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Top 10 Cuttyhunk hotels and places to stay

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
8.0 out of 10, Very good, (3)
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach
3.0 out of 10, (2)
"We were shocked when we arrived at this property. The word "rustic" should be added to its description. The front door to the property is a sliding glass does that does not from the outside. When we walked through the house upon arriving, we walked through spiderwebs on the inside of the house, the smell of mildew was overwhelming, most of the windows had been screwed closed with no way to open them, there were rodent traps in every room, the mini splits (AC units) worked extremely well, the...
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
8.8 out of 10, Excellent, (9)
"We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back "
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Cozy efficiency apartment/heated pool
9.8 out of 10, Exceptional, (17)
"What a wonderful gem in the woods of Chilmark. The pool is the icing on the cake. Ronnie was such a wonderful host! Hope to return in the fall, but definitely again in the future."
Cozy efficiency apartment/heated pool
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.6 out of 10, Excellent, (22)
"Wonderful place for a getaway to MV. Well appointed, comfy home with great pool. Plenty of privacy but easy to get to. Enjoyed our stay"
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
10.0 out of 10, Exceptional, (44)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Beautiful dog-friendly home with water view, balcony & washer/dryer
7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Cozy Sanctuary with Water Views
Cozy Sanctuary with Water Views
Luxury Home in Exclusive Aquinnah
10.0 out of 10, Exceptional, (12)
"Great house and the host did a great job in answering all of our questions and being available when we needed them."
Luxury Home in Exclusive Aquinnah
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
10.0 out of 10, Exceptional, (5)
"Spent a wonderful week at Lobsterville Landing — a delightful home perfect for time with friends and family. Only a quick walk to the beach, not that we were in a hurry to leave this beautiful home."
Water-view home with large deck, balcony, enclosed sunroom & peaceful location
Modern beach house - Walking distance to Philbin Beach
10.0 out of 10, Exceptional, (27)
"Beautiful spacious home near beach. Perfect setup for our family. Lovely kitchen and deck. You could hear the birds and the waves from the deck. A perfect spot to enjoy this beautiful part of the Vineyard."
Modern beach house - Walking distance to Philbin Beach
Beautiful Aquinnah Home: Ocean View, Walk to Beach
3.0 star property
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
7.8 out of 10, Good, (11)
"Nice and clean property; it’s really back “off the beaten path”."
Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
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.
Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark
2.0 star property
Quaint & Quiet Quitsa: 3-bedroom house with WiFi, AC in peaceful Chilmark
Magical House in the Trees with Water View - Secluded Area
10.0 out of 10, Exceptional, (76)
"Lisa’s home truly is unique. Located in a very beautiful part of the island. It’s far from the ferry (and the crowds :)) so it would be best to stay here if you have a car on island. Ubering could be difficult and expensive. The privacy and fenced in back yard are unbeatable. Comfortable beds, well equipped kitchen, close to gay head and lobsterville beaches. We had such an amazing stay!!"
Magical House in the Trees with Water View - Secluded Area
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
9.8 out of 10, Exceptional, (36)
"Property was as described and the vacation was as prescribed. The home is perfectly secluded on a large (2 acres ??) lot. Views of the sunsets and lighthouse were very nice. The home is humble but comfortable. We did not use the kitchen outside of making coffee but seemed to have what we needed. We didn’t turn on the tv but enjoyed the fireplace. We found spots to read and relax throughout the home. Our pup loved running around the huge property. The neighbor’s collie came by each morning to...
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Private Hillside Home with Open Property and a Fully Equipped Kitchen
9.6 out of 10, Exceptional, (8)
"The house was great"
Private Hillside Home with Open Property and a Fully Equipped Kitchen
Airey Two Bedroom Menemsha cottage
10.0 out of 10, Exceptional, (4)
"Peaceful location near conservation trail and a short drive to Lucy Vincent and the Chilmark Store. Clean, spacious and comfortable for our family of six adults. The owner mailed the key and information about the house ahead of our stay, which was helpful. Highly recommended!"
Airey Two Bedroom Menemsha cottage
Peaceful Chilmark Farmhouse by Menemsha Beach
3.0 star property
Peaceful Chilmark Farmhouse by Menemsha 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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