Vacation Rentals By Owner In Chatham, MA

$502.01

4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**

Chatham, Massachusetts, United States

My family and I live full time in Lexington, MA. We decided to purchase our first vacation home in Chatham, MA in 2008. While the main reason was the proximity to our home near Boston, we also realized how much Chatham reminded us of our time on Nantucket Island. Chatham has all the charm and beauty as Nantucket Island, which is where we married. This was our first purchase and because of the experience, quality of life, great memories and including the fantastic year-round vibe, we decided to purchase an additional property and begin our long-term investment in the town and surrounding area. This property with its nautical theme and original refurbished floors, will provide a unique experience for guests that want to have some privacy from the downtown crowds but also be within a mile of Chatham Harbor, Chatham Bars Inn and Downtown Chatham Center. brbrBeautiful year-round vacation home with finished hardwood floors throughout and a beautiful tile bathtub & shower off the master first floor bedroom. The kitchen has nice finished wood countertops with all the appliances. Includes year-round Heat and A/C throughout on those humid days/evenings! Two bedrooms up and two bedrooms down!brGiant deck in fully fenced in backyard takes full advantage of both sun and yard area. Spring, summer & fall seasonal ping pong table, above ground firepit, volleyball net, and fenced in hot/cold outdoor shower. brBeach chairs (6+) and bikes (2+) brInclude cooler/wheels and beach trolley (other kids beach items) Huge stainless-steel grill (direct gas hookup) on backyard brick porch. brSpring/Summer garage loft open (no HVAC) for guest overflow or just kids that want some extra privacy!brbrWe have five property's in Chatham, MA at ChathamVacationProperties.com brbrWhile Linens/Pillow Cases & Towels are NOT included – We DO provide pillows, blankets, toilet paper, paper towels, dish detergent, hand soap and laundry detergent! brLinen’s, Towels and Pillow Cases can be delivered to property and picked up at property by two established businesses that are affordable: Cape Cod Linens and The Furies Online (Google for latest contact info )br

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$598.7

/ Nightly

Condo

Direct Private Beach Access (2290)

Chatham, Massachusetts, United States

Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offers not only stunning water and beach views but also exclusive access to a private association Cape Cod beach facing the renowned Outer Beach, just 100 yards away. Located moments from downtown Chatham, this charming condo fulfills your vacation checklist with direct private beach access and proximity to the vibrant offerings of Main Street.brbrThe first floor unveils an open living plan featuring a family room, dining room, kitchen, and a recently renovated full bathroom with a shower, along with the convenience of a washer/dryer. Step through a sliding glass door from the dining area to an outdoor haven with a gas grill and a table for al fresco dining.brbrAscend to the second floor to find two spacious, sun-soaked bedrooms adorned with high, airy ceilings. The primary bedroom, complete with a queen bed and a dedicated workspace for remote endeavors, opens to a deck with sweeping views of the water and the Outermost Harbor Marina. Savor a beverage at the high-top table (seats 4) or unwind in one of the 2 loungers while relishing the picturesque sunrise or sunset. The second bedroom features a full over full bunk-bed with a twin trundle bed and offers both water views and a charming vista of the Chatham Lighthouse.brbrShort getaways available with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive nights. Parking strictly limited to two cars (overage could be subject to being towed at car owners expense). An administrative fee and applicable taxes may apply. Indulge in a vacation that seamlessly blends coastal luxury, natural beauty, and urban convenience. Linens not provided. Guests may rent linens or bring their own.

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$680.24

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Private Vacation Home

Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!

Chatham, Massachusetts, United States

Summary:brbr16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!brbrbrbrThe Space:brbrIn this Quintessential Cape, your vacation dreams become a reality, offering a blend of outdoor adventures, and vibrant local culture. Nestled in the heart of Chatham, this charming vacation rental is your gateway to relaxation. A direct path from the home to the rail trail was recently cleared. Chatham Pier and Chatham Lighthouse Beach, both just a short drive away at 1.6 miles and 2.5 miles respectively, beckon with their coastal beauty, promising unforgettable experiences. brThis home embodies the natural Cape spirit, bathed in light with bright, cheerful colors that infuse every corner with warmth and vibrancy. An open layout welcomes you, inviting you to unwind and savor the moments of your vacation, or weekend getaway! brbrNature enthusiasts and dog lovers will find their haven right in the backyard, where the Old Colony Rail Trail awaits. Whether you prefer a leisurely stroll or an exhilarating bike ride, this scenic path promises unforgettable adventures.brbrStep outside to your private outdoor patio space, equipped with propane grill, a perfect spot for al fresco dining and making cherished memories under the open sky. As the sun settles below the horizon rejuvenate yourself in the outdoor shower and cool down before your evening plans. When you're ready to wind down for the evening, Inside are 4 spacious bedrooms with comfort amenities for the whole family. brbrWhen it's time to savor local flavors, head to the beloved Chatham Squire, a mere 1.4 miles away on Main Street. Delight in dinner and drinks, and after your meal, explore the charming shops and candy stores that line Main Street, adding a touch of whimsy to your Cape Cod evenings. Secure your stay today and immerse yourself in the Cape's timeless charm.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 FloorsbrBedroomsbr-Total 4br-1st Floor Bedroom: 1 Queenbr-1st Floor Bedroom: 2 Twin Bedsbr-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 2br-1st Floor: Full Bathroom w/ Shower/Tub Combobr-2nd Floor: Full Bathroom w/ Shower/Tub CombobrOther Amenities br-Central ACbr-WiFibr-TVbr-Washer/Dryerbr-Propane Grill br-Outdoor Showerbr-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0417190550brbrbrbrThe Neighborhood:brbrGeneral

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$1363.72

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Private Vacation Home

Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend

Chatham, Massachusetts, United States

Summary:brbr16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly!brbrbrbrThe Space:brbrDiscover the epitome of Cape Americana in this elegant Chatham home, a rare gem with exclusive private association access to the renowned Hardings Beach. Immerse yourself in classic, timeless furnishings that pay homage to the old-world charm of Cape Cod, setting the stage for an unforgettable vacation. With ample space for 10 guests, this three-story beach home welcomes the whole family, furry friends included. On the ground floor, a dedicated kids' room ensures that even rainy days are filled with joy, featuring an array of games to delight all ages. Upstairs, a unique king suite offers a touch of luxury, complete with a balcony that unveils breathtaking views of the shimmering waters, a perfect backdrop to create cherished memories.brbrThe main living space is bathed in natural light, creating an inviting ambiance where cooking for the family feels like a delightful adventure in the stunning kitchen. Every moment spent here is infused with the warmth of this exquisite home.brbrJust a leisurely 2-minute stroll away, Hardings Beach beckons, with easy neighborhood access a mere 200 feet from your doorstep. Spend your days soaking up the sun, building sandcastles, or exploring the charming local eateries that Chatham has to offer. (Don't forget, Hardings Beach welcomes dogs from September 16th to April 30th.)brbrIn this exceptional Chatham retreat, you'll experience the perfect blend of elegance and seaside allure. Reserve your stay today and let the tranquil waves of Hardings Beach and the timeless beauty of this home create the backdrop for your dream Cape Cod getaway.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10br-3 Floorsbr-4 Bedroomsbr-Ground Floor Open Bunk Room: 2 Bunks (4 Twin Beds)br-1st Floor: 1 Queen Bed (Ensuite Bathroom)br-1st Floor: 2 Full Beds (Ensuite Bathroom)br-2nd Floor: 1 King Bed (Ensuite Bathroom)br4.5 Bathroomsbr-Ground Floor: Shower Onlybr-1st Floor: Half Bathbr-1st Floor: Showerbr-1st Floor: Shower (Ensuite, 1st floor bedroom with two queens)br-2nd Floor: Shower and Tub (Ensuite King Bedroom)brOther Amenities br-Central ACbr-WiFibr-Cablebr-Washer/Dryer on Ground Floorbr-Propane Grill br-Please note outdoor amenities are available seasonallybr-Fireplace is NOT for guest usebr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC1965778002

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$880.24

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Private Vacation Home

Roof Deck, Walk to Forest Beach, Fire Pit!

Chatham, Massachusetts, United States

Summary:brbr16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit!brbrbrbrThe Space:brbrInn Bloom is perched on a small hillside in the charming coastal town of Chatham. This vacation rental has just the right blend of seaside elegance and timeless decor. A leisurely 10-minute walk will bring you to the shoreline of Forest Beach, where there is no shortage of fun in the sun! Forest Beach is great for families, and one of the most sought after beaches on the Cape. Upon arriving, take a deep breath in because your vacation has just started. Relax and unwind in your private outdoor space, designed for families and friends to gather and make memories of a lifetime. For those seeking the ultimate sun-soaked retreat, grab your favorite book and climb to the rooftop deck, where you can bask in the golden rays (don't forget your sunscreen!). As the day transitions into evening, reminisce with loved ones around the elevated fire pit area, where stories are shared and memories are forged under a star-studded sky. brbrThe interior of this home has been tastefully updated with classic nautical decor and artful finishes that exude coastal sophistication. Every corner of this home is lovingly decorated, ensuring a stay that is as comfortable as it is charming.brbrFor culinary explorations, you'll find an array of local dining treasures just minutes away. Start your day at Hangar B for a delightful breakfast experience and watch the planes take off! For lunch, indulge in the savory creations at Mom & Pops Burgers, a local favorite. After all of your day activities are finished, treat your palate to the exquisite flavors of Buca’s Tuscan Roadhouse, an upscale Italian gem that promises a memorable dining experience.brbrIn the heart of Chatham, Inn Bloom offers every comfort you'll need for a home away from home. With a little something for everyone, we know you'll want to come back year after year! brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 10br-3 Floorsbr-Ground Floor Bedroom: 1 Full Bed and 1 Bunk, Twin over Twinbr-1st Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 Queen BedbrBathroomsbr-Ground Floor: 1/2 Bathbr-1st Floor: Full Bath w/ Shower br-2nd Floor: Full Bath w/ Tub/Shower Combobr-Central ACbr-WiFibr-Smart TV br-Washer/Dryer br-Indoor Fireplaces are NOT for guest usebr-Wood Fire Pit (please source wood locally)br-Peloton Bike (bring your own shoes)br-Outdoor Showerbr-Gas Grill br-Please note outdoor amenities are available seasonallybr-please note there is an exterior camera on the entrance door that is not recording during the rentable seasonbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0449520550brbrbrbrThe Neighborhood:brbrWalk to Water

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$995.35

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Private Vacation Home

Spacious Home with Direct Pond Access!

Chatham, Massachusetts, United States

Summary:brbr16616 - Day Dreamer: Spacious Home with Direct Pond Access!brbrbrbrThe Space:brbrWelcome to the charming town of Chatham, Massachusetts, where the salty ocean air mixes with the sweet scent of blooming flowers and fresh seafood. And what better way to experience it all than by staying at this stunning property overlooking Ministers Pond Sit back, relax, and enjoy this Day Dreamer!br br Nestled in the heart of picturesque woodlands and lush gardens, this 2.33-acre retreat is a true slice of heaven. Stepping inside, you’re greeted by a cozy home, where you are surrounded by warm wood and natural light. The first floor living room is ready for vacation conversations and late night cocktails. The kitchen is ready for meal prep, before feasting at the dining table under the vaulted ceiling, bathed in natural light.brbrThe downstairs living room is a great space to unwind and watch your favorite vacation flick, while you immerse yourself in the surround sound audio system. brbrWhen it’s time to sleep, 6 bedrooms comfortably sleep 12 guests in this spacious retreat. Downstairs, two bedrooms, one with two twins and one with a queen bed is the perfect space for extended family. The primary bedroom features a king size bed and en suite full bathroom with jetted tub, and a large window that offers breathtaking views of the sparkling water of Ministers Pond through the trees. The second floor houses a bedroom with a king size bed and en suite full bathroom. The remaining bedrooms await your slumber on the second floor.brbrOutdoors, the shores of Minister Pond are ready for your vacation rest and fun. Enjoy a meal outdoors on the elevated deck, with an outdoor dining table and views of the pond below.brOther amenities include a washer and dryer, outdoor shower, and central A/C and mini-split A/C systems to keep you cool all summer long. A visit to this idyllic destination is the perfect way to relax, unwind, and immerse yourself in the beauty of Cape Cod, at the Day Dreamer!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 12brBedroomsbr-Total: 6br-Ground Floor Bedroom: 2 Twin Bedsbr-Ground Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 King Bed with En Suite Full Bathroombr-2nd Floor Bedroom: 1 King Bed with En Suite Full Bathroombr-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 3 full, 2 halfbr-1st Floor: En Suite Full Bathroom with Jetted Tub and Showerbr- 2nd Floor: En Suite Full Bathroom with Tub/Shower Combobr-2nd Floor: Full Bathroom with Tub/Shower Combobr-1st Floor: 1/2 Bathbr-Ground Floor: 1/2 BathbrOther Amenitiesbr-Central A/C + Split A/Cbr-Smart TV with Streaming Servicebr-Smart Lock/ Self Check-Inbr-WiFibr-Washer & Dryerbr-Outdoor showerbr-Private Yard With Gazebo and Fire Pitbr-Propane Grillbr-Please, *NO PARTIES*br-Please note outdoor amenities are available seasonallybr-Please note there is an exterior camera on the property that records driveway/entry doorbr-Overlooking Ministers Pond with Direct Water Accessbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for a maximum of 4 carsbr-C0413420550brbrbrbrThe Neighborhood:brbrOceansidebrbrbrbrOther Things to Note:brbrPlease note there is an exterior camera on the property that records the driveway/entry door

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$297.12

/ Nightly

Private Vacation Home

Old Cape Cod Charm in Chatham MA, 1/4 mile Walking Distance to Hardings Beach

Chatham, Massachusetts, United States

Quaint 3 bedroom 1 bath cottage, easy 1/4 mile walk to Hardings Beach, one of Chatham's best beaches on Nantucket sound. Enjoy warm summer beach days and cool summer nights all within a 5 minute drive to downtown Chatham one of New England's best main streets, Chatham A's summer baseball, Monomoy Theatre and countless activities.brbrLinens, towels etc are renters responsibility.brbrSunroom, outdoor area, front deck, outdoor shower, washer & dryer, cable & internet.

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$729.45

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Private Vacation Home

Located on Rail Trail By Beach & Downtown!

Chatham, Massachusetts, United States

Summary:brbr16617 - Skipping Stone: Located on Rail Trail By Beach & Downtown!brbrbrbrThe Space:brbrThis beautifully updated home is a great place to enjoy a family vacation on Cape Cod! Beautiful downtown Chatham is less than a mile away, so all the best restaurants, shopping, and entertainment are just around the corner. Not only are Lighthouse beach and Jackknife Cove just a couple miles away, this home is surrounded by ponds that are within walking distance. Emery Pond, White Pond, Perch Pond, and Lover's Lake are all half a mile or less from the house, and the Chatham Airport is just a few minutes away. The home itself is well-updated with modern appliances and plenty of room for 8 guests. The 1st floor of the home offers a living room, large sunroom, eat-in kitchen, two bedrooms, and a full bathroom. One of the first floor bedrooms offers a queen bed, while the other bedroom offers two twin beds. Upstairs there are two additional bedrooms; one has a king size bed and a crib, and the other has two twin beds. A brand new central A/C system will be sure to keep you cool on those hot summer days. The outdoor area is beautiful and offers a small deck with a gas grill and a dining area. The deck leads down into a great grassy backyard - perfect for kids and your dog to play or to relax and soak up the sun. This is a great location to experience Chatham and the surrounding areas of Cape Cod. Don't wait to book this awesome vacation home!br br brHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-Bedroom 1: 1st floor, 1 queen bedbr-Bedroom 2: 1st floor, 2 twin bedsbr-Bedroom 3: 2nd floor, 1 king bed + cribbr-Bedroom 4: 2nd floor, 2 twin bedsbrBathroomsbr-Total: 2br-1st Floor: Full Bath w/ Tub/Shower Combobr-2nd Floor: Full Bath w/ Showerbrbr-Central A/Cbr-Window Units/Floor Unit A/C in each bedroombr-Smart TVbr-WIFIbr-Washer and Dryerbr-Outdoor Showerbr-Private yardbr-Gas Grillbr-Located on the Old Colony Rail Trailbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0409420550brbrbrbrThe Neighborhood:brbrOceanside

4

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2

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8

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$812.27

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Private Vacation Home

Walk to Schoolhouse Pond!

Chatham, Massachusetts, United States

Discover this beautifully updated three-bedroom dog friendly home, located within walking distance of the beloved swimming beach at Schoolhouse Pond, just down the street from the idyllic Rail Trail biking path, and a short drive from all the charm of downtown. The house sits on an acre of land that backs up to conservation land and Goose Pond. All new appliances, including a washer and dryer, mattresses and furniture! Thoughtfully designed for comfort and relaxation, the home features two king bedrooms, a bedroom with two twin beds, and two full bathrooms. The sun-filled first floor offers an inviting and open layout with a spacious living room with a 65 inch smart TV, a dining area for family meals, and a well-equipped, brand-new kitchen with island seating; ideal for kids to enjoy breakfast before a day of adventure. Fist floor boasts a king bedroom and a full bathroom with a walk-in shower. Upstairs, you’ll find the twin bedroom, a second king bedroom, and another full bathroom with a tub. Central air conditioning keeps the home cool on warm summer days. Begin your mornings with coffee on the back patio and end beach-filled days rinsing off in the outdoor shower. The property abuts conservation land and is conveniently close to town, where you can enjoy dinners out, shopping, movies, ice cream, and even a renowned Cape League baseball game. To make your stay even easier, guests are greeted with a complimentary Welcome Bag from the owner, including a reusable tote stocked with starter paper products and cleaning supplies. New outdoor patio set and new Webber gas grill for outdoor dining and relaxing too! This inviting, dog-friendly home (one dog permitted; $150 pet fee) is the perfect place to create lasting vacation memories year after year. Contact Chatham Rentals today to reserve your stay!

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$359.09

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Condo

Chatham Village - Center - Main Street Center Area

Chatham, Massachusetts, United States

This is a fantastic - location right off main street in Chatham downtown area - 5 minute walk to Oyster Pond Ocean Inlet - right across from Chatham Village Market and one of the most popular restaurant - Del Mar! and two buildings down from the Chatham Cheese Shop! Miss the downtown traffic and enjoy 878 Main Street - Condo 878A and our lovely entire one floor living condo with plenty of windows, sun and fun! A private deck with gas grill, outdoor eating and a fantastic Professional Pool Table with Cable, High Speed Internet, Stereo, Private entrances and all wood flooring - Including Washer and Dryer. Access to private garage with bicycles and beach equipment!brbrWe have five property's in Chatham, MA at ChathamVacationProperties.com

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$583.13

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Private Vacation Home

Central AC Close to Beach Dog Friendly!

Chatham, Massachusetts, United States

Summary:brbr16613 - Maiden Chatham: Central AC Close to Beach Dog Friendly!brbrbrbrThe Space:brbrEnjoy this beautifully renovated, well appointed home for your Chatham vacation. Nautical decor adds charm and a seaside feel to this comfortable, central air conditioned home. Walk to local restaurants and shops, or drive only 5 minutes to Downtown Chatham. Conveniently located just a short drive from Ridgevale or Hardings Beach, you'll have your pick of Chatham's famous coastlines to choose from for your summer swim. After a day enjoying the sun and sea, return to a beautiful back yard for a barbeque and a great fire pit for cool evenings toasting marshmallows under the stars. This spacious home offers three bedrooms across two floors, and a lofted sleeping space with a TV and queen size futon. The downstairs hosts a game room for rainy days or anytime the mood for a quick ping pong match strikes. Book today for an idyllic Chatham vacation for you and your whole family - even the dog!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 FloorsbrBedrooms: brTotal: 3br-1st Floor Bedroom #1: 1 Queen Bedbr-1st Floor Bedroom #2: 2 Twin Bedsbr-2nd Floor Master Bedroom: 1 King Bedbr-2nd Floor Loft: 1 Queen FutonbrBathrooms:brTotal: 1.5br-1st Floor: Full Bath w/ Tub/Shower Combobr-2nd Floor: 1/2 bathbr-Central A/C on 1st Floor | Mini-Splits on 2nd Floorbr-Cable TV/Smart TVbr-WiFibr-Washer/Dryer in Basement br-Private Yardbr-Fire Pitbr-Large Patiobr-Ping Pong Tablebr-Gas Grillbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0419850550brbrbrbrThe Neighborhood:brbrOceanside

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$1165.31

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Private Vacation Home

Walk to Ridgevale Beach!

Chatham, Massachusetts, United States

Summary:brbr16612 - Salty Breeze: Walk to Ridgevale Beach!brbrbrbrThe Space:brbrThere is nothing like heading to Cape Cod and enjoying the Salty Breeze! Enjoy your coffee, sunbathing or enjoy the spectacular views all day long from the expansive wraparound deck at this lovely home. Walking distance to Ridgevale Beach and a short drive to Downtown Chatham or Harwich Port, this beautiful oasis is a perfect spot for your family vacation or weekend getaway. Complete with an updated kitchen, a sun filled living room with water views, and an expansive deck to take in the views and salty air. brThe views don’t stop in the primary bedroom, where the seagulls can lull you to sleep before waking up to glistening water views. The second bedroom houses two twin beds, perfect for the kids to crash in after a day exploring Chatham. brbrBring your kayak and explore beautiful Buck's Creek and even venture out to the Nantucket Sound for some ocean kayaking! Feel the sun on your skin and the water in your hair, at the Salty Breeze! brHome Details: brDogs Welcomed (w/fee of $45/night per dog)br-Sleeps 4br-Single Floorbr-Bedroom #1: 1 King Bedbr-Bedroom #2: 2 Twin Bedsbr-1 Bathroombr-Bathroom #1: Full Bathroom with Tub/Shower Combobr-Central A/Cbr-Cable TVbr-WIFIbr-Washer & Dryer in basement (walk out access from outside)br-Outdoor Showerbr-Private Yardbr-Propane grillbr-5 min nature walk to neighborhood beachbr-Views overlooking salt-marsh with expansive views of Nantucket Soundbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0436910550brbrbrbrThe Neighborhood:brbrOceanside

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$915.6

/ Nightly

Private Vacation Home

Walk to town and beach from this updated 3BR house in historic Chatham

Chatham, Massachusetts, United States

Recently renovated for 2025 to include updated bathrooms and new furnishings. NEW photos coming soon! A fantastic, family rental steps from Main Street and Veterans Field. Completely updated throughout and located on a quiet dead-end street, just off the beaten path. Large Master on the 2nd floor with King bed and rollaway. Huge front yard with tons of room for running and lounging around. A great spot for a family with small kids, with a small playground just off your back yard as well as the large town playground one block away! Two blocks from Children's Beach at Oyster Pond as well, you won't need your car for much of this vacation!brbrLinens and towels can be rented through Chatham Concierge. https://www.chathamconcierge.com. They deliver and pickup used linens. brbrBeach towels are included.brbrPrimary BR includes a roll-away twin and a twin pull-out for additional sleeping options. brbrNo pets.

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$434.91

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Cottage

WALK TO RESTAURANTS, SHOPS & LIQUOR STORE! CLOSE TO DOWNTOWN CHATHAM!

Chatham, Massachusetts, United States

This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 minute walk down the street brings you to White Pond. The cottage has deeded rights to the pond, for you to enjoy swimming, fishing and canoeing. It has 3 bedrooms- 1 queen bed, 2 twins and bunk beds that sleep 2. One bathroom with stall shower and sink. With a sunny open floor plan, it provides lots of living space. Washer/dryer and central air. Bed linens, bath towels and kitchen towels all included. Fully equipped kitchen is the perfect size to cook any meal and relax at home- rather than eat out. New LG stainless steel electric range for the 2025 season! Relax in the sunroom and enjoy your favorite book and morning coffee. Just outside the kitchen door is a Weber gas grill. Beach towels are here for your convenience. Plus sand toys for the kids. The landscaping is lovely with grass and mature trees. Parking for 2 cars. brTo Get to White Pond:brLeaving the cottage— walk down to the end of Balfour Court and make a left. Walk to the end of Balfour Lane, which ends in a cul-de-sac. Take the paved road on the left and down the hill, road curves to right. Stay on right. Road becomes 2 tire tracks to clearing with sign “Swimming for Balfour Residents ONLY with pond access.”brbrHouse Rules:br- Do not smokebr- Do not bring your petsbr- Be respectful of our neighbors as several live there full timebr- Dispose of all remaining food and place garbage in the outside bin before you leavebr- Place all dirty dishes in the dishwasher and runbr- Wash and dry all used linens and towels prior to check out. Do NOT wash bedspreads or pillow shams-- please leave them on the beds.brOff season: Nov-April. There will be a $60 laundry fee, as the laundry shed will be winterized. br- Return key upon departurebr- Check in- after 3pmbr- Check out by 10am

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$799.94

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Private Vacation Home

Stunning Water Views 2 Decks! By Beach!

Chatham, Massachusetts, United States

Summary:brbr16611 - Bucks Creek West: Stunning Water Views 2 Decks! By Beach!brbrbrbrThe Space:brbrSet at the end of a quiet road, this comfortable family home is an ideal setting for a classic Cape Cod getaway. With Ridgevale Beach just a five-minute walk away and only a short drive to downtown Chatham or Harwich Port, the location makes it easy to enjoy the best of the Lower Cape.brbrThe main level features a bright, open floor plan designed for easy vacation living. Two separate living areas provide space to spread out, while the well-equipped kitchen and dining area open directly to a large deck overlooking Buck’s Creek. It’s an ideal spot for barbecuing, enjoying creek views, and watching the sunset at the end of the day. A first-floor bedroom with a twin daybed and trundle with an en suite full bathroom offers added convenience and flexibility.brbrUpstairs, the second floor offers three additional bedrooms. The primary bedroom features a king bed and access to a second-story deck with sweeping views—perfect for morning coffee or quiet evenings. Two more bedrooms, one with a queen bed and the other with two twin beds, are also on this level, along with a full bathroom, completing the second floor.brbrOutdoor living is a highlight here. With easy access to Buck’s Creek, guests can bring a kayak and explore the peaceful waterways right from the neighborhood, all while enjoying the natural beauty and memorable sunsets that define Cape Cod.brbrWhether your days are spent at the beach, on the water, or exploring nearby towns, this home offers a relaxed and convenient place to return to at the end of the day.brbrHome Details: br-Dogs Welcomed (w/fee of $45/night per dogbr-Sleeps 8br-Two floorsbrBedroomsbr-Total 4br-1st floor Bedroom: 1 Daybed w/ Trundle (2 twins) w/ en suite bathroombr-2nd floor Bedroom: 1 King Bedbr-2nd floor Bedroom: 1 Queen Bedbr-2nd floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 2br-1st Floor: Full Bathroom w/ Shower (en suite Twins Bedroom)br-2nd Floor: Full Bathroom with Shower/Tub combobrOther Amenitiesbr-Central A/Cbr-Washer & Dryer in Basementbr-WiFibr-TVbr-Gas grillbr-Outdoor Showerbr-Wood Fireplace NOT for Guest Use (fines remitted)br-Large Private Yardbr-Walk to Ridgevale Beachbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0436940550brbrbrbrThe Neighborhood:brbrOceanside

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Sleeps

$307.36

/ Nightly

Private Vacation Home

Lovely Home Minutes from Beach in Chatham!

Chatham, Massachusetts, United States

Summary:brbr16605 - Sea Pine Cottage: Lovely Home Minutes from Beach in Chatham!brbrbrbrThe Space:brbrTucked into a quiet Chatham neighborhood near Bucks Creek Marsh and just steps from the Oyster River, Sea Pine Cottage offers a peaceful Cape Cod escape with easy access to some of the area’s most loved spots. Harding’s Beach is only minutes away, making it simple to spend long summer days by the water before returning home to unwind.brbrThis charming, single-level Cape is thoughtfully set up for a relaxed vacation. Inside, the home features comfortable living spaces, WiFi, a Smart TV, and all the modern conveniences needed for an easy stay. The kitchen and living areas flow naturally for shared meals and downtime, while portable floor A/C units in the bedrooms keep sleeping spaces cool and comfortable.brbrThe layout includes three bedrooms that sleep up to six guests. The primary bedroom features a queen bed, the second bedroom offers a full bed, and the third bedroom is perfect for kids with twin bunk beds and a trundle. A washer and dryer are also available for added convenience.brbrOutside, the private yard and large deck create a welcoming space for summer barbecues, or morning coffee. A gas grill makes outdoor meals easy, and the quintessential Cape Cod outdoor shower is ideal after a beach day. The quiet surroundings offer a sense of seclusion, while downtown Chatham—with its shops, dining, and harbor views—is just a short drive away.brbrSpend your days at the beach, kayaking and exploring the nearby waterways, or strolling through town before coming home to relax in a setting that feels both simple and special.brbrSea Pines Cottage is a classic Cape getaway—book your stay today and enjoy Chatham at its most laid-back.br br Home Details:br-No Pets(Fines Remitted)br-Sleeps 6br-Single floorbrBedroomsbr-Total: 3br-1st Floor Master Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Full Bedbr-1st Floor Bedroom: 1 Bunk Bed and 1 Trundle (3 Twins total)brBathrooms:br-Total: 1br-1st Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Portable (floor) A/C units in bedroomsbr-WiFibr-TVbr-Washer and dryerbr-Gas grillbr-Gas Fireplacebr-Outdoor showerbr-Private yardbr-Minutes from beachbr-NO pets (fines remitted)br-Sheets and towels provided with beds made upon arrivalbr-Cleaned with hospital grade disinfectantbrC0412950550brbrbrbrThe Neighborhood:brbrBayside

3

Bed

1

Bath

6

Sleeps

$2325.16

/ Nightly

Private Vacation Home

AMAZING NEW HOME, STEPS FROM LIGHTHOUSE BEACH!

Chatham, Massachusetts, United States

brbrbrClick for Drone TourbrbrbrRECENTLY REDUCED BY $5000 ..... NEW RATE FOR REMAINING WEEKS IN JULY AND AUGUST, $15,000 !!! brbrExperience coastal luxury in this stunning, newly rebuilt home ideally located just a short walk from both town and Lighthouse Beach. Nestled in the heart of Chatham's historic village, this beautifully renovated 5 bedroom, 5 bathroom retreat offers the perfect blend of comfort, style, and convenience.brbrEach spacious bedroom features its own private bath, creating an ideal setup for families or groups. Enjoy glimpses of Chatham Harbor, relax in thoughtfully designed private spaces, or gather together in the bright, open living areas.brbrThe home boasts a state of the art kitchen with all new appliances, perfect for entertaining, along with outdoor dining for enjoying warm Cape evenings. Additional amenities include central air conditioning, all new furnishings, high speed WiFi, and three HDTVs with streaming services.brbrWhether you're seeking relaxation or adventure, this exceptional property offers the perfect home base for your Chatham getaway.

5

Bed

9

Bath

10

Sleeps

$1084.32

/ Nightly

Private Vacation Home

Sprawling 5 BR Chatham Escape / Endless Outdoor Living & Entertaining Choices

Chatham, Massachusetts, United States

Completely renovated in 2017, this classic Cape is the perfect Chatham beach house. Offering an open flow layout with five bedrooms, the home is situated in a quiet neighborhood close to town as well as Harding's Beach. The main level features an en-suite master, an additional bedroom, a family room, an eat in kitchen and a cathedral beamed living room with fireplace, half bath and laundry hook-up. Above are three more bedrooms and a full bath. The living spaces seamlessly blend outdoors with a large outdoor patio and nearly a half-acre of yard space. The whole family will love the out-door space with fire-pit and corn hole as well as a Foosball table! It features plenty of upscale outdoor furniture too!brCentral Air, Wireless Internet, Gas and Charcoal Grill and 2 Smart TVs: Master BR and Family Room

Bed

Bath

Sleeps

$1029.14

/ Nightly

Private Vacation Home

Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!

Chatham, Massachusetts, United States

Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham! Experience beautiful water views with your morning coffee, and coral colored sunsets while grilling up your dinner on the back deck. Sit on the Farmer's Porch and sip a cold drink with a good book. This charming home offers a bright and airy 1st floor open living space with kitchen and dining areas, and sliders to the wrap around deck. This 2 bedroom home has 2 queen beds, and 2 twin beds in the finished basement. Walk to Chase Park, Oyster Pond Beach and downtown for all of your shopping, dining and entertainment. Central a/c to keep you cool on those hot summer days, and Wi-Fi to keep you connected. Enclosed outdoor shower to rinse the salt and sand off after a day in the surf. Perfect house and location for a Cape Cod getaway. This rental shares a driveway and there is another property next door. Call us at Chatham Rentals and let us help you plan your stay.

Bed

Bath

Sleeps

$873.25

/ Nightly

Private Vacation Home

Enjoy your own private pool in Chatham! (2252)

Chatham, Massachusetts, United States

Experience the ultimate in coastal luxury at this uniquely designed property in historic South Chatham. Perfect for large families, multi-generational groups, or two families traveling together, this property comfortably accommodates ten guests across two distinct living quarters. Separated by a two-car garage, this clever layout offers the rare gift of togetherness balanced with complete privacy.brbrThe main residence is a study in graceful Cape Cod living. The first floor flows effortlessly from a fully equipped chef’s kitchen into a formal dining room, leading to a spacious living area featuring a queen sleeper sofa and a large TV for movie nights. This level also includes a versatile bedroom with a full futon, a full bathroom, and a convenient laundry room. Upstairs, you will find three beautifully appointed bedrooms—two featuring king-sized beds and a third with two twin beds—alongside a well-placed half bath.brbrJust steps away, a separate private entrance leads to an expansive additional living suite. This self-contained retreat is impressively equipped with its own full kitchen, a bright king bedroom, and a modern bathroom with a walk-in shower. The large, open-concept living and dining area abuts a grand back deck that overlooks the property's crown jewel: the private, fenced-in pool.brbrThe outdoor experience at this home is truly spectacular. Follow the meandering slate path through manicured green lawns to reach your private poolside sanctuary, surrounded by pristine landscaping. Whether you are lounging on one of the two spacious decks, firing up the gas grill for a summer barbecue, or engaging in a friendly game of shuffleboard or cornhole, the backyard is designed for making memories. Two outdoor showers provide the classic Cape experience of rinsing off under the sun or stars.brbrIdeally located in South Chatham, you are just a short drive from the region's most beautiful beaches and the charming boutiques and eateries of the village. Modern comforts such as central air conditioning and high-speed WiFi ensure a seamless stay.brbr Short getaways available with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive nights. Please note: pool use is seasonal, not guaranteed outside peak summer months, and subject to routine testing and maintenance. An administrative fee and applicable taxes may apply. brbr**Linens not provided. Guests may rent linens or bring their own.**

4

Bed

2

Bath

10

Sleeps

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