Search Vacation Homes in Cuttyhunk

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Homes in Cuttyhunk

"The living room was moldy, the door doesn’t lock, the insects were in every room; including the bed, the kitchen tools were rusty, the floors were dirty, the place is a mess. The post states a gas grill; there’s only a charcoal grill without any charcoal, the post states resident beach parking pass; there was none, the post states a queen size bed; there wasn’t one. The kitchen floor was completely stripped of tile. Overall the house was dirty and a complete waste of money. The only nice thing...

"The most magical place, thank you for the prefect stay."

"Very enjoyable "

"Central property with all essentials!"

"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."

"Awesome, fun place. Has everything you need for a great Vineyard stay!"

"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."

"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."

Beach nearby, sun loungers, beach towels

"This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody! "

"Property was as presented and the attention to detail throughout the house to ensure we enjoyed the stay was noticed and appreciated! Will definitely recommend Dan and Havens Sanctuary Farm to others!"

"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"

"Very nice house and property in the quietest part of the island. Great thing is that it is only 2.5 miles away from the beach!!"

"The home was beautiful and very well appointed. Easily accommodated our group of 8 adults with room to spare. Minor complaint is that there could’ve been a few more towels available, but the washer and dryer took care of that."

"One of the most relaxing and comfortable places we have ever stayed in on the island. Lots of privacy for everyone and felt comfortable the whole time. Would recommend for large groups! The hosts were great and communicated everything to us in a timely manner. "

On the beach, sun loungers, beach towels

"We had a great stay at Oceans 11! The home is beautiful, it was incredibly clean, and very well stocked! We look forward to staying here again!!"

SAR 1,387 total

includes taxes & fees

23 Sep - 24 Sep

"Location was perfect…a short walk to the beach, a short walk to the Island Queen ferry to Martha’s Vineyard. This quaint house was fairly well stocked and the beds were comfortable. Easy in, easy out with the automated door lock. Would stay here again. "

SAR 2,623 total

includes taxes & fees

10 Oct - 11 Oct

"This place is perfect, My girlfriend and I stayed there for Memorial Day weekend. It’s a quiet little cottage nestled in the wood we loved the privacy and getting away from the hustle and bustle of Oak bluffs at night. I’ve read some other reviews saying that the electricity doesn’t work but it worked for us the whole time. I personally plan on staying there again"

"The closeness to everything"

"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Cuttyhunk Hotel Reviews

Mansion House Inn And Spa

10/10 Excellent

"Great hotel on the island with history"

New Bedford Harbor Hotel, an Ascend Collection Hotel

10/10 Excellent

"We really enjoyed our stay here! The staff was super friendly and made us feel welcome right away. Our room was spacious with lots of natural light, which we loved. The bar attendant was great too- very friendly and fun to chat with. Breakfast was simple but convenient: danishes, oatmeal packets, bagels, premade sandwiches, and boiled eggs in the fridge. There’s a toaster and microwave if you want to warm things up. Just a heads-up, don’t expect the usual hotel spread with waffles, pancakes, or scrambled eggs. :) The location was awesome- restaurants are just a short walk away. Parking was easy too, with the hotel’s lot just a block over, and we felt safe walking back and forth. Overall, we had a great experience and would definitely stay here again!"

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Search Vacation Homes in Cuttyhunk

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Homes in Cuttyhunk

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

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

Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

Cozy cottage 3/4 mile from Oak Bluffs harbor

Quaint,,,Quiet..up island feel yet a short walk to town and harbor

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Sanctuary House: An ocean-view farmhouse retreat

The quintessential MV home. Now booking for 2026!

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Best Kept Secret Retreat for Adults with Water & Golf Course Views!

Oak Bluff's Victorian Walk to Town & Beaches

Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

Charming 2-bd Home Steps to Falmouth Heights Beach w/ Fab Fenced Patio & Yard

Charming newly renovated home in Little Compton.

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

Top Cuttyhunk Hotel Reviews

Mansion House Inn And Spa

Newport Beach Hotel & Suites

Falmouth Tides

Falmouth Inn

Wyndham Newport Hotel

Inn on the Square

New Bedford Harbor Hotel, an Ascend Collection Hotel

Atlantic Beach Hotel Newport

Vineyard Harbor Motel - Private Beach

Explore a world of travel with Expedia

More Accommodation Types in Cuttyhunk