
Vacation rentals with a kayak in Dukes County
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Top-rated kayak rentals in Dukes County
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.
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House rentals with a kayak

Home in Oak Bluffs
4.81 out of 5 average rating, 31 reviewsCozy, Clean, Bikes, Kayaks, Lagoon
AlisonRating, 5 stars9 months ago
We loved staying at Steven’s place. My teenage daughter and her friend loved having their own room as well as some late night ping pong games in the basement! I appreciated having a washer and dryer as well as the cookware and dining room to make a couple of nice dinners at the house. We’d love to return in the future and highly recommend it!

Home in Edgartown
4.6 out of 5 average rating, 5 reviews4 Bedroom/3 Bath Edgartown - 6 Beds - Sleeps 8
VixayRating, 5 stars9 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 favorite

Home in Falmouth
4.95 out of 5 average rating, 96 reviewsSalt Pond Bird Sanctuary Sunset
CherylRating, 5 stars6 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!
Guest favorite

Home in Edgartown
5 out of 5 average rating, 13 reviewsWell appointed, meticulous, 3 bedroom home
NathanielRating, 5 stars20 months ago
Kim’s place was exactly what we were looking for on our Vineyard vacation. Plenty of space, well appointed and updated. Location was great with plenty of outdoor space. Kim reached out with plenty of detail and was helpful along the way. Look forward to returning next summer!!

Home in Edgartown
5 out of 5 average rating, 3 reviewsChappy's Pole House: A Luxurious Bohemian Escape
LynnRating, 5 stars9 months ago
The pole house was extremely clean, aesthetically pleasing, and comfy. Leda was very friendly and there were lots of details that went into making us comfortable as guests! The entire property is beautiful and we had a great time using all of the amenities. Check in and check out was very flexible!

Home in Chilmark
4.94 out of 5 average rating, 16 reviewsOcean view mid century modern prvt beach + LV/SQB
PamRating, 5 stars7 months ago
We loved our stay in this beautiful home and enjoyed all the property had to offer. The views were spectacular; and the access to the boats and pond was such a joy. Many happy memories!

Home in Oak Bluffs
4.86 out of 5 average rating, 29 reviewsSpring/Summer/Fall 2025 on the Vineyard!
AnuRating, 5 stars7 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.
Guest favorite

Home in Tisbury
5 out of 5 average rating, 10 reviewsSpacious and homey retreat in Vineyard Haven
LeeRating, 5 stars7 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.
Cottage rentals with a kayak

Cottage in Chilmark
5 out of 5 average rating, 6 reviewsOceanview Cottage
ArthurRating, 5 stars7 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!

Cottage in Chilmark
4.87 out of 5 average rating, 15 reviewsMarthas Vineyard Cottage - Path To Menemsha Beach
KimRating, 5 stars7 months ago
After staying a week at the Ditty Box I did not want to leave. The setting and views from the cottage are better in person (vs. pictures). The cottage was clean, adorable, and stocked with everything I needed (including binoculars :) ) Honestly I checked in, had a dream week on the island, and checked out. No problems or issues ... so I never had to contact anyone. I hope to return soon. Thank you for a wonderful stay!!
Top guest favorite

Cottage in Westport
5 out of 5 average rating, 18 reviewsWaterfront Two Bedroom Cottage
JimRating, 5 stars8 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 favorite

Cottage in Falmouth
5 out of 5 average rating, 11 reviewsCheerful 4 bedroom cottage in Woods Hole!
ElizabethRating, 5 stars7 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
- East Matunuck State Beach
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Bonnet Shores Beach
- Craigville Beach
- Scarborough State Beach
- Hyannis Port Beach
- Duxbury Beach
- Nauset Beach
- Popponesset Peninsula
- Saquish Beach
- Glendon Road Beach
- Horseneck Beach
- Madaket Beach
- Roger Wheeler State Beach
- Galilee Beach Club Beach
- Brown University
- Mohegan Bluffs
- Easton Beach
- Monument Beach
- Fogland Beach
- Sand Hill Cove State Beach