
Holiday rentals with a kayak in Dukes County
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Top-rated rentals with kayak in Dukes County
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House rentals with a kayak

Home in Edgartown
4.6 out of 5 average rating, 5 reviews4 Bedroom/3 Bath Edgartown - 6 Beds - Sleeps 8
VixayRating, 5 stars11 months ago
Accommodation: 5/5 Location: 5/5 Property: 5/5 Charlene(host) was very responsive, accommodating, and flexible with our requests. She went above and beyond to meet our needs. The location was perfect! It is secluded from the busy traffic and close to the beach and Edgartown. The property was spacious and had very cold AC! The couch and sofa were extremely comfortable. The washer and dryer were godsend. Everything made our family felt like we were at home even though we were away from home. We highly recommend this property and wished we were able to stay longer. Great memories were made here and forever embedded into our soul. Thank you Charlene for allowing our family to stay and going above to accommodate our needs!
Guest favourite

Home in West Tisbury
4.91 out of 5 average rating, 43 reviewsPrivate West Tisbury House on Freshwater Pond
DonnaRating, 5 stars9 months ago
This is a lovely home that has everything you need for your vacation on Martha’s Vineyard. What I loved: The drive up to the house. On our first day I thought it was too long and bumpy and by the end of our week I so loved that drive. You’ll pass horses, cows and chickens along the way. When you turn onto the road, there is a farmstand, which has absolutely wonderful items. The great room in the house very comfortably seats eight or 10 people. The home is stocked with games, puzzles, books, as well as handy items such as beach, chairs and coolers The owners welcome you to use any of the items that they have in the home. I felt at home and given the directions that they left, I felt completely comfortable using their things. Very clear, opening and closing instructions Very comfortable home that well suited us and our grown children What I didn’t love: There was construction close enough to the home that we heard very frequent nail guns, hammering, and other construction
Guest favourite

Home in Falmouth
4.95 out of 5 average rating, 96 reviewsSalt Pond Bird Sanctuary Sunset
CherylRating, 5 stars8 months ago
Location, location location this place was perfect. The views and sunset were spectacular. It was exactly as advertised. We had a great time would highly recommend. Thanks so much Eva!

Home in Oak Bluffs
4.86 out of 5 average rating, 29 reviewsSummer/Fall 2025 on the Vineyard!
AnuRating, 5 stars9 months ago
Beautiful house with many amenities. We had a rainy weekend but it would have been wonderful to use the bikes and relax in the backyard. The house is very well kept and kitchen is well stocked. I went with two girlfriends and we had a great time in MV and enjoyed coming back to the house. Thank you Jayna. I would most recommend this house to anyone interested in visiting MV.
Top guest favourite

Home in Tisbury
5 out of 5 average rating, 34 reviewsStunning 4/2.5 Water View, Hot Tub, Dogs ok
ErinRating, 5 stars1 month ago
This beautiful, impeccably clean home was the perfect retreat for my family. The primary bedroom and en-suite bath on the first floor made it incredibly accessible for those with mobility concerns. If you’re a fan of nature, you’ll love the walking trails—just step out the back door and you’re on your way to the lagoon. I especially enjoyed taking our dog on peaceful early-morning walks through the quiet neighborhood, where we spotted all kinds of forest wildlife. Visiting Martha’s Vineyard during the off-season made for stress-free travel to and from all the popular spots. James was beyond accommodating throughout our stay, and I wouldn’t hesitate to recommend this home—or any of his other properties. Thank you so much, James!
Guest favourite

Home in Tisbury
5 out of 5 average rating, 11 reviewsSpacious and homey retreat in Vineyard Haven
LeeRating, 5 stars9 months ago
Sandra’s home and hospitality were wonderful. She has a warm and welcoming home, well appointed with everything you could need for your stay. Her house is located so centrally if you like to be walking distance to Main Street in Vineyard Haven while still being close to roads to every other part of the island. As a host, she was so proactive in helping us access her house, and ensuring we were taken care of. We very much enjoyed our stay there.

Home in West Tisbury
5 out of 5 average rating, 4 reviews5 minutes walk to Lambert's Cove
StanleyRating, 5 stars8 months ago
my wife and i spent a thoroughly enjoyable week in late september in william's charming cottage on lambert's cove. even in when when it's grey and chilly outside, it's a comfortable and cheerful place to be. the large window in the living room affords a striking view of the james pond and the dunes separating it from lambert's cove. it's a short walk to the beach, with its crystal-clear water and golden sand.

Home in Oak Bluffs
4.96 out of 5 average rating, 23 reviewsWaterview Home in Sengekontacket Association
MargauxRating, 5 stars9 months ago
Our family had a great a stay. The house is comfortable and inviting, the kind of place where you don’t spending time on a rainy day. Comfortable furniture and beds, lots of games, plenty of space to hang out together and also quiet spots to be alone. The screened in porch was such a treat, with a beautiful view. The host was very helpful and responsive when we needed to be in touch. Everything was lovely!
Cottage rentals with a kayak

Cottage in Chilmark
4.88 out of 5 average rating, 8 reviewsChilmark, Martha' s Vineyard Water View Cottage
ArthurRating, 5 stars9 months ago
We had an excellent week at Robert’s cottage. Just what we needed to get away for a while. The cottage was extremely comfortable and well equipped. The surrounding property was beautiful and very peaceful. We would definitely return again to stay!
Guest favourite

Cottage in Chilmark
4.88 out of 5 average rating, 16 reviewsMarthas Vineyard Cottage - Path To Menemsha Beach
MarekRating, 5 stars1 month ago
The place exceeded our expectations. The location is incredibly peaceful, with stunning west-facing views—perfect for watching sunsets. We stayed with our two dogs, and the walk to the beach was absolutely gorgeous. Just a short stroll through a meadow and forest leads you to a beautiful beach and one of the best fish markets on the East Coast. The variety of seating options is fantastic—you can relax on the grass in front of the house, lounge on the porch, stay protected from insects on the covered patio, or get cozy inside. We’ll definitely be coming back. We loved our stay and made some truly beautiful memories.
Top guest favourite

Cottage in Westport
5 out of 5 average rating, 18 reviewsWaterfront Two Bedroom Cottage
JimRating, 5 stars10 months ago
This was our 4th stay here and it only gets better and better. The house is always extremely welcoming and ready for fun and relaxation. The house is well equipped (kitchen and games/activities) for all your needs and my family can’t wait until next time!
Guest favourite

Cottage in Falmouth
5 out of 5 average rating, 11 reviewsCheerful 4 bedroom cottage in Woods Hole!
ElizabethRating, 5 stars8 months ago
What a brilliant comfortable and relaxing time we had at Robert’s place. We had everything and more that we needed. Beautiful location, cosy and clean house, facilities top notch and comfortable beds. I could not say enough kind things about Robert! Responsive and pro-active, he made our stay even nicer with the loan of bikes. Thanks to him and his family we had a trip of a lifetime with my family. Unforgettable, hope to return again one day!
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Brown University
- Duxbury Beach
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Point Judith Country Club
- Coast Guard Beach
- Roger Williams Park Zoo
- Owen Park Beach
- Oakland Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- South Shore Beach
- Second Beach
- Fort Adams State Park
- Goddard Memorial State Park
- Pawtucket Country Club