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From $228 per night (USD)
VRBO
Fully Updated Home w/ Great Outdoor Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16648 - Quail Trail: Fully Updated Home w/ Great Outdoor Space! The Space: This beautifully updated house in S ...
From $228 per night (USD)
VRBO
From $223 per night (USD)
Expedia
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cottage is an affordable Chatham getaway destination for a couple or small family who want to experience Cape Cod. ...
From $223 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Contemporary four bedroom home just .5 miles to Inman Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Newer contemporary cape, meticulously maintained inside and out. Perfectly located on quiet cul-de-sac, just an easy .5 ...
From $439 per night (USD)
VRBO
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Expedia
Oceanfront five bedroom home with access to shared/private beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Say hello to your dream Cape Cod vacation in our beautiful oceanfront home! Located in Dennisport, this home is perfectl ...
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Expedia
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VRBO
Three bedroom home with central air conditioning
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Sparkling clean and newly remodeled ranch with central air conditioning and hardwood floors. Large, updated eat-in kitc ...
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VRBO
From $310 per night (USD)
Expedia
Two bedroom home just 2/10's mile to Sea Street Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Well kept, two bedroom home with sleeping for four. Located only 2/10’s of a mile to Sea Street Beach in Dennis Port! Th ...
From $310 per night (USD)
Expedia
From $821 per night (USD)
VRBO
Water Views in Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Cancellation policy at end of property description.* Charming, perfect location and every amenity you could want! Th ...
From $821 per night (USD)
VRBO
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Expedia
Fully renovated 4 bedroom home located less than 500 feet to Sea Street Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Pristine condition! Beautifully decorated, fully renovated four bedroom home with central air. Located less than 500 fee ...
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Expedia
From $204 per night (USD)
VRBO
Immaculately clean 2 bedroom duplex less than .3 miles to Sea Street Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immaculately clean, charming duplex unit completely renovated! Only .3 miles to Sea St beach. Quick walk to local hot sp ...
From $204 per night (USD)
VRBO
From $299 per night (USD)
Expedia
1 bedroom cottage with ac, steps to the beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perfect getaway for up to 2 people! Talk about location! This cozy 1 bedroom cottage is one house away from Sea Street B ...
From $299 per night (USD)
Expedia
From $575 per night (USD)
VRBO
1 Mi to Beach: Home w/ Fire Pit & BBQ in Cape Cod!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2,688 Sq Ft | Dog Friendly w/ Fee | Wet Bar | Expansive Yard Nestled in the heart of South Chatham, this 3-bed, 2.5-bat ...
From $575 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Perfect Locations to beach and bars and restaurants! All walking distance! Private Studio apartment partly renovated! St ...
From $564 per night (USD)
Expedia
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VRBO
Three bedroom cape with water views-Only .2 miles to Seaview Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Lovely, spacious contemporary Cape with water views. Home is situated on a quiet lane just .2 mile to Seaview beach. Th ...
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VRBO
From $281 per night (USD)
Expedia
Lovely 2 bedroom cottage less than 500 ft to Sea Street Beach
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
Cozy Cape Cod Comfort. This lovely 2 bedroom, bath and a half cottage located in the heart of Dennisport. The open conce ...
From $281 per night (USD)
Expedia
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VRBO
Four bedroom home less than 200 ft to shared/private beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
A shared private beach is just 200 ft, with no streets to cross, from this 4 bedroom 2 level home. Window A/C units in a ...
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VRBO
From $211 per night (USD)
Expedia
Adorable cottage on a dead end dirt lane just 200 yards from Sea Street beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming cottage on a dead end dirt lane, located just 200 yards from Sea Street Beach. Cutely decorated with beachy dec ...
From $211 per night (USD)
Expedia
From $438 per night (USD)
VRBO
This spacious 3 bedroom home offers central air and plenty of living space!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This spacious 3 bedroom home offers central air and plenty of living space! Bring your Bocce and Croquet sets and take ...
From $438 per night (USD)
VRBO
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Expedia
Quintessential 4 Bedroom Cottage near Pond and Bike Path
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This lovely Cape has everything you need to settle in and start relaxing. Fully supplied kitchen, 4 bedrooms with linen ...
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Expedia
From $332 per night (USD)
VRBO
Sea Shell Motel - Room 25
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $332 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Sea Shell Motel - Room 28
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $251 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Sea Shell Motel - Room 11
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $188 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Sea Shell Motel - Room 32
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $341 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Three bedroom located 1 mile from Sea Street Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This three bedroom affordable home is located a mere mile from Sea Street beach in Dennisport. Eat in kitchen and a ple ...
From $284 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Sea Shell Motel - Room 23
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $315 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Sea Shell Motel - Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $254 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Sea Shell Motel - Room 24
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $324 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Sea Shell Motel - Room 26
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $214 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Sea Shell Motel - Room 12
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $203 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Sea Shell Motel - Room 22
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $485 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Sea Shell Motel - Room 27
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $205 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Sea Shell Motel - Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $254 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Sea Shell Motel - Room 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $251 per night (USD)
Expedia
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VRBO
Cape Cod Cottage on the Beach at Nantucket Sound
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
JUST AVAILABLE: Relax and beach with your family in this charming, 2BR cottage in Chase's Ocean Grove, a family-friendl ...
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VRBO
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Expedia
Breakers 2BR Cape Cod Condo on Resort w/all resort amenities
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Situated on the beautiful sandy beaches of Nantucket Sound is The Breakers Resort, one of two Bluegreen Vacations resort ...
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Expedia
From $356 per night (USD)
VRBO
15 Minute Walk to Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16632 - Casa Al Mare: 15 Minute Walk to Pleasant Street Beach! The Space: Your perfect seaside getaway starts ...
From $356 per night (USD)
VRBO
From $471 per night (USD)
Expedia
Amazing Location! Lakefront Waterside Deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16629 - Dock Holiday: Amazing Location! Lakefront Waterside Deck The Space: Get ready for a week of rafting, c ...
From $471 per night (USD)
Expedia
From $353 per night (USD)
VRBO
56 Chase Ave - SD150
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Breakers Oceanview A delightful Oceanside resort offering over 500 feet of beautiful private beach in Dennisport. Conven ...
From $353 per night (USD)
VRBO
From $660 per night (USD)
VRBO
Stylishly Furnished Home- Access to Pleasant Street Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Cancellation policy at end of property description.* Sophisticatedly furnished and well maintained 3BR/2BA with a bon ...
From $660 per night (USD)
VRBO
From $402 per night (USD)
VRBO
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air ...
From $402 per night (USD)
VRBO
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Expedia
Oceanfront 5 bedroom home sleeping 10-Stunning views
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy your vacation in this well maintained 2000 sq. ft 5 bedroom home with central air conditioning. The first floor ...
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Expedia
From $585 per night (USD)
VRBO
Cozy Cockle Cove Retreat!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this adorable coastal cottage, perfectly nestled just half a mile from Cockle Cove Beach in Chatham. Offering ...
From $585 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Private Beach , in room Hot Tub, BBQ, HEATED POOL, INDOOR POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
free parking space at the resort indoor heated and outdoor heated pool indoor heated pool available next building calle ...
From $315 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Quintessential Chatham Cottage by the Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
If a true Cape Cod cottage is what you are looking for, your search ends here. Steps from Schoolhouse Pond, you can for ...
From $386 per night (USD)
VRBO
From $228 per night (USD)
Expedia
THE BOAT HOUSE LOFT ~ RELAXING & PRIVATE WATERFRONT HOLIDAY ~ SHORT & LONG TERM
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
~RATES STARTING AT ONLY $199/ NIGHT ~SHORT TERM BOOKINGS AVAILABLE ~OFF SEASON WEEKLY DISCOUNTS AVAILABLE Welcome to ...
From $228 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Bright & nautical beach home with enclosed yard & outdoor shower - walk to beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summer Get Away Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $310 per night (USD)
VRBO
From $735 per night (USD)
Expedia
Spacious Home with Private In-Ground Pool!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 18820 - Poolside Pause: Spacious Home with Private In-Ground Pool! The Space: Located in Brewster is Poolside ...
From $735 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Frank's Cozy Cape Cod Beach Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This cozy beach cottage is a perfect getaway for those seeking a classic Cape Cod vacation. The homes positioning on th ...
From $420 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Game Room Walk to Nantucket Sound!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16606 - Chatham Charmer: Game Room Walk to Nantucket Sound! The Space: Nestled between Harwich Port and Chatha ...
From $413 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Cape Cod cottage-Just 150 feet to Sea Street Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cozy cape cod cottage with a 5x8 front screened porch is located just 150 feet to Sea Street beach. Full Bath with ...
From $534 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Immaculately clean 2 bedroom duplex less than .3 miles to Sea Street Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immaculately clean, charming duplex unit completely renovated! Only .3 miles to Sea St beach. Quick walk to local hot sp ...
From $191 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Lovely three bedroom home with access to Swan Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Lovely three bedroom, one bathroom home located in a quiet residential neighborhood. Access to Swan Pond, perfect for la ...
From $201 per night (USD)
VRBO
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Expedia
Three bedroom home-walk to shared private beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Guests of this cozy three bedroom Dennisport cottage will enjoy the use of Oak Street shared private beach (.3 miles awa ...
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Expedia
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VRBO
Neat and clean 3 bedroom cottage-Only.2 mile to Sea Street Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Neat and clean 3 bedroom cottage just a short walk (.2 mile) to Sea St. Beach. Cottage features a newly remodeled kitche ...
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VRBO
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Expedia
Affordable vacation cottage on a large private wooded lot
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Cape Cod vacation cottage on a large private wooded lot. Living area has a mini split A/C and both bedrooms have window ...
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Expedia
From $389 per night (USD)
VRBO
Three bedroom home sleeping 8 overlooking Swan Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy amazing views and stunning sunsets from this three bedroom waterfront home overlooking Swan Pond! Launch your kaya ...
From $389 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Clean and bright 2 bedroom home, .4 miles to the beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Charming, bright and clean two bedroom cottage with an enclosed sun porch that doubles as an additional sleeping area wi ...
From $399 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Cozy 2 bedroom cottage less than a mile to the beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy 2 bedroom cottage with separate dining area, wood floors, open floor plan and vaulted ceiling. Amenities include wi ...
From $239 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Sea Shell Motel - Room 10
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $308 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Sea Shell Motel - Room 33
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
All rooms at the motel are non-smoking and include the use of our beautiful private beach with beach lounge chairs on a ...
From $324 per night (USD)
VRBO
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Expedia
2BR Presidential Ocean Front Soundings Seaside Resort w/Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Dennis Port is centrally located about mid-Cape, which makes it the ideal place to launch out from on a tour of this bea ...
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Expedia
From $239 per night (USD)
VRBO
Completely updated 1 bedroom condo unit-steps to a shared private beach!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Beautiful, bright, condominium with a shared-private beach. From the moment you walk in the door, you will know special ...
From $239 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Lovely 3 bedroom ranch home well maintained by owners
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Lovely ranch home that is well maintained by owners. Warm and charming decor throughout. .2 miles to Raycroft Beach. H ...
From $279 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Cute Cape Cod Cottage 3/10th of a mile to Sea Street Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Quaint, well kept, Cape Cod cottage located in popular Dennisport neighborhood. Perfectly situated only 3/10's of a mile ...
From $430 per night (USD)
VRBO
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Expedia
Three bedroom cottage-Only .2 miles to Sea Street Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Take a short walk to the beach from this 3 bedroom home! Less than a quarter mile to Sea Street Beach! This home is in ...
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Expedia
From $284 per night (USD)
VRBO
Location, Location, Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Comfortable, stylish Cape Cod home close to everything. Beach is .7 miles, Route 6 is 3 miles, Downtown is 1.5miles, Bik ...
From $284 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Walk to the Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Adorable beach house 300 yards from Sea Street Beach. Queen size bed in main bedroom, second bedroom sleeps 4, 1 full an ...
From $432 per night (USD)
Expedia
From $460 per night (USD)
VRBO
New rental, near beach and town, linens included
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedrooms-1 Bathroom-Sleeps 5 Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish tow ...
From $460 per night (USD)
VRBO
From $1232 per night (USD)
Expedia
Stunning Waterfront Home with Hot Tub, Deck, Fire Pits, Office & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stunning lake views from almost every room! This newly remodeled home sits right on beautiful Swan Lake & offers direct ...
From $1232 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Steps from beautiful Swan Pond, and minutes to downtown Dennis Port. Enjoy the spacious fenced-in backyard with a fire p ...
From $286 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Waterfront Home With Dock and Two Water Facing Decks! (2372)
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of ...
From $525 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Beachy 3 bedroom home with central air, just .5 miles to the beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This bright and cheerfully decorated home is located just .5 miles from Sea Street Beach! Beautifully decorated back ya ...
From $339 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Stunning Marsh Views, Near Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16689: Lady Slipper - Stunning Marsh Views, Near Pleasant St. Beach! The Space: Nestled in the serene enclave ...
From $572 per night (USD)
Expedia
From $777 per night (USD)
VRBO
Stroll to Dennis Port beaches, bars, eats +more!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Bring the whole family to our spacious and perfectly situated beach house. Literally steps (8 houses to be exact!) from ...
From $777 per night (USD)
VRBO
From $523 per night (USD)
Expedia
Chatham Vineyard View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this cozy three-bedroom, two-bath cottage nestled on a private cul-de-sac. A bright and sunny sunroom adds ter ...
From $523 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Spacious house within walking distance to Sea Street Beach + Pelham House
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Unwind on Windwood Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $466 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Beach sticker with week long bookings!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
DENNIS BEACH STICKER PROVIDED WITH WEEKLY BOOKINGS (sticker is valid Saturday-Friday and may not be valid for weekly sta ...
From $349 per night (USD)
Expedia
Click For Pricing
VRBO
Bright, dog-friendly property located close to Jackknife Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This bright, dog-friendly rental features a fenced yard and is conveniently located near Jacknife Beach. The property in ...
Click For Pricing
VRBO
From $1251 per night (USD)
Expedia
Spacious 7-bedroom house with WiFi, AC in charming Chatham
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Beautifully decorated family compound features Cottage with 2 bedrooms (1 K, 1 Q) + Loft (4 twin beds), and four (4) "bo ...
From $1251 per night (USD)
Expedia
From $728 per night (USD)
VRBO
Pleasant Street Hideaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to the beauty of Cape Cod in this cozy 3-bedroom, 3-bathroom cottage, just a short stroll from Pleasant Street Be ...
From $728 per night (USD)
VRBO
From $976 per night (USD)
Expedia
Unique Private Chatham Getaway with Lap Pool & Deck Lounge (2403)
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect Chatham retreat—new to the rental market and truly one-of-a-kind. Built right into a hillside, t ...
From $976 per night (USD)
Expedia
Click For Pricing
VRBO
Three bedroom home just .4 miles to Inman Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
New to our 2025 Inventory! Nicely decorated 3 bedroom home on a quiet dirt lane. Take a short .4 mile walk to Inman Ro ...
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VRBO
$Renovated Classic Cape w/ Guest House/ PET FRIENDLY\n14 guests, 7 Bedrooms, 3.5 b$
From $1340 per night (USD)
Expedia
Renovated Classic Cape w/ Guest House/ PET FRIENDLY\n14 guests, 7 Bedrooms, 3.5 b
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Discover this 7-bedroom gem in Dennis. This lovely cottage boasts a mix of cozy rooms, including a king bed, queen beds, ...
From $1340 per night (USD)
Expedia
From $284 per night (USD)
VRBO
ONE Minute walk to BEACH! High end home special! TOP RATED GUEST FAVORITE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Dream Getaway in Dennis Port, Cape Cod! 1 minute walk from the beach! Escape to this newly remodeled Ca ...
From $284 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Wifi, AC, 4 bedrooms, 3 bathrooms, additional sleep space and bonus living room in the lower level
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $532 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Spacious house close to town and beach with AC, W/D, games, deck, & grill
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Seabreeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $457 per night (USD)
VRBO
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Expedia
Charming 3-bedroom house in marvelous Dennis with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind in Dennis at this lovely house. Nestled in a charming neighborhood, this superb property offers a cozy retreat fo ...
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Expedia
From $488 per night (USD)
VRBO
Renovated Cape Cod Retreat
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Nestled on a quiet cul-de-sac close to beaches, come enjoy everything the Cape as to offer. Step inside, and be greeted ...
From $488 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Stunning Cape Home Near Chatham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This pet & family friendly newly renovated home in the heart of the Cape has 3 bedrooms, 2.5 baths, and sleeps 8, making ...
From $601 per night (USD)
Expedia
Click For Pricing
VRBO
Charming Guest House, with Waterviews & Private Beach! Perfect for Fun Weekends!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in South Orleans, this pet-friendly sun-filled Guest House offers 2 large bedrooms and 2 full baths. Located in ...
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VRBO
From $6847 per night (USD)
Expedia
Dennis Family Retreat: Private Pool, Sauna & Beach Fun!
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Summary: Escape to Dennis Retreat, a luxurious Cape Cod house with a private pool, hot tub, and sauna for ultimate relax ...
From $6847 per night (USD)
Expedia
From $801 per night (USD)
VRBO
Luxury Waterfront with Game Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 16693 - Chatham Homecoming: Luxury Waterfront with Game Room! The Space: Perched above the shimmering waters o ...
From $801 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Meticulous 2 bedroom home walk to beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Pristine condition! Beautifully decorated and well maintained two bedroom home with central air conditioning! This home ...
From $420 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Cape Cod Getaway - near Seymour Pond and Rail Trail; Bay Beaches w/in a few mile
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brewster Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $431 per night (USD)
VRBO
From $598 per night (USD)
Expedia
Mooncusser Cottage on Taylor's Pond!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Mooncusser! Fabulous two bedroom (1 king, 2 doubles) with a den (sleep sofa) waterfront cottage on saltwater ...
From $598 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Seymour Sunshine - Cozy Cape Cod Home a Short Walk to Seymour Pond in Brewster
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Seymour Sunshine, a cheerful Cape Cod getaway on a Brewster backroad. Just a short stroll from the calm, clea ...
From $618 per night (USD)
VRBO
From $495 per night (USD)
VRBO
2 Bedroom Condo, Sleeps 6, at Edgewater Beach Resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Edgewater Beach Resort is located in Dennis Port, MA on over 300 feet of picturesque private beachfront overlooking the ...
From $495 per night (USD)
VRBO
From $620 per night (USD)
VRBO
3BR - Large Fenced In Yard, Patio, Near Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location: Located on a dead-end road near the head of Pleasant Bay. This 3 bedroom home offers a large fenced in yard wi ...
From $620 per night (USD)
VRBO
From $1069 per night (USD)
VRBO
NEW! Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $1069 per night (USD)
VRBO
From $385 per night (USD)
VRBO
Family Cape Escape | Game Room, Deck & Near Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Escape to this charming 3-bed, 2-bath Cape Cod retreat in Dennis Port, just a short walk to the beach. Perfect ...
From $385 per night (USD)
VRBO
From $829 per night (USD)
VRBO
Soundside Sanctuary - Chatham Home Close to Forest Beach & The Rail Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Soundside Sanctuary! Nestled in a quiet Chatham neighborhood, this peaceful retreat offers spacious, updated ...
From $829 per night (USD)
VRBO

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