Home Vacation Rentals By Owner In Chatham, MA

Showing 400 Of 420 Vacation Rentals
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Exceptional(12)

$1223.47

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Private Vacation Home

Luxurious Home with Pool & Game Room in Cape Cod

Chatham, Massachusetts, United States

Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven for relaxation and entertainment, making it the perfect choice for your getaway. With its stunning backyard overlooking a heated pool and conservation area, you'll find yourself surrounded by lush greenery and the soothing sounds of nature.brbrWake up to the harmonious melodies of chirping birds as you savor your morning coffee on the deck. The backyard oasis beckons with a heated swimming pool, complete with floats and comfortable lounge chairs, inviting you to take a refreshing dip or simply bask in the sun. Unwind in the outdoor shower after a day of exploration or fire up the outdoor grill for a delectable barbeque feast.brbrStep inside and discover the epitome of comfort and luxury. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and ample space to unleash your culinary creativity. Share meals with loved ones in the spacious dining area, or gather in the cozy living room to relax and enjoy quality time together.brbrEntertainment options abound in our home. Indulge in a cinematic experience in the home theatre, boasting a 70-inch TV for immersive viewing pleasure. The dedicated kids' video game area ensures endless fun for the younger guests. For friendly competition, challenge your family and friends to basketball, foosball, cornhole, or ping pong. And when you're in the mood for a quiet evening, our extensive collection of board games promises hours of laughter and bonding.brbrBeyond the comforts of our vacation home, you'll find yourself in the enchanting town of Chatham. Immerse yourself in its vibrant atmosphere, with great shopping and dining options that cater to all tastes. Explore the picturesque beaches and indulge in the tranquility of the ocean. Embark on a biking adventure along the scenic trails, allowing you to soak in the natural beauty that Cape Cod is renowned for.brbrBook your stay at our new vacation home in Chatham and experience a memorable getaway filled with relaxation, entertainment, and the charm of this fantastic town. Don't miss out on this exclusive opportunity to create cherished memories with your loved ones. We can't wait to welcome you!brbrPlease note: Amenities and availability may vary depending on the season. Additional fees and restrictions may apply. Please check the listing details for more information.brbrMain Level/1st Floor:brElegant family room with wood-burning fireplace and a formal 8-person dining tablebrFully Stocked New Kitchen, Stainless Steel Appliances, Breakfast bar, 6-seater Dining Table and Gas FireplacebrMaster Suite: Queen Bed and ensuite bathroombrLaundry room with washer and dryerbrbr2nd Floor:brMaster bedroom: 4-post king bed with full bath and walk-in closetbr3rd Bedroom: Two twin bedsbr4th Bedroom: Twin-over-full bunk bed and a twin bed with trundle brFull BathroombrbrLower level:brEntertainment/Home theater with 70-inch TVbrBar, 40-bottle wine cooler and refrigeratorbrKids' game room with 65-inch TVbrQueen-size sofa bedbrFoosball tablebrPing Pong tablebrFull BathroombrbrOutdoor Living: brSprawling DeckbrOutdoor 8-seater dining table with UmbrellabrWeber Gas GrillbrRattan Furniture seatingbrGas FirepitbrSecluded Heated Swimming Pool - The pool is set against the lush backdrop of the conservation landbrPool basketball hoopbrPool Floats and TubesbrPool Lounge Chairs with UmbrellabrOutdoor ShowerbrFenced yard (back)brBasketball HoopbrbrGeneral: brWifi to access the internetbrSmart TVs (access to Netflix, Amazon Prime, etc.)brCable TVbrBoard GamesbrLinens and Towels includedbrBorrow Beach Chairs (8) and Beach Umbrella for usebrBorrow Beach sand toys for usebrCentral Cooling and HeatingbrParking: Driveway for 4 vehiclesbrbrPlease note that for security purposes, this property has security cameras that record or transmit video, images, or audio. Camera 1 is over the leading garage door, Camera 2 is over the front door, and Camera 3 is inside the garage.
Bed 4

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Bath 4

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Exceptional(83)

$1663.3

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Private Vacation Home

Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More

Chatham, Massachusetts, United States

This lovely home is the perfect getaway for families or a group of friends looking for a home filled with entertainment that is close to downtown Chatham, beaches, and much more. This cozy home has an open concept living area, kitchen/dining room space, a large outdoor space equipped with a massive deck, yard, grill, and fire pit, as well as a fully furnished basement with a game room.brbr2 Min Drive to Downtown Chathambr6 Min Drive to Lighthouse Beach brbrExperience Chatham with us & Learn More Below! brbrKEY FEATURES:br☀ Sleeps 8; 4 bedrooms, 2 king, 1 queen, 2 twin br☀ 3.5 Bathrooms; 3 full (2 full baths have combined tub + shower) + half bathroom br☀ Top of the line mattresses, 100% beautiful cotton linens and fluffy blankets br☀ Open concept living room, kitchen, and dining area with cathedral ceilings and fireplace br☀ Dining room table seating for 6 guests, with 4 bar stool seats at the kitchen counterbr☀ Modern amenities and well-equipped kitchen with wine cooler br☀ Large, brand new deck inclusive of a dining table with seating for 8 guests + umbrella, couch + seating area, 2 reclining lounge chairs, and Weber gill br☀ Yard with a fire pit and seating br☀ Finished Basement with Pool Table, Foosball Table, and Board gamesbr☀ Bikes, Helmets, Beach Chairs, Beach toys, Beach balls, Cooler, Boogie Boards, Cornhole, Bocce, Beach Towels, and Basketball Hoop br☀ Walking or a short dive to many shops, restaurants, and markets br☀ Newly renovated with comfortable and stylish furniture throughout br☀ At the end of a quiet road, nestled into conservation land, surrounded by hydrangeas br☀ Outdoor shower br☀ 4 Smart TVsbr☀ Clean as can be! We pride ourselves on the cleanliness of our home br☀ Bonus Room! Above the garage 1 bedroom + full bath for an additional charge (Available - late May-early Nov)brbrHere Are A Few Kind Words From Our Past Guests:brbr“This is a beautiful home. The beds are all very comfortable; the whole house very clean and the property beautiful and quiet. My son loved the pool table. I enjoyed the peaceful backyard and the sound of birds in the morning.” - Christine S.brbr“House was fantastic and just as described. We could walk to many places but had our private paradise in the backyard. Communication with the host was excellent. Highly recommend the home.” - Michael J. brbr“Everything about this well appointed house makes it an ideal Cape Cod experience for quiet, clean, and spacious days right near beaches and shops. We are already booked for next summer.” - Tara S. brbr“This was an amazing property and so well equipped and centrally located. Lois has thought of everything and the place is super clean with tons of beach stuff, towels, supplies, etc. We loved the property and it was perfect for our kids and the location to town was awesome. Would definitely come back!” - Angela S. brbr☆☆ BEDROOMS ☆☆brbrThis gorgeous home accommodates 8 guests in 4 bedrooms. brbrOn the main level of the home, there is one master bedroom, fitted with a king-size bed and a private full bathroom. Also on the main floor is a bedroom fitted with a queen-size bed, across from a half-bathroom. brbrThe upper level accommodates another four guests. One master bedroom is fitted with a king-size bed and ensuite, the other bedroom has two twin beds. brbr☆☆ BATHROOMS ☆☆brbrThere are three full bathrooms and one-half bathroom in this home, each of them stocked with all the essentials you need for the duration of your stay including shampoo, conditioner, soap, two blow dryers, and two hair straighteners. brbrThe main level of the home has a full bathroom in the master bedroom, and a half bathroom close to the kitchen and second bedroom on the first floor. The second level of the home has a full bathroom with a large combination shower and tub. There are two doors to the bathroom - one off of the master bedroom, and another one off of the hallway for easy access from both bedrooms. Worry about nothing with these thoughtfully stocked bathrooms that provide everything you need and more. brbrThe finished basement has a full travertine bathroom. There is also an outdoor shower. brbr☆☆ KITCHEN & LOUNGE ☆☆brbrLiving Room: The living room is cozy with a couch two large chairs around a fire place and smart TV. brbrKitchen: The bright and airy kitchen is fully stocked with all the appliances, cookware, and utensils you need to feel at home including a coffee machine + coffee. There are also 4 counter stools. brbrDining area: The dining area seats 6 guests surrounded by stunning nautical decor. There are slider doors next to the dining area that go out to the deck. brbrFinished basement: Couch, TV, pool table, foosball table, board games, puzzles, beautiful travertine bathroom with shower, and walk-out sliding door to the back yard and outdoor shower. Perfect place to unwind and have some fun! Please know there is no heat in the basement. brbrThere is a washer + dryer, equipped with laundry detergent in the hallway close to the first-floor bedrooms. brbrOriginal paintings of Chatham throughout the house by local Chatham Artist, Lois Castellana. brbr☆☆ OUTSIDE SPACE ☆☆brbrThis home is at the end of a quiet street, nestled in conservation land. There is a long driveway leading to the house with a basketball hoop at the top. The backyard has a large mahogany deck equipped with a dining room table with seating for 8 guests + umbrella, couch/seating area, 2 reclining lounge chairs, and Weber gill. Below the deck is a large yard perfect for lawn games, with a fire pit and seating. There are sliding doors leading to the deck off of the kitchen, and also off of the living area in the basement making it accessible to go in and out. brbr☆☆ NEED AN EXTRA BEDROOM ☆☆brbrFor an additional rental fee, there is a room above the detached garage with king king-size bed, sitting area with TV, window A/C unit, and bathroom. Please inquire if interested. Please know this space is only offered to whomever is renting the house.brbrPricing: br- June-Sept: $295/night br- Oct-May: $250/night brbrPlus $200 cleaning brbrAvailability: br- April through early November brbr☆☆ HOUSE RULES ☆☆brbr- No events or parties.br- No more than 8 guests max allowed at the home or 10 if you also book the apartment above the garage.br- No pets.br- No smoking.br- Quiet hours: 10pm-8ambr- No food or drink other than water in the living areas or bedrooms.br- Must be 25+ years old to book.br- This is a private family home, please be respectful.brbr☆☆ WHEN REQUESTING TO BOOK ☆☆brbrPlease share a bit about yourself - what brings you to Chatham, who you are traveling with, and how many people will be staying at the property.brbr☆☆ A NOTE FROM US ☆☆brbrOur family and friends have always enjoyed the comforts of this family home, we know you will too! There is a lot of space to relax and enjoy your Cape Cod vacation at Chatham Breeze. You can enjoy the sweet sound of birds while sipping morning coffee on the deck, or cook your favorite fish on the grill with family & friends, relax in the sun with a good book, or watch the kids play basketball, foosball or the many other activities all over the property, everyone has a piece of vacation heaven at Chatham Breeze.brbr★★★ Book Today & Let Us Take Care Of You In Chatham! ★★★
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Bath 3

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Sleep 8

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Exceptional(40)

$672.4

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Private Vacation Home

In Town Newly Renovated Cape

Chatham, Massachusetts, United States

Location, Location, Location – New to the rental market, this fully renovated centrally located cape home checks all the boxes. Within minutes you can walk to some of Chatham's top attractions including Downtown, Chatham Bars Inn, Oyster Pond, Chatham A's baseball games and the Fish Pier. brbrThis well-appointed home features a new chef’s kitchen with a 20' vaulted ceiling open to sunroom/seating area. Sliding doors take guests from the sunroom to a patio with outdoor seating or you may enjoy your meal in a separate dining room just off the kitchen. Kitchen features stainless steel appliances, white cabinets, white quartz countertops and a large island with seating. Also downstairs is a new laundry room and full bath. Rounding out the first floor is a comfortable living room, a perfect place to gather with family and friends and enjoy the Red Sox games on the new 55 inch flat screen TV. brbrUpstairs is three bedrooms and one full bath. All have been repainted, and the wide pine floors have been restored to their original beauty. The bedrooms have new furniture and new bedding. Two bedrooms with queen beds and the third bedroom, the “kid’s room”, features bunk beds and a twin bed. brbrAfter a day at the beach, rinse off the sand in the new outdoor shower while your kids enjoy playing whiffle ball in the large, private side yard. brbrEnjoy the comforts of your own home in this well-equipped Chatham rental. There is no need to pack up two cars to go on a family vacation anymore. This inviting home is stocked with new linens, towels, beach towels and blankets, beach toys, back pack beach chairs, adult bikes, Double & Single BOB Jogging Strollers, McLaren stroller, red wagon, Graco Pack ‘n Play, high chair, board games and many other items to make you feel right at home. brbrWhether you are a family looking to enjoy the sand and surf or a couple looking to explore all that Chatham has to offer, this newly renovated home is the perfect place for your next vacation. brbrbrAmenities: br-New amenities include Central Air Conditioning in entire house, Outdoor Shower, Weber Gas Grill, Sonos, 55 inch Samsung Cable TV, and much more.brbrbrLess than 10 minute walk to the following landmarks/attractions:br-Downtown Shopping/Restaurants br-Chatham Bars Inn via a walking path at end of streetbr-Oyster Pondbr-Chatham Anglers Games/Children's Playgroundbr-Chatham Fish Pier brbrbrbr
Bed 3

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Bath 2

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Sleep 8

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Exceptional(1)

$572.33

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Private Vacation Home

Chatham Shenanigans, Chatham Shenanigans

Chatham, Massachusetts, United States

Experience the beauty of Cape Cod at Chatham Shenanigans. This beautiful, well-appointed, bright home is centrally located to all that Chatham has to offer. It’s the ideal spot for discerning guests looking to be close to the hubbub of town but in a serene, private, and quiet setting. brbr~Just a 5 min drive or mile walk to enjoy downtown Main Street restaurants, shops, and Cape-league baseball br~Less than 5 min drive to Hardings Beachbr~4 great restaurants within walking distancebrbrThe spacebrKEY FEATURES:br☀ 3 luxurious bedrooms; 1 king, 1 queen, 2 twinsbr☀ Private den/office with additional queen pull out sleepingbr☀ 2 full bathrooms + 1 half bathbr☀ Full kitchen stocked with all your cooking needsbr☀ Cozy living room w/ indoor fireplace + flat-screen TVbr☀ Lower-level living/game room w/ an additional TV, ping pong table + card game tablebr☀ Outdoor living area w/ a solo stovebr☀ Full washer + dryerbr☀ Quiet and private location only minutes from all that Chatham has to offerbr☀ Free parkingbrbr☆☆ BEDROOMS + BATHROOMS ☆☆brEach of the three bedrooms is designed with guest comfort in mind. brbrThe primary bedroom with king-sized bed and en-suite is on the main level. The second floor boasts two additional bedrooms - one queen-sized bed and another with two twin-sized beds perfect for both kiddos and adults!brbrThe main level has one half-bath off the garage entry. There is a full-bath with walk-in shower and double sinks ensuite to the primary bedroom on the main floor. The second full bathroom is on the second floor and includes a shower/tub and is shared with the bedrooms on this level. brNOTE: As is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property.br☆☆ KITCHEN & DINING ☆☆brThe open-concept main level of the home boasts soaring ceilings and views of the private backyard. The kitchen and dining area offer plenty of room to comfortably host family dinners and are outfitted with all the cookware, dishes, utensils, dishwasher pods, and appliances you will need to cook delicious meals. The farmhouse dining table can seat up to eight.brbr☆☆ LIVING SPACES ☆☆brThere are three separate indoor living spaces around the home: one first floor living area, one comfortable den/office on the main floor, and one in the basement lower level. Each of the bedrooms also has a small seating nook if you’re looking for a little more privacy from the rest of the group.brbrThe main living area boasts floor-to-ceiling windows, which allow you to enjoy the secluded and private views of the backyard from the comfort of the sofa or plush chair. There’s also a large flat-screen Smart TV for movie night.brbrThe den/office is a relaxing space where you can fully immerse yourself into the pages of your next read or work from anywhere at the desk with beautiful views of the conservation land across the street.brbrThe lower-level is a bright and open space with a big-screen TV, a quality ping pong table, and a game table with a small collection of fun games for the family.brbr☆☆ OUTSIDE SPACE ☆☆brWhile there are plenty of outdoor activities nearby, the house also provides its own outdoor sanctuary for guests to enjoy. We invite you to enjoy a competitive game of corn hole, relax on our private patio or settle in for a quiet evening by the solo stove. There are plenty of seating areas for guests to sip morning coffee in or enjoy a happy hour drink as the sun goes down. String lights provide ambient lighting and there is a large outdoor dining table for al fresco meals.brbr☆☆ ADDITIONAL INFO ☆☆brThis home also offers first-floor laundry and a 2 car garage to store all your beach gear. brbrWe provide many household staples to get you started – Paper Towels, Toilet Paper, Soap, Laundry Detergent, etc. As is customary on Cape Cod, linens and towels are not provided but may be provided to guests through a third party. This is not included in the rental price. Please inquire about pricing and referrals. brbrGuest accessbrGuest have private access to the full property with the exception of the storage room in the basement. There is free parking available in the driveway.brbrImportant NotesbrNo pets allowed.brNo smoking or parties allowed on the property.brPrimary renter must be at least 25 years old to book. A valid photo ID is required prior to check-in.brAs is common on Cape Cod, Guests are responsible for providing their own linens, including sheets and towels, at this property. Pillows, blankets and covers are provided. Guests can bring their own or we refer to Chatham Concierge for linen services where you can rent from their online store. They can deliver linens to the property on your arrival date and pick them up on your departure date. The cost for linen rentals varies depending on your needs and planned occupancy.brA rental contract must be agreed to during the booking process. The Guest is responsible to read and understand the rental rules prior to booking. By clicking Request to book the Guest is accepting all of the terms and conditions.brThis home is on a septic system so occupancy is strictly enforced to avoid a septic backup of sewage in to the house. Your max occupancy during your booking is what you submit in your booking. Additional guests must be approved.brCheck-out time is strict, and if our cleaners arrive while you're still at the house, we may incur extra charges, which will be passed on to our guests.brWe are not responsible for any injuries, illnesses, or accidents that may occur during your stay, nor for the loss of personal belongings or valuables.brA Trust + Safety Fee is applied per night in lieu of a security deposit.br ★☆ Book Now & Let Us Take Care Of You at Chatham Shenanigans! ☆★br Follow & tag us on Instagram: @pleasantchathamcapes
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Exceptional(12)

$1104.16

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Private Vacation Home

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Chatham, Massachusetts, United States

This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachusetts. Fresh and new, the Townhome also includes access to a swimming pool and tennis courts. brbrTownhome 31 features a well-appointed master bedroom with king bed. Second bedroom has 2 full beds. An amazing loft has an additional two twin beds, plus a beautiful den has a Queen Sleeper sofa. Ideal for two or four people, and can accommodate up to eight people when using lofts. Also boasts a fully-equipped kitchen and water views. Beautifully decorated with charming interior decor.brbrEach has picturesque views of Oyster Pond and plenty of open space. Townhome 31 may be rented with Townhome 32 for approximately 4,250 SF of living area (contact Owner for more details).brbrOyster Pond Condominium Complex includes free tennis court, swimming pool, shuffle board, acres of lawn for kite flying, playing catch, and family fun. Wide range of excellent nearby restaurants from super casual on up. Restaurant listings available as are brochures on activities for adults and kids. All summer take your family to the famous Chatham Band Concert, Cape League baseball, and Summer Theatre. Sightseeing, whale watching, seals, cycling, beaches, golf, movies are all nearby. Small kids activities in Chatham also include a huge playground and a train museum, both right near a real fire station. Oyster Pond’s great location is nearby Chatham Main Street’s strolling and shopping.brbrConvenient walk to downtown Chatham location. Close to Atlantic Ocean, Nantucket Sound and Oyster Pond beaches, as well as golf and all the best Cape Cod has to offer.brbrBring your canoe, kayak or Sunfish and use private dock on Oyster Pond providing access to the pond, Oyster River, Stage Harbor, Nantucket Sound, South beach, Monomoy Island and the Atlantic Ocean. Nearby Oyster River Boatyard offers power boat rentals.brbrAmenities include: Heated swimming pool, tennis; shuffleboard, patios, fully appointed kitchens, washer & dryer, gas grill, cable TV, full central air conditioning and heating, wireless internet, and morebrbr See other units we have available: VRBO #3926813 and #4209584 brbrTown of Chatham permit STR-323.
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Exceptional(67)

$621.66

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Condo

Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!

Chatham, Massachusetts, United States

Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end-unit condo is as close to the ocean as you get!brbrThis open floor plan home is steps away from the condo association’s private beach, and offers gorgeous views from almost every room. Imagine sipping your coffee early in the morning, sitting on your own deck to watch the tide come in.brbrClamming and fishing are plentiful and this location has a protected harbor and the fastest access out to Nantucket Sound and the Atlantic. Outermost Harbor Marine Harbor is right next door. Downtown Chatham, with its restaurants and shopping, is just a walk or bike ride away. The nearby Monomoy National Wild Life Refuge offers plentiful birding and opportunities for exploring!brbrThe living room features a sleep sofa and large, flat-screen TV. The two bedrooms (one with a king bed and the other with two twins and a twin pull-out) also offer flat-screen TVs.brbrThe kitchen has a dishwasher and granite countertops. Unit also includes a stacked washer/dryer, central A/C, free wifi, and a basement with ping-pong table. In addition to the private ocean-front deck and an outdoor sitting area for two featuring Adirondack chairs set on a “floor” of crushed shells, there is also a long, covered patio along the side of the building with a gas grill, picnic table and additional seating for 6-8.brbrThis is the Cape Cod lifestyle at its finest!brbrNo smoking and no pets, please! Maximum of two cars may park in the property lot.brbrNOTE: We supply pillows, blankets, mattress protector, toilet paper, paper towels, laundry detergent, dish/hand soap. We DO NOT SUPPLY towels, bed sheets or pillow cases, though bed sheets and pillow cases can be provided upon request (nominal fee) or can be ordered from Cape Cod Linens or Furies Online. br brDuring peak dates (June through mid September) a minimum one-week rental is required. Three-night rentals may be available at other times of year.
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Exceptional(82)

$389.13

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Cottage

Secluded Chatham Cottage Near Hardings Beach

Chatham, Massachusetts, United States

Welcome to our totally updated 'old Cape' style cottage. Guests have access to a wide variety of indoor, outdoor, and beach amenities. brbrThe Space:brDesigned for today's living while retaining its 'old Cape' charm, the sunny, open spaces and updated amenities will allow you to effortlessly enjoy your vacation. Available year-round whether to relax at the beach, to celebrate holidays, or just as an off-season get away.brbrThe comfortable living space encourages everyone to gather for a spirited game of Chathamopoly or to snuggle in for a night at the movies. Here you’ll find a 42” TV, wireless internet, books, and games.brbrThe gourmet kitchen features a large island and is outfitted with stainless steel appliances, dishwasher, microwave, and professional cookware. brbrEach bedroom is uniquely decorated. There is an elegant couples retreat with a queen bed. A bright room with two twin beds that celebrates the beach cottage theme. Finally, feel like you're sleeping aboard a sailing vessel with the nautical themed twin over full bunk bed.brbrKeep the beach clutter and laundry contained in the back 'sandroom' with a full-size washer/dryer and easy access to the outdoor shower that has both hot and cold running water.brbrCentral heating and air conditioning keeps the cottage comfortable regardless of the weather.brbrIncluded in the cost is a linen service providing fresh bed linens and bath towels. Other essentials like comforters/blankets, pillows, paper goods, and cleaning products are also provided, but remember to bring your own beach towels.brbrOutside:brOutdoors there is a large lawn for games, a sunny patio with ample seating and both a gas and charcoal grill, a covered front porch, and off-street parking. For the beach there are several chairs, a beach umbrella, and umbrella anchor in the basement.brbrThe large 1/2 acre lot is wooded on 3 sides, offering a fantastic sense of privacy, but the yard stays sunny and is great place for games or a round of tag. brbrA large bluestone patio right off the kitchen catches the warm afternoon sun and offers ample seating for entertaining. Fix a drink and unwind while cooking the catch of the day on either the gas or charcoal grill.brbrFor the security of our guests and the safety of our home, there is a single exterior security camera strategically positioned to monitor the driveway and front walk only. Guest privacy is maintained on the rest of the property. There are no interior cameras. brbrThe Neighborhood:brThe cottage is tucked away on a quiet, private street, but remains close to everything wonderful that Chatham and the Cape have to offer!brbrOne of the best beaches on the Sound, Hardings Beach, is less than 1 mile away. There is sidewalk access from our cottage to the beach for a safe walk or bike ride. We are also just a short drive to the other beaches on Nantucket Sound, Oyster Pond, or School House Pond, which is one of the nicest fresh water ponds in the area.brbrFor bikers it is easy to pick up the Old Colony Rail trail to Harwich where it connects to the Cape Cod rail trail that runs 22 miles from Dennis to Wellfleet.brbrThe charming Main Street of Chatham Village is less than 2 miles east on Rte 28. Harwichport is a few miles west. Both favorite spots for a day of shopping or a night out.brbrHouse Rules:brThe first rule is always to relax and have fun! To continue to keep the cottage enjoyable for everyone we also ask that you:br- Do not smokebr- Do not bring your pets (sorry, but we have allergies)br- Be respectful of our neighbors as several live here full timebr- Leave the cottage clean and organized when you depart; Dispose of all remaining food and place garbage in the outside bin; Load, run and empty the dishwasher; Strip the bed linens, gather used bath towels, and place on the floor for the linen servicebr- Report any damages or concerns to the Owners so that we may address the issues.
Bed 3

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Sleep 6

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Exceptional(18)

$449.63

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Cottage

Charming Cape Cottage in Chatham, 2 Min From Beach

Chatham, Massachusetts, United States

Forest Sands cottage is comfortably decorated in Classic Cape style, a 2 minute walk from Forest Beach, and 10 minute spectacular walk through the dunes to Cockle Cove. Two bedrooms, two baths (one an outdoor shower), with pull-out sofa in family room (sleeps six). The quaint interior has Large flatscreen TV featuring access to main Streaming services, Media players, Hi-speed Internet and central Air Conditioning. Washer/drier, gas grill, and bicycles are in the garage. Easy access (1/8 mile) to the Old Colony Rail Trail between Chatham and Dennis, which joins the Cape Cod Rail trail to Wellfleet. A 5-minute drive to Red River Beach and 10 minutes to charming shops and restaurants in Chatham Town Center, which has just won a spot on the Yankee Magazine “25 BEST NEW ENGLAND TOWNS” list for 2026! br Other local features include restaurants and theaters such as The Dennis Playhouse, Cape Melody Tent, Ohio State Players, and the Harwich Junior Theater. Visit the Chatham Airport for charter rides, The Chatham Train Museum, ice cream shops, the Cape Cod National Sea Shore nature preserve, Whale-watching, Monomoy Island seal cruises, and fast-ferry day cruises to Nantucket. Charter fishing boats operate nearby. Take a stroll through shopping streets of town to Chatham Light.brbrChatham is one of New England's most beautiful locales, and its unique location on the Cape surrounds it with water, harbors, dunes and sandbars on three sides. A fantastic place to visit, on-season or off-season.brbrDURING YOUR STAY:br• We especially request that you limit the number of people present while you are at the house to your immediate group or family only, and that you not invite additional persons to visit the house or grounds, so please, no picnics, bar-b-cues, or parties.br• We are also requesting that you limit the number of vehicles parked in the driveway to no more than 3, and refrain from street parking, especially overnight.brbrBEFORE YOUR DEPARTURE:br• Please strip all beds, and place bed linens and towels in washing machine (in the garage) with detergent, set dial to “regular” cycle/ “hot” water, and pull to run. Please leave second or third loads in the hamper. Thanks!br• Please place all household trash in black garbage bags (provided), and recyclable materials in blue or clear ones (provided). Bags are under the kitchen sink. Gather all together by metal trash can in the garage - we are happy to take it from there. Safe trip home!
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Bath 1

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Sleep 4

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Exceptional(10)

$465.81

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Cottage

Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach

Chatham, Massachusetts, United States

If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and play, and it is set back from the street and other area houses. This is the only cottage in the area, and it's neighbors are multi-million dollar houses. It is clean, modern, in first class condition, and with great amenities. We live here when our children take over the main house that is 200 yards to the rear. Approximately 3/4 of our renters re-book the following year, and some have been coming for 20 years! The age range of guests is from infant to 90+. br Curl up with that book or just close your eyes because you know this house and yard is a perfect getaway.brHardings Beach - the most popular area beach because of its warmer, calmer water, wide clean sand, and a one mile beach walk to the lighthouse. It's a 2 minute walk with the children along a wide pedestrian sidewalk to the beach. Look for the seals, boats heading into Nantucket Sound, wind surfers, fishermen, the famous fish weirs off shore, and lots of shells to find. brPick your Hideaway – put that lawn chair under a shade tree or a secluded, sunny spot.brNeed to borrow some sand or lawn toys We have several to choose from.brBring your bikes and store them in the garden shed. The Cape Cod Bike Trail goes for 22 miles and is only a 4 minute drive up the road.brOutdoor Private Shower - (please, only one person at a time unless you're in a committed relationship!!)br2 Bedrooms – 1 with a new queen and 1 with 2 twin beds with new mattresses.br3 Season Porch - built 2018, 220 sf, wood paneled, 10 sets of windows/screens, separate screen door and inner dutch door, vaulted wood ceiling, dining table with 6 chairs, and separate seating area with wicker furniture and coffee table.brLiving room has a sofa, easy chairs, fireplace (not usable), internet ready TV and DVD, VCR, internet, wifi, and coffee table/floor space for games and toys.brbrThe property also includes a separate, 5 bedroom house that is 200’ further back on the property and is rented during the summer. The larger house is virtually unseen from your house as it is shielded with numerous trees, bushes, and the car parking area. A 2 bedroom cottage is near the larger house; however this is not rented out. One of my children may use it at some point during the summer to help me with the upkeep and maintenance of the the property.br
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Exceptional(53)

$421.12

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Condo

Full Renovation! Amazing Spot with Views!

Chatham, Massachusetts, United States

Summary:brbr16620 - A Step Above: Full Renovation! Amazing Spot with Views!brbrbrbrThe Space:brbrOur completely renovated and newly furnished condo, located directly in the center of town on Main Street in Chatham, is the perfect vacation spot for your next trip to Cape Cod. You will be a short walk away from many great restaurants, including Impudent Oyster, Chatham Squire, Bluefins Sushi & Sake Bar, and Wild Goose Tavern, as well as a variety of local shops, galleries, a movie theater, and plenty of other entertainment options. In addition to offering a central Main Street location, our condo is just a short drive from a number of desirable Chatham beaches; Lighthouse Beach and Oyster Pond Beach are each just a three minute drive away!br brEnter our thoughtfully-decorated second story condo to find a welcoming bright, open, and clean kitchen and living area with modern decor. Some features include new appliances, island seating, a large flat screen TV with sectional couch seating, central A/C, a washer/dryer, deck with gas grill, and two bedrooms on opposite sides of the condo, providing a level of privacy for each guest. Want to go shopping for shoes - just downstairs on the 1st floor of our condo building is the ultra-chic If The Shoe Fits boutique. Grab something new for your evening or beach outings. Such an amazing location with all the amenities you will need, in addition to being dog friendly, makes this vacation rental one that you won’t want to miss out on!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 4br-Single Floor (2nd story walkup)br-Bedroom #1: 1 King Bedbr-Bedroom #2: 1 Full Bedbr-Central A/Cbr-Cable TVbr-WiFibr-Washer/Dryerbr-Deckbr-Gas Grillbr-Located on Main Streetbr-Minutes to the Beachbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0427480550brbrbrbrThe Neighborhood:brbrOceanside
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$4341.83

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Private Vacation Home

Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound

Chatham, Massachusetts, United States

brbr***SPECIAL REDUCED RATE: Last week of June into July (6/26-7/3) Friday to Friday ~ Reduced $5k***brbrbrbrStroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound .brRecently built to suit every vacationer's whim. This truly one-of-a-kind compound will be sure to delight all of your family and guests. The estate sprawls with resort inspired land and hardscapes, pool, and outdoor firepit, nestled alongside the headwaters of Upper Mill Pond & Mitchell River. There are two well appointed dwellings on the property consisting of a 4+ bedroom main house as well as a 2 bedroom guest cottage. Both homes were lovingly designed with exquisite furnishings, modern en-suite baths and kitchens, and attention to every detail and interior refinement. The main floor affords a first floor primary bedroom with en-suite bath. The main floor also affords a laundry, pantry, powder room, and a living/dining great room off of the kitchen. From the main floor guests can overlook the pool deck below from a deck outfitted for outdoor dining and grilling convenience. The second floor features two additional guest bedrooms with vaulted ship-lap ceilings which share a hallway bathroom. The lower level offers a large family/media room with a wet bar, another full bath, exercise room (with bonus murphy king bed) and another ensuite bedroom. The pool deck is surrounded by native stone retaining walls, luxurious seating for lounging, a gas fire pit to extend your evenings, and of course a Cape Cod staple... outdoor shower.brAdjacent to the main house is an adorable two bedroom cottage with a great room a first floor eat-in kitchen and living room. Above yields two well appointed guest rooms each with their own baths and a second floor stackable laundry in the hallway closet. brbrMain House:brBR1 - 1st Flr - King Ensuite BathbrBR2 - 2nd Flr - King Hallway Guest BathbrBR3 - 2nd Flr - 3 Twins and 1 Twin w/ Trundle Hallway Guest BathbrBR4 - Lower Level (walkout) - King Ensuite BathbrBonus Room - Lower Level - King Murphy Bed - Hallway Guest BathbrbrCottage:brBR5 - 2nd Flr - King Ensuite BathbrBR6 - 2nd Flr - 2 Twins w/ Trundles Ensuite BathbrbrBEDS MADE UPON ARRIVALbr$1500 SECURITY DEPOSIT REQUIRED
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Exceptional(20)

$944.21

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Private Vacation Home

Walk to the Beach ~ Chatham rental

Chatham, Massachusetts, United States

WALK TO JACKKNIFE COVE BEACH in Chatham from this charming, clean, and well-kept home. Enjoy s'mores with the kids at our Outdoor wood FIRE PIT. There is room for more than one family and plenty of space to spread out. There is Wi-Fi, Central Air. There are plenty of board games and puzzles for families to play. Fully equipped kitchen with stainless steel appliances. The unfinished but clean basement has ping-pong table, foosball table, air hockey and dart board. Enjoy outdoor living on a large deck with gas fire pit, hammock and Adirondack chairs to relax in. There is an outdoor enclosed shower with hot/cold water to rinse off when you come home from a day at the beach. This home is nestled in a quiet, peaceful neighborhood and only a quick stroll to Pleasant Bay, where there is a perfect beach for kids and adults.brbrWe look forward to welcoming you, your family and friends into our home.brbrTHE WHALE HOUSE IS EQUIPPED WITH EVERYTHING A FAMILY DESIRES FOR A GREAT VACATION!brbrAt Pleasant Bay, which is just a short walk from the house, you will find both a comfortable beach to relax on and a sheltered cove for children and adults. Jackknife Cove has nice views of the tide and you can swim and search for crabs in the warm shallow water.brbrWeekly beach stickers for Hardings, Ridgevale, and Cockle Cove Beaches, and parking along Bridge Street are available at the kiosk in the beach parking lots.brThe price changes from year to year. One pass is good for all three Chatham beaches and/or for the parking along Bridge Street for Lighthouse Beach. You can also pay for one day parking.br
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Exceptional(45)

$314.74

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Cottage

Quaint Two Bedroom Lakeside Cottage #18 with Screened-in Porch in Chatham

Chatham, Massachusetts, United States

Must bring your own linens. New kitchen, granite counter tops, new hardwood floors, new drywall and paint. Cathedral ceilings in open kitchen/living room space. This is a charming 2 bedroom cottage in private community nestled among the pine trees on White Pond. Perfect for small families or a couple who desires extra space. It will comfortably sleep 5. Master bedroom offers a queen sized bed and second bedroom is equipped with a double bed with a twin mattress. Screened-in porch is perfect for quiet evenings in or relaxing mornings drinking coffee while listening to song birds. Swim at the private beach in a fresh water lake or take a short 5 minute drive to various ocean beaches. Chatham's downtown is only 2 miles away and is filled with wonderful boutique shops and fine restaurants that rival Nantucket's best. This cottage offers an exclusive getaway without the expense of Chatham's many high-end resorts. Bring your bikes, kayaks or canoe to take advantage of the pond and walking trails that provide an abundance of nature's many gifts. Friday night band concerts or a trip to North beach to explore the harbor seals are a must for the children. NO PET POLICY, violation will result in loss of full deposit. Linens are NOT INCLUDED, you will need to bring your own. Internet only, no cable TV. Must bring your own linens (sheets and towels).
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Exceptional(9)

$602.17

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Private Vacation Home

On the Chatham Loop - 1 Min to the Beach!

Chatham, Massachusetts, United States

Summary:brbr16619 - Chatham Cruiser: On the Chatham Loop - 1 Min to the Beach!brbrbrbrThe Space:brbrChatham Cruiser is the perfect mix of modern comfort and historic charm, offering a classic Cape Cod summer experience. brbrStart your day in the beautiful kitchen, and once breakfast is ready, sit down in the sun-soaked breakfast nook for the most important meal of the day. Relax in the bright living room before heading on a nice stroll through the gorgeous Chatham neighborhood to get to Oyster Pond Beach - the perfect place to take the kids for the day. Main Street is also just down the road, where you will find plenty of options for dining, shopping, and entertainment. br brReturn home to the patio in the back, under the shade of the Japanese cherry tree. Serve up BBQ and evening cocktails, with the large, fenced-in yard being a great space to play lawn games, entertain, and regroup to go out and enjoy some evening fun at the many beaches or restaurants close by. Retire for the evening to one of the five bedrooms, all with air conditioning to beat the summer heat. The primary bedroom has a queen bed, with another queen bed on the second floor, twin beds in bedrooms 3 and 4, and two twin beds in the final, fifth bedroom. brbrOther amenities include an outdoor shower, propane grill, washer/dryer, multiple TVs with cable, and numerous indoor and outdoor dining options. Staying at Chatham Cruiser, you will feel the stories this home has experienced, and can excitedly add to the rich history of this Cape gem. brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 8br-2 FloorsbrBedroomsbr-Total 5br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Twin Bedbr-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Twin Bedbr-2nd Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 2br-1st Floor: Full Bathroom w/ Shower/Tub combobr-2nd Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Fully Equipped Eat-In Kitchenbr-4 Mini-Split A/C Units + 2 Window A/C Unitsbr-Smart Lockbr-TVbr-WiFibr-Washer/Dryer (1st floor)br-Patio w/ Outdoor Diningbr-Propane Grillbr-Outdoor Showerbr-Private Fenced-In Yardbr-NO Pets (fines remitted)br-Located on the Chatham Loopbr-Minutes to Oyster Pond Beach & Main Streetbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0409890550brbrbrbrThe Neighborhood:brbrOceanside
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Exceptional(111)

$338.42

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Apartment

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham, Massachusetts, United States

** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the house now has a new foundation, upgraded systems and a modified floor plan. We've worked had to maintain the character and charm of the antique home, while bringing it up to modern standards. We can't wait for renters to experience the results for the 2025 summer season and beyond! brbrThe Lena Coleman apartment is the least-changed of the four apartments at Ship's Light. The layout remains the same, with a fully-equipped open kitchen/dining/living room area, cozy bedroom with comfortable queen-sized bed and a beautifully-tiled bathroom with new fixtures. It boasts a lovely porch deck, from which you can enjoy your morning coffee or a glass of wine while watching the sunset. It also has newly-installed, solar-powered air conditioning and heating throughout the apartment. The house has two Level 2 EV ChargePoint chargers for use by renters.brbrShip’s Light has looked down Cross Street to Chatham Village Center for almost 200 years. Built and occupied by some of Chatham’s most eminent residents since 1828, it was converted to four housekeeping apartments for summer visitors circa 1945. Lovingly restored by long-time current owners, this gracious antique home offers modern comfort and convenience with the character and charm of a bygone era. brbrNamed for my grandmother, the “Lena Coleman” apartment is a three-room, one bedroom gem. Airy and light, the eat-in kitchen boasts a bay window, with a round oak table and chairs and stained glass chandelier; the inviting living room has built in cabinets and a cozy window seat, two comfortable chairs and a smart-TV. Wi-Fi is available throughout the house. Perfect for a couple, the bedroom has a comfortable queen bed and a natural bead-board ceiling with exposed beams. The bath is beautifully tiled with a marble sink and sky light. Enjoy your morning coffee on the private roof deck with your loved one or watch the sunset while sipping a glass of wine. The charm of the apartment is further enhanced by the warm glow of beautifully refinished, hand-laid, wide pine, antique floors. brbrCentrally located within a short walking distance of excellent Chatham dining, shopping and band concerts, the house is three blocks from the town salt water beach on Oyster Pond, and one mile from Coast Guard Beach, a great stretch of Atlantic Ocean and dunes. Many individuals, couples and extended families consider Ship’s Light their vacation home. We invite you to join them in making your vacation something special.brbrThe Lena Coleman apartment at Ship’s Light is available for stays of 3+ nights during the summer and shoulder seasons and stays of 2+ nights during the off-season. Other units with unique features are also available and the whole house can be rented as a 5-bedroom home for family gatherings.
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$1629.4

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Private Vacation Home

Barefoot Bungalow: 330-C Exquisite Chatham Home, Easy Access to Town, Bike Trail

Chatham, Massachusetts, United States

This property is professionally managed by Pretty Picky PropertiesbrbrExquisite Chatham Home, Easy Access to Town, Bike TrailbrbrSleeps 10br4 Bedrooms plus flex bonus room, 3.5 BathroomsbrRents Friday to Friday during peak seasonbrLinens Included. Beds made.brPets consideredbrbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrLooking for a luxurious way to experience Chatham Look no further! New to the rental market, this 4 bedroom 3 and a half bath home is ideally set up to welcome groups of up to 10. Built in 2012, this modern home has all the creature comforts you'd expect from a luxury level home. The open floor plan features a fully equipped chef's kitchen that is open to the dining room and the vaulted living room that is flooded with natural light from the sky lights. There is a screened porch off the back that leads out in a beautiful new pool area! The heated salt water pool will have a gorgeous patio area with ample seating and lounging area. There will also be a large 6-person hot tub in the pool area. brbrBack inside, you'll find the spacious primary bedroom with a King bed and an adjoining gorgeous private bathroom with a dual vanity and tile and glass step-in shower. Finally, there is a small room with a twin bed to round out the main level. Upstairs you have a classic Cape set up with a full bathroom at the top of the stairs and a bedroom on either side. The first bedroom has a King bed and the other has three twin beds. brbrBut wait, there's more! The fully finished lower level has a TV lounge, a wet bar and a table for games or cards. There is another guest room with office space and one additional room down here for flex sleeping space with queen beds in each. There is a full bath in the lower level as well.brbrThe house is under a mile from Chatham Village for shopping, dining, and browsing. You're even closer to the Chatham Angler's baseball field for Cape League action. Want to explore by bike There is access to the bike trail less than 1000 feet from the house. Pets are considered so the whole family can enjoy some time in Chatham! 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 Cape Cod.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 $ 245.00br 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 Cape Cod. brbrIt's your vacation. Get Picky! ® brbrTown of Chatham Registration #1095
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