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Compare 423 Vacation Homes in Cuttyhunk with updated reviews, rates, and availability.

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.

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

9.8 out of 10, Exceptional, (71)
"The bungalow is in a great location. Easy to walk to beach and easy to explore the area. The 2 car parking was a plus. "
The price is AED 364
AED 1,119 total
includes taxes & fees
12 Jan - 13 Jan
Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!

A Vineyard Home Perfect For Family Gatherings

9.0 out of 10, Wonderful, (29)
"In a safe, quiet neighborhood, a true Family beach house/Cabin. Very roomy. "
A Vineyard Home Perfect For Family Gatherings

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

10.0 out of 10, Exceptional, (116)
"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

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.

A View Fit for Royalty!

10.0 out of 10, Exceptional, (20)
"Wonderful property, very well kept. Great idea of having everything neatly labelled in the kitchen ! We were there for a birthday and host very kindly added some birthday decorations prior to ours checking in. Couldn't have been happier with the experience! "
A View Fit for Royalty!

Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet

10.0 out of 10, Exceptional, (12)
"My family has deep roots at the Cape, so while we don't currently live there, we try to return each summer. This was our first try at a rental-rather than hotel-and it was superb!! I was looking for a place to fit myself, my husband, my sons, our dog, and my older parents. This spot was perfect in every way. We had such a great time, and bonding experience and the host was stellar in her communications and helpfulness. We fit comfortably, the accommodations were clean and cozy, and the beach was...
Quiet duplex by the beach, short walk to Falmouth Village, 1GB Internet

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

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (5)
"Perfect home for a family holiday. This is one of those rare listings where the house is nicer than even the pictures make it seem. Already planning to rent again."
The price is AED 2,571
AED 6,375 total
includes taxes & fees
21 Jan - 22 Jan
The Beach Estate, Panoramic Ocean Views, 5700 sqft

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

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

10.0 out of 10, Exceptional, (56)
"This place was perfect for us! We had a family reunion of 14 young and old adults and everyone loved the place. The kitchen is fabulous, the bed was super comfortable and we could all gather together or spread out among the many comfy sitting rooms loaded with books. The location couldn’t be more convenient. Our only complaint was a few rainy days. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Vineyard Haven, Quiet Setting Just Minutes from Ferry and Bus

9.4 out of 10, Exceptional, (70)
"Great stay I liked the fact I could rent for 4 Nights the hose was Beautiful unfortunately it was hot“Wifey” wanted AC😂😂Son was disappointed Grill did not work"
Vineyard Haven, Quiet Setting Just Minutes from Ferry and Bus

Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

9.8 out of 10, Exceptional, (49)
"This vacation home is amazing! So spacious and clean. The beds were very comfortable and the location is perfect! The Host was excellent and so responsive to any questions that we had and was so accommodating. By far the best rental experience we have ever had."
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

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

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

Walk to Newport, 1st & 2nd Beaches, & Cliff Walk from this Newly Redone Home

9.8 out of 10, Exceptional, (20)
"This is a very nice, cozy home. Super convenient to everything and in a nice development. Furnishings are nice, comfortable and home very clean. Communication with owner very good. Just, FYI - the mattresses I believe are the “Casper” type and thus quite soft. "
Walk to Newport, 1st & 2nd Beaches, & Cliff Walk from this Newly Redone Home

Middletown Bungalow - RIBryan Property

9.0 out of 10, Wonderful, (7)
"Enjoyed our overnight stay. Nice, clean and comfy place."
The price is AED 786
AED 2,076 total
includes taxes & fees
12 Jan - 13 Jan
Middletown Bungalow - RIBryan Property

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat

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

10.0 out of 10, Exceptional, (189)
"This was our second stay at Roberta’s lovely home. The house is in a great location (very nice area, close to everything) and is very comfortable. There were 5 of us and there was plenty of room. The kitchen is very nice and was great for preparing Thanksgiving dinner- plenty of seating in the dining area. The house was very clean, nicely decorated, with a great backyard. Roberta is a great host- very responsive and helpful- she had the fridge stocked with water and cream for coffee as well...
The price is AED 661
AED 1,904 total
includes taxes & fees
12 Jan - 13 Jan
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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, (157)
"Great place right on the water "
The price is AED 463
AED 530 total
includes taxes & fees
13 Jan - 14 Jan
InnSeason Resorts Captain's Quarters

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

9.8 out of 10, Exceptional, (118)
"We stayed five days. The cottage was so cozy and very clean with high end appliances. The area is quiet and lots of grass. Perfect for dog parents. Great location, a short drive to Newport. Loved the heated floor in the bathroom! "
The price is AED 474
AED 609 total
includes taxes & fees
13 Jan - 14 Jan
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.

9.8 out of 10, Exceptional, (70)
"Between the beautifully landscaped yard and the proximity to the ocean, this is a fabulous place! We love walking to the ocean for our am and pm walks, The Shining Sea Bike trail is also very close and just a joy! Property owners were great to work with. Definitely will stay here next year. Thanks for a great stay!!! "
Quiet duplex by the beach, short walk to Falmouth Village, 1 GB Internet.
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.