Holiday Homes in Cuttyhunk

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Featured Holiday Homes in Cuttyhunk

Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!

9.8 out of 10, Exceptional, (76)
"Derek was incredibly helpful and responsive, and the place was perfect! "
The price is NZ$530
includes taxes & fees
23 Feb - 24 Feb
Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Walk to beaches. Huge deck, roof-deck, new kitchen, close to town

10.0 out of 10, Exceptional, (117)
"Had a wonderful time! This was our second stay at the house- perfect size for our group of 15. Super close to "
Walk to beaches. Huge deck, roof-deck, new kitchen, close to town

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (56)
"This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (190)
"Once again, we enjoyed our family Christmas on the Cape in our favorite area. This house has everything you will need for a comfortable stay. The house is immaculate and completely stocked. The beds are extremely comfortable, there is plenty of room for our entire family to enjoy themselves and Roberta was so easy to communicate with if needed. We will definitely stay here again. "
The price is NZ$891
includes taxes & fees
24 Feb - 25 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (5)
"This house is spectacular and we cannot wait to rent again. There’s nothing to complain about except we didn’t rent it longer. "
The price is NZ$3,200
includes taxes & fees
27 Feb - 28 Feb
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Luxury Beach House, Easton Point. Ocean Views, 2 Master BRs, Walk to Everything

10.0 out of 10, Exceptional, (93)
"The home was well maintained and fully stocked with the things needed for a comfortable stay."
Luxury Beach House, Easton Point. Ocean Views, 2 Master BRs, Walk to Everything

sea breeze house at sakonnet point. RE. 03495-STR

9.2 out of 10, Wonderful, (52)
"This was at least the third time we have stayed at the Sea Breeze House at Sakonnet Point. As before we had a lovely stay. The sunsets are beautiful! Thank you for another great stay. "
sea breeze house at sakonnet point. RE. 03495-STR

Country Farmhouse, Old Vineyard charm, New Amenities, Central AC, 2 King beds.

9.6 out of 10, Exceptional, (4)
"Nice and Quiet place. Would book again!"
Country Farmhouse, Old Vineyard charm, New Amenities, Central AC, 2 King beds.

Elisa's Cottage - Your Family Vacation Destination

10.0 out of 10, Exceptional, (5)
"We chose Elisa’s Cottage for a weekend visit with friends who live in the area. We could not have made a better choice. Andrew has thought of everything guests might need. The house is immaculately clean and thoughtfully decorated. It is spacious and comfortable. The location is quiet and private. Andrew met us at check in to make sure we had everything we needed. The goodies in the welcome basket were a nice touch! Thank you Andrew’"
Elisa's Cottage - Your Family Vacation Destination

Near Bikeway, Quaint Village Center, and Beaches! Renovated, Great Natural Light

9.4 out of 10, Exceptional, (15)
"Charming home...lots of natural light. Wonderful location to walk to town and restaurants! Owners great to work with. "
Near Bikeway, Quaint Village Center, and Beaches! Renovated, Great Natural Light

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

10.0 out of 10, Exceptional, (61)
"We really enjoyed our time at the cottage! This is a spectacular location with the very short walk down a wooded path to the beach at Lambert's Cove. It was a nice location for food and shopping at Vineyard Haven and visiting our friends in Chilmark. I recommend you arrive during daylight hours as we did - I think it might be tough to find the place for the first time at night. Also, the size of the cottage is perfect for a couple but would work well with one or two small children in the smaller...
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

Dog-friendly, lakefront home with roof deck - blocks from the beach

8.0 out of 10, Very good, (32)
"Great location between the ponds & ocean. Great deck & family rooms to entertain in. Beautiful Kitchen. Smaller EIK area but definitely doable.. a few negatives do exist though. There's a row boat in the photos down by the pond on this property. I just assumed , as with other beech properties, we would be able to use it & was very much looking forward to that. The boat has a hole in it making it unusable,, The furnishings are from 60's 70's but we still love the interior of the home. It was...
Dog-friendly, lakefront home with roof deck - blocks from the beach

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

10.0 out of 10, Exceptional, (21)
"My wife, 2 dogs and I visited for a week. This house was well appointed, clean and relaxing. The deck, yard and views are spectacular. We were looking for a quiet place to decompress and recharge and this house did the trick. Christian was very responsive and helpful to every question. I highly recommend."
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

Family Home That Is Walking Distance To Town and Ferry

10.0 out of 10, Exceptional, (24)
"Convenient to everything in a very quiet neighborhood"
Family Home That Is Walking Distance To Town and Ferry

Immaculate Luxury home, water views to Vineyard, private beach, bike path & more

10.0 out of 10, Exceptional, (19)
"This house was the best we have rented on Cape Cod. There was ample space for 6 adults. The deck was beautiful and helpful to have a screened in porch if there were bugs at night. Highly recommend!"
Immaculate Luxury home, water views to Vineyard, private beach, bike path & more

Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

9.8 out of 10, Exceptional, (21)
"Very clean, spacious open concept. Easy walk to town. Very responsive host . For example, when the coffee maker died a new one magically appeared on the front doorstep in short order. Would stay again!"
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

Middletown Bungalow - RIBryan Property

9.0 out of 10, Wonderful, (7)
"Enjoyed our overnight stay. Nice, clean and comfy place."
The price is NZ$1,029
includes taxes & fees
23 Feb - 24 Feb
Middletown Bungalow - RIBryan Property
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cuttyhunk

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (158)
"This is the 4th time I've stayed at an Inn Season resort in Falmouth. There are 3 properties available and they are all quite nice. This visit was at Captains Quarters overlooking Heights Beach. It was a winter weekend with a steady fall of very fine snow. The accommodations are always spot on. It was picturesque and a perfect weekend getaway to relax and unwind. "
The price is NZ$241
includes taxes & fees
24 Feb - 25 Feb
InnSeason Resorts Captain's Quarters

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

9.8 out of 10, Exceptional, (120)
"This is our 4th time staying- love "
The price is NZ$290
includes taxes & fees
3 Mar - 4 Mar
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!

9.8 out of 10, Exceptional, (76)
"Derek was incredibly helpful and responsive, and the place was perfect! "
The price is NZ$530
includes taxes & fees
23 Feb - 24 Feb
Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.