30 Best Massachusetts Vacation Rentals - Vacation Homes, Cabins and Condos in Massachusetts

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HOUSE

Carpe Diem at Nantucket Retreats

Nantucket, MA

Overlook the moors of Forever Wild Sanctuary and Polpis Harbor from Carpe DiemNew for 2019 - Pool and fire pit! The photos in the photo gallery of the pool and fire pit are included only to show what the finished product will look like. These few...

Pool Hot Tub

6 Bedrooms |

8 Bathrooms |

Sleeps 14

$2,686 to $5,204/night

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HOUSE

SeaWatch

Nantucket, MA

SeaWatch is an oceanfront dream in Quidnet Treat your group to a captain's view of the Atlantic Ocean and Sesachacha Pond at SeaWatch, an exceptional vacation rental at the edge of the ocean complete with beach access and a separate guest house....

4 Bedrooms |

4.5 Bathrooms |

Sleeps 8

$1,511 to $3,189/night

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HOUSE

C365 Willinsky

Charlestown, RI

Beach: Charlestown Beach Charlestown By The Sea. This home offers the perfect retreat after a day at the beach or sightseeing. A light and airy contemporary it has central air, spacious bedrooms. It is clean, bright and nicely appointed on quiet...

3 Bedrooms |

2 Bathrooms |

Sleeps 7

$289/night

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HOUSE

C417 Nutmeg Lane

Charlestown, RI

Amenities:Allow PetsBeach Location Type - Walk to BeachBedding 2 - QueenBlenderDining Seats - 6Distance to Beach - 0.5-1 mi.Full KitchenLobster PotNearby Grocery StoreNearby MedicalNearby PlaygroundNumber of Bathrooms - 1Stove -...

Pets OK

2 Bedrooms |

1 Bathroom |

Sleeps 6

$342/night

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HOUSE

Daisy Street Home 12

Harwich, MA

Boasting classic Cape Cod style and a prime location just 200 steps from Long Pond, this 4BR/2BA cottage offers the perfect home base for your vacation. Spend your days fishing, swimming, and boating on Long Pond, the largest freshwater lake on Cape...

FREE CANCELLATION

4 Bedrooms |

2 Bathrooms |

Sleeps 8

$185 to $415/night

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DUPLEX

Lower County Road Duplex

Dennis Port, MA

Host your next family get together at this quaint 6BR/2BA duplex cottage. This rental includes two identical side-by-side units -- each with a full-size kitchen, living area, and awesome outdoor space. Hang out on comfy furniture on the front porch...

FREE CANCELLATION

6 Bedrooms |

2 Bathrooms |

Sleeps 12

$211 to $516/night

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HOUSE

C382 Linehan

Charlestown, RI

Enjoy plenty of open living space in this reverse living beach home with pretty views of Ninigret Pond. This 4 bedroom, 2 bath home will comfortably sleep 7 people. The upper floor living area offers an open living room, kitchen and dining area with...

4 Bedrooms |

2 Bathrooms |

Sleeps 7

$355/night

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DUPLEX

460 Lower County Road Duplex Right Side Unit

Dennis Port, MA

Walk everywhere from this cute 3BR cottage! Enjoy an amazing outdoor space, including a quintessential front porch with lounge furniture and a shared yard that has an outdoor shower, grill, and shaded al fresco dining. Your rental commands a prime...

FREE CANCELLATION

3 Bedrooms |

1 Bathroom |

Sleeps 6

$106 to $260/night

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HOUSE

C021 Howard (3-Bedroom Home)

Charlestown, RI

Neighborhood: Charlestown Beach: Charlestown Beach This comfortable home is yours to enjoy on your vacation. It has an open living, dining and kitchen areas. There are three nice sized bedrooms; the master bedroom with its own bath and two...

3 Bedrooms |

2 Bathrooms |

Sleeps 8

$202/night

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APARTMENT

C400 Caswell

Charlestown, RI

Beach: Blue Shutters Beach: Blue Shutters Beach, East Beach, Charlestown Beach, Ninigret Pond, Burlingame State Park/Watchaug Pond COMES WITH BEACH PASS TO BLUE SHUTTERS BEACH AND CHARLESTOWN BEACH Our place has a large backyard with plenty of...

3 Bedrooms |

1 Bathroom |

Sleeps 6

$153/night

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HOUSE

C197 Perry (3-Bedroom Home)

Charlestown, RI

Just a short walk to Charlestown Beach from this 3 bedroom, 2 bath Cottage. There is a double sleep sofa in the family room/den for extra sleeping space. Distance to the Charlestown Beach is approximately 0.25 miles and a really short walk to...

3 Bedrooms |

2 Bathrooms |

Sleeps 6

$232 to $300/night

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HOUSE

C323 Kahn (3-Bedroom Home)

Charlestown, RI

Privacy by the beach…this spacious, comfortable 3 bedroom, 4 bath home sleeps 10. There is a fourth room over the garage which is a great sleeping area for the kids and their friends. There are many areas to hang out with friends and family or...

3 Bedrooms |

4 Bathrooms |

Sleeps 10

$300 to $422/night

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HOUSE

C403 Orsini (4-Bedroom Home)

Charlestown, RI

Make your summer memories here at this well maintained home in Charlestown! Located roughly 1/2 mile from Charlestown Beach it has sleeping for 10 guests. There are two levels each with it's own kitchen,living,dining space which is ideal for two...

4 Bedrooms |

2.5 Bathrooms |

Sleeps 10

$245 to $367/night

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HOUSE

C402 Willow (2-Bedroom Home)

Charlestown, RI

Lasting summer time memories are made here in this comfortable 2 bed room, 1.5 bth. An over-sized deck located on the south side of the house is large enough to grill and dine out on. A Charlestown town beach pass is provided . This pass allows you...

2 Bedrooms |

1.5 Bathroom |

Sleeps 8

$116 to $220/night

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COTTAGE

C396 Schroeder

Charlestown, RI

Beach: West Beach *Classic Rhode Island beach cottage with full view of the ocean & Block Island * Located on private West Beach in Charlestown, RI *Rental comes with beach privileges * Porches on three sides for both shade and sun relaxing...

Pets OK

4 Bedrooms |

1 Bathroom |

Sleeps 9

$202 to $458/night

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HOUSE

C389 Lorenzo

Charlestown, RI

Enjoy panoramic views of Charlestown Beach and Ninigret Pond from the upstairs level of this well cared for home! The large open space and vaulted ceiling on this floor make up the well equipped kitchen, dining, living room and half bath. Lots of...

3 Bedrooms |

1.5 Bathroom |

Sleeps 8

$544/night

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HOUSE

C164 Colby (3-Bedroom Home)

Charlestown, RI

Bring your boat ( up to 19ft) and keep it at the dock in front of this peaceful 1960's cottage on Ningret Pond-( direct access to the Ocean). Ranch in private wooded setting on cul-de sac with wonderful water views of salt pond from kitchen/ living...

3 Bedrooms |

2.5 Bathrooms |

Sleeps 6

$196 to $300/night

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HOUSE

C413 Alper (2-Bedroom Home)

Charlestown, RI

This delightful home is located just a short walk to Green Hill Pond and 1.5 miles to Charlestown Town Beach. With two lovingly furnished bedrooms, one with full master bath and a full bath with laundry to accommodate the second bedroom, spacious...

2 Bedrooms |

2 Bathrooms |

Sleeps 6

$183 to $220/night

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COTTAGE

Small Cottage | Woods Hole

Woods Hole, MA

Follow the dirt road to our 2BR (sleeps 4) cottage by the sea. With charming yet modernized character as well as a private beach plus access to the Shining Sea Bikeway, our rental offers you the chance to truly explore Cape Cod. Walk or bike to...

FREE CANCELLATION

2 Bedrooms |

1 Bathroom |

Sleeps 4

$238 to $717/night

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CONDOMINIUM

Cape Townhouse Unit 11

Brewster, MA

ThisThis charming 2-bedroom, 2-bath plus a loft townhouse promises a fantastic stay on the Cape! Newly renovated and filled with natural light, this rental features warm wood floors and modern marble-touched bathrooms. Brewster is famous for its...

FREE CANCELLATION

2 Bedrooms |

2 Bathrooms |

Sleeps 6

$299 to $418/night

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DUPLEX

Dennisport Duplex by the Beach

Dennis Port, MA

Look no further, you’ve found the perfect Dennisport vacation rental! This delightful duplex is only an 8-minute walk from popular Sea Street Beach, and just a short stroll to ice cream, dining, and more. Sleeps 8. The 4BR/2BA duplex is comprised...

FREE CANCELLATION

4 Bedrooms |

2 Bathrooms |

Sleeps 8

$161 to $461/night

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HOUSE

Wooded Chatham Home on the Monomoy

Chatham, MA

Wooded 3BR, 2BA Chatham Home on the Monomoy with Hot Tub & Kayak Launch This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the...

Hot Tub

FREE CANCELLATION

3 Bedrooms |

2 Bathrooms |

Sleeps 6

$249 to $498/night

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HOUSE

8 Peck's Way Orleans Home

Orleans, MA

Kayakers and nature lovers take note! This 4BR, 2BA (sleeps 8) house sits on 7+ waterfront acres in Orleans, offering extraordinary privacy with exquisite water views of historic Arey's Pond, part of Pleasant Bay. Note: this is a salt water pond....

FREE CANCELLATION

4 Bedrooms |

2 Bathrooms |

Sleeps 8

$158 to $534/night

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HOUSE

43 Santuit Ln Home at Mashpee

Mashpee, MA

This four-season vacation home is designed for comfort and family fun. In warm weather, pick up fresh lobster for your crew, and enjoy a seafood feast on the deck overlooking the lake. During chilly months, reconnect with loved ones in the spacious...

FREE CANCELLATION

3 Bedrooms |

3.5 Bathrooms |

Sleeps 10

$418 to $749/night

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HOUSE

265 Main Street House

Wellfleet, MA

Gaze out at the charms of downtown Wellfleet from your second-floor balcony in this 4BR/3BA home. Restaurants, shops, and the coastal town’s famous galleries are just steps away. Head down Main Street towards the Town Pier, Mayo Beach, and...

FREE CANCELLATION

4 Bedrooms |

3 Bathrooms |

Sleeps 8

$224 to $912/night

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HOUSE

40 Epanow Home at Eastham

Eastham, MA

Property Overview Featuring miles of unspoiled shoreline and warmer bay beaches, Eastham is a sure bet for your next Cape Cod getaway. An ideal place to relax, this two-story 5BR/2.5BA home offers 2,274 square feet of comfortable living space --...

FREE CANCELLATION

5 Bedrooms |

2.5 Bathrooms |

Sleeps 10

$231 to $806/night

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HOUSE

200 Shurtleff Rd Home

Eastham, MA

Situated less than 50 yards from a private Association Beach on Cape Cod Bay, this 3BR/2BA Eastham home is perfect for the relaxed coastal vacation you’ve been dreaming about. Enjoy lazing on the sand, swimming in the waters, and strolling along...

FREE CANCELLATION

3 Bedrooms |

2 Bathrooms |

Sleeps 6

$305 to $704/night

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HOUSE

46 Paola Dr Home at East Falmouth

East Falmouth, MA

Picturesque views of Bournes Pond await from this quaint 4BR/2BA East Falmouth home. Enjoy a great location just minutes from downtown Falmouth and the Martha's Vineyard ferry and surrounded by opportunities to paddle board, fish, clam, and kayak....

Pets OK

FREE CANCELLATION

4 Bedrooms |

2 Bathrooms |

Sleeps 8

$162 to $499/night

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HOUSE

49 Brooks Home at Harwich Port

Harwich Port, MA

This spacious 4BR/2.5BA Cape Cod home is just a five-minute walk from the beach. After a day in the sun, unwind in the shady backyard. Throw a BBQ or just relax in the hammock. Nautical décor and multiple living spaces, including three living rooms...

FREE CANCELLATION

4 Bedrooms |

2.5 Bathrooms |

Sleeps 8

$166 to $744/night

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HOUSE

Walkable Falmouth Hts Beach Home

Falmouth, MA

Bring the whole gang for a quintessential Cape Cod getaway at this adorable and spacious 5BR, 1.5BA (sleeps 10) bungalow. Park your car and leave it—you’re within walking distance of Falmouth Heights Beach, ferry to Martha’s Vineyard and Cape...

Pets OK

FREE CANCELLATION

5 Bedrooms |

1.5 Bathroom |

Sleeps 10

$228 to $622/night

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