or your children to play safely. brbrThere's plenty to do in Chatham! It's just a short drive to Main Street - you will love the unique shops, restaurants, theaters, and parks. Make sure to go to the Band Stand Friday night at 8pm to listen to great live music. Truly a family affair - bring your blanket, chairs and enjoy a fabulous evening of music, singing and dancing. Relax at the scenic beaches perfect for sunning, swimming, boogie-boarding, kayaking, windsurfing, or sailing. If the salt water is not your thing, try one of the calm, spring-fed, glacial kettle ponds, a great alternative for young kids.brThis is unlike any average rental. Come enjoy, relax, and make memories of a lifetime!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.brbrWith 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 offers Keyless Entry for your convenience with.brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brMax parking of cars at property: 3. No parking on lawn anytime.brDOG FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. With owner approval, a second dog may be considered for an additional $25 nightly fee. A Pet Registration form must be completed upon reservation confirmation. brTown of Chatham Rental Certificate: STR-391brbrAdditional 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: brRidgevale and Hardings Beach are both 1.8 mile from the house.br0.3 Mile to Kream And Kone for ice cream and the best fried clams!br0.7 mile to Hanger B - a great breakfast eaterybr0.8 mile to the Bike trail on George Ryder Rd - More info on The Rail Trail can be found here: Info on Cape Cod bike trailsbr0.9 mile to Marion's pie Shopbr2.1 miles to the Talkative Pig for pizza and sandwiches - offering a full bar as wellbr2.1 miles to Pisces Restaurant - cozy fine dining, be sure to make a reservation!brbrOnly 2.2 miles into the town of Chatham where you will find:brThe Orpheum movie theaterbrSeal toursbrShoppingbrRestaurantsbrFriday night Band stand concertsbrThe Monomoy TheaterbrPlaygroundbrPublic TennisbrChatham A's Baseball brbr*Mileage is approximate

Your Perfect South Chatham Summer Stay!!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$672.9

brbrbrbrbrWelcome to The Chatham Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! brbrChatham Beaches-https://www.chathaminfo.com/beachesbrbrNational Seashore Beaches-https://www.nps.gov/caco/planyourvisit/guide-to-beaches.htmbrbrEnjoy this traditional, yet well-appointed 2-bedroom condo that comfortably sleeps up to 2 or 3. Complete with a full kitchen and private deck.brThe Carriage House offers an amazing combination of affordability and exceptional proximity to Main Street shopping and Chatham's beautiful Beaches. . Guests enjoy being only a 10 minute walk away from the shops and restaurants of historic Chatham Main St. area, as well as being just 10 to 15 minutes drive from Chatham's beaches. Property abuts historic Seaside Cemetery where Bobby Hackett is buried. brbrRelax and unwind in this, 1700 sq. ft., beautiful new addition to the original Chatham Bars Carriage House. Well appointed with high ceilings, antique chestnut beams, central air, fully equipped gourmet kitchen with stainless appliances, wide board, oak floors and comfortable LR with flat screen TV, cable, wireless internet. Beautiful Master Bedroom with queen bed and marble bath and flat screen TV. Twin bed in spare room with 1/2 bath. Private deck and plenty of parking. Beautifully appointed for elegant vacation, and perfect for a romantic getawa

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$812.6

Nestled in Chatham, this charming house offers 4 bedrooms - 2 queen beds, 1 full bed, and 1 twin bed. With 2.5 bathrooms and an outdoor shower. This home has a secluded feel with its large backyard yet it is steps away from Main Street and the Mill Pond. Whether you're looking for a peaceful retreat or a fun-filled getaway, this tremendous property has everything you need for a memorable stay. It's easy to see why you'll be able to unwind at our place.

4-bedroom house in charming Chatham steps from Main Street and the Mill Pond

Chatham, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$637.49

Nestled in the heart of downtown Chatham, The Cape Coddage offers a cozy retreat for mature guests seeking a peaceful getaway with quiet hours from 9 pm to 9 am.brbrThoughtfully renovated during the winter of 2025/26, we so look forward to welcoming you to this ideally located gem. brbrOffering a minimum of three day rentals, one week or multiple week stays, please message us for prompt approval of your requested dates or take advantage of our instant booking feature.brbrThe Cape Coddage, where fabulous in-town location and brand new renovation meets quality interiors and thoughtful design.brbrBrought back to better than new condition guests brwill find a modern bathroom with marble and high end Kohler Purist fixtures, a cashmere kitchen boasting quartz countertops and backsplashes, built in appliances and under counter lights as well as an under counter washer dryer for light vacation loads.brbrNew shiplap ceilings evoke a nautical feel with subtle floor variations reflecting The Cape Coddage antique origins dating back to the 1840’s. Custom woodworking, builtins and cabinetry made right here on Cape Cod by local tradesmen complete this quintessential New England experience.brbrThe Coddage On Main includes quality linens, Soft sheets and towels are provided as are bath products, coffee and tea for lazy vacation mornings, beach chairs and umbrellas.brParking:brA dedicated guest parking spot, located through the Cape Coddage side door makes unpacking a breeze. A walkability score of 10 out of 10, brand new interiors, modern upgraded conveniences, individual mini splits, proximity to beach, shops and restaurants and experienced hosts, (9+years) makes the Coddage a perfect home base from which to enjoy your stay. brSHOES: We are a shoe free home.Kindly remove shoes upon entering the Cape Coddage.brPETS:brWe LOVE our dog and know pet owners often wish to travel with their loyal companions . It is to that end that we welcome dogs to stay at the Cape Coddage ( ONLY NON SHEDDING DOGS ALLOWED ) ALL non shedding dogs MUST be approved by host on a case by case basis at time of booking. A $500 non refundable pet fee is required,no exceptions. A $500 pet damage deposit is also required, no exceptions and will be refunded upon satisfactory checkout. These charges are separate from the liability insurance that guests purchase.brOnly housebroken pets please !brThe use of potty pads is NOT permitted and will result in penalties. Any destructive pet behaviors which require additional cleaning time, repairs or replacement of household furnishings or linens will be the responsibility of the guest. Dogs must be washed off properly and free of sand and dirt before entering the Coddage or penalties will apply. The Coddage does have an outdoor shower or if you prefer DIY dog washing options are located at Hot Diggity in Harwich Port and Tractor Supply Company in Orleans, MA

Cottage

Full Reno 2026. In Town Home. Steps To Shops. King Bed. Full Kitchen. 2 Bdrm

Chatham, Massachusetts, United States

Bed

1

Bath

4

Sleeps

$865.76

Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate the kitchen/living room combo. Embrace the impending magic of another Cape Cod summer! Pets are allowed with specific approval. Fireplace isn't for guest use.

Newly renovated house 3 minutes to Wequassett Resort and 7 minutes to CBI.

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1688.19

Welcome to your dream Cape Cod getaway!brOur brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation.brbrInside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy. brbrbrWe want your stay to be seamless, comfortable, and unforgettable. We are available throughout your trip for anything you may need — from answering quick questions to assisting with any unexpected issues.brbrYou'll have complete privacy during your stay, but we're just a message, text, or phone call away if you need local recommendations, help with the home, or anything else to make your visit even better. Our team is committed to fast, friendly, and professional service — ensuring you can relax and focus on making memories.brbrPrime Location in Chatham — Steps to the Water and Close to Everything!brbrLocated in one of Chatham’s most desirable neighborhoods, Geranium Drive offers the perfect combination of peaceful waterfront scenery and easy access to all the charm and excitement of town. Nestled along the shores of Buck’s Creek with sweeping views out to Nantucket Sound, you’ll wake up each day to the beauty of Cape Cod's natural landscape right outside your door.brbrThis property is ideally situated just a short drive — or a pleasant bike ride — to Chatham’s famous downtown, where you’ll find boutique shopping, award-winning restaurants, coffee shops, galleries, and the iconic Chatham Squire.brSpend your days relaxing at nearby Hardings Beach (just minutes away), exploring the Chatham Lighthouse, or hopping on a boat tour to spot seals and enjoy the coastline.brbrWhile you’ll feel tucked away in your own private oasis, everything you could want — beaches, dining, shopping, and entertainment — is close and convenient.brbrEnjoy the best of Cape Cod living from this unbeatable Chatham location!brbrYou will have exclusive access to the entire home and all its amenities, including the private pool, hot tub, sauna, and game room.brbrWelcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home is a private waterfront oasis with breathtaking views of Buck’s Creek and Nantucket Sound.brbrInside, a stunning cathedral-ceiling living room provides the perfect space for relaxation and gathering. The gourmet chef’s kitchen features a massive 12-foot eat-in island, ideal for family breakfasts or evening cocktails. For entertainment, head down to the basement game room, complete with a pool table.brbrStep outside to your personal resort. The expansive deck features a sparkling private pool, a bubbling hot tub, and an outdoor kitchen perfect for summer barbecues. After a day of fun, unwind in the private sauna for ultimate relaxation.brbrEach of the spacious bedrooms offers comfort and privacy for your entire group:brbrMaster Bedroom: King bed with en suite bathbrBedroom 2: King Bed with en suite bathbrBedroom 3: Queen bedbrBedroom 4: Two twin-over-twin bunk bedsbrBasement: Twin daybed with a twin pull-out trundlebrbr*There is a Minuit noise monitor located on the back porch. It does not record any sound or video just monitors decibel level.

Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$475.53

Summary:brbr16665 - Summer Breeze: Lovely Home Near Bike Path Dog Welcome!brbrbrbrThe Space:brbrThis lovely four bedroom vacation home, located on a large lot in the beautiful seaside town of Chatham, is just the place to bring the whole family, including the dog, for an unforgettable Cape Cod vacation! brbrHop on your bicycles and head down the street to the Old Colony Rail Trail, where you can journey through this completely paved eight mile former railroad trail running from Chatham to Harwich before connecting to the Cape Cod Rail Trail. From the property, you can hop in the car and drive just a few minutes to Chatham’s beautiful, pedestrian-friendly Main Street, where you will find some of the best seafood around, not to mention the many fine shops and galleries that make downtown Chatham so unique. Spend a day at nearby Chatham Lighthouse Beach, located only half a mile from downtown or two miles from the property, where you can relax on the beach, enjoying the sun, sand, and ocean, or try climbing to the peak of the lighthouse to be treated to breathtaking panoramic views of the beach and surrounding scenery. brbrBack at the property, you will enjoy a large grassy yard; perfect for running around with the kids (and dog) and playing yard games. There is a nice deck area with a picnic table, where you can enjoy family meals outside under the blue skies, and you can fire up the gas grill for a nice BBQ as often as you’d like, as full propane tanks will be supplied. Enjoy taking morning showers in the enclosed outdoor shower.brbrInside the home, you will find a living room with hardwood floors and a flat screen TV; a great space for relaxing and enjoying movie nights with the family. The fully equipped kitchen features stone countertops, bar seating, and stainless steel appliances, with a six seat dining area adjacent. Also on the main floor are two bedrooms, one with a queen size bed and the other with a twin single and twin trundle, as well as a full bathroom with a tub/shower combo. Walk up the stairs to the second floor to find the other two bedrooms, including the master with a queen size bed and en suite full bathroom with a tub/shower combo, and the last bedroom with three twin singles. Other amenities include a smart lock for easy self check-in, window A/C units in the bedrooms, a washer and dryer in the basement, and sheets and bath towels provided to all guests at no extra cost with beds made upon arrival.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 Floorsbr-1,680 Sq FtbrBedroomsbr-Total 4br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Twin Bed w/ Trundle (2 twins total)br-2nd Floor Bedroom: 1 Queen Bed w/ en suite Full Bathroombr-2nd Floor Bedroom: 3 Twin BedsbrBathroomsbr-Total 2br-1st Floor: Tub/Shower Combobr-2nd Floor: Full Bath w/ Tub/Shower Combo (en suite Queen bedroom)brOther Amenitiesbr-Fully Equipped Eat-In Kitchen w/ Bar Seating & Dishwasherbr-Window A/C Units in Bedroomsbr-Fireplace NOT for guest usebr-WiFibr-TVbr-Smart Lock/Self Check-Inbr-Driveway Parking for 3 Carsbr-Washer/Dryer (basement)br-Outdoor Showerbr-Deck w/ Furniturebr-Gas Grillbr-Large Private Yardbr-Next to Old Colony Rail Trailbr-1 Mile to Downtown Chathambr-2 Miles to Chatham Lighthousebr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrbrbrbrThe Neighborhood:brbrOceanside

Lovely Home Near Bike Path Dog Welcome!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1502.16

Spend your Chatham vacation at the POOL! This wonderful home is just minutes to everything downtown Chatham has to offer, and features a luxurious saltwater pool. Walk to swimming at Oyster Pond, shopping along Main Street as well as the Friday Night Band concerts and Chatham A's games. There is plenty of living space, with two living areas and large back yard. Sit out on the front porch with your morning coffee before you head out to the beach. The private back yard offers the pool, and backs up to Chase Park, a very quiet park great for walking your dog. It also has extra parking if you wish to have friends over (our driveway accommodates about 4-5 cars). The three bedrooms are far apart from each other: the master is upstairs, the twin set is downstairs, and the third bedroom is above the garage. This lovely home has it all!brbrFour Air Conditioning Units: 1 in each bedroom and in the dining roombrSleeps 12: 1 King, Two Queens, Two Twins, and one queen pullout sofa bed. You Can bring airbeds as well! brThis is a 3 bedroom, 2.5 bath rental.brOne full bathroom in master bedroom brOne full bathroom off of the kitchen brOne half bathroom is connected to the twin room off of the dining room. brSecond large bedroom has no bathroom connected to it. brDistance To Town: 1/10 milebrDistance To Beach: 4/10 mi. Oyster PondbrIt is equipped with a washer/dryer and included detergent.brAll amenities included, but NO food provided. (coffee maker, appliances, kitchenware, paper towels, linens, propane etc) so please bring own coffee, groceries etc. brFire pit and wood (located under the back porch) with skewers for s'moresbrWeber Grill with propane providedbrPool toys & beach toys providedbrAll linens and towels provided. brHeated and lighted Pool (kept at 80 degrees) brbrCheck in 3pm (can sometimes arrange for earlier check in) brCheck out 10 am brbrTHE PRICE IS NOT NEGOTIABLE UNLESS YOU ARE A REPEAT RENTER

Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$2240.98

Welcome to the SeaGlass House!brbrCharming and bright, open concept Cape house perfect for creating long lasting memories. Beautiful sunsets over Stage Harbor and views to the open ocean. Spacious 4 bedroom, 3.5 bath reverse floor plan home. Master bedroom and gourmet kitchen with two living spaces on the second floor to enjoy the incredible views. Gourmet kitchen has 2 subzero refrigerators, Wolf oven and cooktop along with marble countertops. 3 additional bedrooms on the main floor along with a main floor family room. 3 flat screen TVs throughout the home. Wrap around porch on the main level and two decks on the upper level. brbrAccess to private beach and walk to Lighthouse Beach in minutes as well as walking distance to Monomoy Nature Reserve.brbr

SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$524.83

Pet Friendly! Two bedroom luxury vacation condo on second floor of home in the heart of Chatham Village! Head up the stairs to find a lovely deck with cafe table and gas grill. Open the door to your little piece of heaven: the open floor plan boasts a gourmet kitchen, including a breakfast bar for 2 and a table that seats 4, skylights, living area with flat screen TV, DVD, high-speed internet access, and central air. There are 2 master suites: one on each side of the living area-offering privacy to the occupants. Both offer bathrooms with showers. The first suite has a King size bed and the larger 2nd suite has 2 Queen size beds. Walk to Chatham village and the local beaches: Andrew Hardings, Lighthouse and Claflin Landing! Kayak or canoe in Mill pond-just a couple blocks from the condo. 2 parking spaces available.brbrArea Info:br365 feet to Monomoy Coffee Company and 800 feet to the Chatham Squire!br.2 mile to Kate Gould Park where you can enjoy a bandstand concert on Friday nightsbr.6 mile to historic Chatham Bars Inn offering a beach bar, a full service spa, and fine dining all open to the publicbr.7 mile to beautiful Lighthouse Beachbr.9 mile to the Chatham Fish Pier where you can eat fresh seafood and watch the fishing boats come inbr1 mile to public golfing at the Chatham Seaside Links!brbrOwners, Allan & Eliza, occupy lower part of house and have a very friendly bernadoodle, Keara.brbrC0117970550br

Condo

Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham

Chatham, Massachusetts, United States

Bed

Bath

6

Sleeps

$990.77

Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot. Master suite on first floor with king bed. There are 1 king and 2 doubles upstairs. Basement has a ping pong table for those rainy days. Central Air! Great location for walking and biking with the family. Just a short drive to the beach. Enjoy your morning coffee in the quiet backyard on the patio, and after a long day at the beach come back and shower in the outdoor shower. Grill up a nice dinner before heading downtown shops and restaurants. Welcome bag included-Reusable tote with paper and cleaning products compliments of the owner. Dog friendly-1 dog max-$150 fee will apply. Call us at Chatham Rentals and let us help you plan your stay.

Pet friendly and spacious home in quiet neighborhood!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1367.07

This home is professionally managed by Pretty Picky PropertiesbrbrLuxurious Chatham Home, Heated Saltwater Pool, Newly RenovatedbrbrRents Friday to Friday during peak seasonbrLinens Included. Beds made.brSleeps 12brPool & Hot Tub open from Memorial Day to Columbus DaybrbrBe one of the first to stay in this masterfully renovated home with a brand-new saltwater pool under a mile (.7 mile) to Ridgevale Beach in Chatham. The 5-bedroom home plus bonus room has been totally updated from top to bottom and features brand new furniture throughout. The focal point of course is the custom saltwater pool with a built-in hot tub. The outdoor living space is stunning with an expansive travertine patio, plenty of lounge seating and an outdoor kitchen set up with a grill and granite counter. Don't forget to use the outdoor shower after the beach!brbrInside, the attention to detail is evident from the coffered ceilings to custom local art on the walls. The main living area is open to the kitchen and dining area. The kitchen is of course fully equipped with all you'll need to prepare any meal. The main level is also home to the primary bedroom with a King-sized bed and exquisite private bathroom. There are two additional bedrooms on the main level: one with a queen and one with 2 twins. There is a full bath for these rooms as well. Finally there is a second vaulted living area with additional lounge seating and a TV.brbrUpstairs features a classic Cape set up with a full bathroom at the top of the stairs. There are bedrooms on either side. Both bedrooms feature custom ship-lapped walls and ceilings and have King beds with a twin trundle.brbrEven more living space awaits on the fully finished lower level! There is another TV lounge area plus a workspace and an exercise area. There is a flex sleeping area down here which houses 2 queen beds. A brand-new full bath on the lower level completes the space.brbrA 15 minute walk or a very short bike ride brings you down to one of Nantucket Sound's most desirable beaches: Ridgevale Beach. Relax on the beach, have the little ones play in the creek flowing into the Sound and grab a bite to eat at the snack bar. A 6-8 minute drive brings you to both Chatham and Harwich Port Villages for pedestrian friendly shopping and dining. There are ample dining and shopping opportunities along Route 28 closer to the house as well. brbrPlease enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrThis property offers a 3-night minimum outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Lower Cape Cod.brbrIt's your vacation. Get Picky! ® brbrTown of Chatham Registration #STR-562

Eileen's Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$643.05

Your Chatham adventure begins at this lovely 3-bedroom house. With 2 queen beds and 1 full bed, it's the perfect retreat for guests seeking a terrific getaway. Immerse yourself in the marvelous surroundings and enjoy the comforts of heating, a washing machine, and WiFi. The 2 bathrooms provide convenience for everyone. Whether you're exploring the charming city or relaxing in the cozy living spaces, this property offers a delightful experience. We look forward to welcoming you to our place.

Walk to downtown Chatham!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$591.33

Fantastic location! Thoughtfully updated with all new furnishings! Beautiful light filled 2 bedroom, 2 bath second floor condo with outdoor shower in charming downtown Chatham. Open floor plan with gourmet kitchen, granite countertops, bar seating and separate dining table. Comfy, inviting living room with vaulted ceiling, skylight & French doors leading to a spacious deck. Central air, cozy wood stove, laundry, soaking tub & wide pine floors throughout. Linens provided!brbrRelax among the tree tops and listen to the birds with your morning coffee. Rinse off in the private outdoor shower after a day at Chatham Light House Beach. Enjoy relaxing in the Adirondack chairs with a cocktail at sunset or grill outside & dine alfresco. Professionally landscaped with attention to detail. Huge elevated deck with plenty of seating, fenced-in yard with swing set. Dogs considered with owner approval.brbrLess than five minute walk to Chatham A's baseball field & playground, bandstand, bike trail, Village Market, French bakery, DelMar Bistro, Chatham Cheese Shop & The Red Nun. Five minute walk to downtown shopping, restaurants, movie theater & Oyster Pond. Five minute drive or 20 minute walk to Light House beach. Close to everything Chatham!brbrMany happy guests with return bookings. Read the reviews!

Condo

Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1449.59

Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area and 1 1/2 baths. Also has a murphy bed for an extra person to sleep. The pool and fire pit make it a vacation you will never forget. The yard goes beyond the pool for games and fun. We are looking for people who will treat this home as if it were theirs. Just a short drive to town and the beaches.

Perfect House to Enjoy Family & Friends!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$251.79

This true Cape Cod cottage is ideal for a couple. Located in a 6 acre private community on beautiful White Pond. It is newly renovated with a kitchen/ living area, one bedroom with 2 twin beds and a large sun room/screened-in porch overlooking a colorful garden. It is complete with 2 cable TV's, VCR and fans in every room. The fresh water pond is clean and perfect for swimming and fishing! Tennis, golfing, antiquing, flea markets, art fairs, home of the Chatham Anglers (free Cape Cod Baseball League games), Friday night Chatham Band concerts (free and don't forget the penny candy store), 4 star resort Chatham Bars Inn, fine dining to carry out and everything in between, sailing, whale watches, seal watches, deep sea fishing, and the town movie theater! Don't forget a tour of Chatham Lighthouse. Close to fabulous National Seashore beaches and home to its own favorites Hardings Beach, Ridgevale Beach, and Chatham Lighthouse Beach (1.5 miles away). This a quiet hideaway away from the bustling world yet close enough for all of the activities of the charming town of Chatham.

Cottage

Delightful Cottage for Two

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$403.06

Tucked away on a quiet residential dead-end road, this charming and pet-friendly Cape-style home offers a relaxing retreat close to nature and classic Cape Cod attractions. Located near two freshwater ponds and just a short drive to Pleasant Bay, the setting is ideal for guests seeking both tranquility and easy access to beaches and outdoor adventures.brbrRecently updated, the home features a beautifully renovated kitchen, refreshed bathrooms, and updated dining areas that blend modern comfort with coastal charm. With four inviting bedrooms and two full bathrooms, the home comfortably accommodates up to eight guests.brbrThe first floor includes a fully equipped kitchen, a cozy living room, a formal dining area, a full bathroom, and two bedrooms—one with a queen bed and another with two twin beds—making it especially convenient for multi-generational stays. Upstairs, you’ll find two additional bedrooms, one with a queen bed and the other offering a full bed plus a daybed, along with a second full bathroom featuring a tub/shower combination.brbrOutdoor living is a highlight of this home. Enjoy your morning coffee or evening meals on the spacious deck, complete with outdoor furniture and a charcoal grill for summer barbecues. After a day at the beach or ponds, rinse off in the enclosed outdoor shower—a favorite Cape Cod convenience. Additional amenities include central air conditioning, WiFi, and a washer and dryer, ensuring a comfortable and carefree stay for both you and your furry companions. With its peaceful location, thoughtful updates, and welcoming atmosphere, this home is a wonderful choice for your next Cape Cod getaway.brAn administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

Pet friendly home with central air (1998)

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$413.93

You will love Rhododendron House -- a recently updated 2 bedroom vacation house. This private hilltop retreat is located 3/10 miles from one of Chatham's most popular family beaches, Hardings Beach. The short walk saves you $20 a day in beach parking fees! Newly painted inside and out, the house comes fully equipped with beach chairs/coolers, grill, bikes, two kayaks, outdoor shower and washer/dryer. Recent renovations include new Master Bedroom with King Size Bed, entirely new kitchen and patio deck. Main Street in Chatham is less than 3 miles from the house and has outstanding shops, restaurants, art galleries, parks, band concerts, baseball games and a library that has summer programs for the whole family. Come enjoy a comfortable stay in Chatham and fall in love with our wonderful town on the elbow of the Cape. brbrbrNearby Attractions: Bike and walk on the Cape Cod Rail Trail. Cape League baseball is in full swing from mid June to the first week in August. Visit the playground, wonderful art galleries, bistros, antique shops, nautical stops and candy shops. Keep an eye out for Sharks in the Park or Whales in the Park. Watch the Chatham fishermen unload their boats at the local fish pier, and enjoy some of the best fresh caught local seafood in New England. Visit the historical Chatham Lighthouse. Fresh water and salt water fishing along the shoreline. There are thousands of seals that are easily spotted along the ocean front, especially from the Chatham Fish Pier. Seal tours are available. Great White Sharks are around off the Chatham Coast as well.brbrRestaurants: There are a variety of restaurant choices available in Chatham, as well as in the neighboring towns of Harwich, Brewster and Orleans. The best seafood on the Cape is available right in downtown Chatham.....brbrFishing: Some of the finest fishing can be found on Cape Cod. We can provide you with a number of fishing spots and local fishing Charters. Chatham is THE destination for World Class Bluefin Tuna and Striped Bass Fishing. The cool waters off the Cape Cod elbow make this a prime destination for multiple game fish. Whales are also abundant, just off the coastline.

Charming Chatham Beach House; Walk to Hardings Beach

Chatham, Massachusetts, United States

Bed

1

Bath

5

Sleeps

$2137.03