
Holiday rentals with a kayak in West Tisbury
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Top-rated Accommodation with a Kayak in West Tisbury
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Holiday House Rentals with a Kayak

* Walk to the beach - Swiss Beach House! *
The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

Waterfront paradise in Falmouth
Wow! Wow! Wow! Congratulations on the beautiful renovation. This was our second stay at this gorgeous home and, while we knew that they were doing some additional work in the off-season, we were not prepared for all of the incredible improvements that were made. This place leaves nothing to be desired. Beds are comfy with lovely linens, lots of room for everyone to spread out (important to us with both teenagers and littles) and lots of toys to use on the pond with a great eye for safety. We have family at Jenkins Pond and make this trip every year. As long as this house is available, we will look no further for a place to stay. Dar is a gracious host, extremely responsive, helpful and accommodating. He clearly put a lot of love and thought into this home and we were very grateful to be guests. It was the best home base for a fun week with family and we once again head home with wonderful memories.

Treat Yourself with King Beds & Sauna & Bar Shed
Great place to enjoy the Cape. The house itself has all high end amenities (nice Weber and Blackstone grill, easy to operate sauna, awesome fire pit, nice high appliances, Lutron lights, minisplits, etc.). You can tell the owner spends time putting an investment to the property. Host was super responsive and very friendly. The location is great for families and made it easy for us given we were bringing dogs. For a pet friendly place, cleanliness was perfect. My kids loved all the fun toys and games that were provided and we ended up outside most evenings. Definitely recommend!

Waterfront New Cottage Private Beach
What a cool spot! Stayed a couple nights with friends for a "Book Retreat" and had the best time reading in the Hammock, chatting by the fire pit, and cooking together in the kitchen.

Cape Cod Life is Good Rentals
This was a great place for a large family. The kids especially enjoyed riding bicycles through the neighborhood. The house was spacious and comfortable. We plan to stay again.

Private Lake Beach | Spectacular Views & Amenities
This is an absolutely beautiful rental and location. Cleanest, most pristine location we have been to. Appliances and bathrooms are glimmering. Host is immediately responsive and kind. 10 out of 10 in all respects.

Riverview Retreat Getaway 30 min- Newport/Cape/PVD
This home is located in a beautiful area. We loved watching the swans and geese in the water. The home is very comfortable. It was perfect place for our family to gather to celebrate my 75th birthday. I highly recommend it.

Vineyard Haven Walk to Ferry
We had a lovely stay at this home! It was quaint and charming, very close to town and had everything we needed. Definitely recommend!
Cottages with a kayak

Spectacular Beach- front home, includes linen
Excellent stay. Plenty of room for the 5 of us. We rested well and were able to relax. We appreciated having laundry on site since we were on a 10-day trip. The beds were comfortable and we slept well. But that is a minor detail when you can watch the sunset over the peaceful water. Lisa communicated well and responded quickly. The house is easy to get to and stores are easy to travel to. Excellent location.

Compass Rose Cottage ★ Steps to Flax Pond & Trails
As soon as I walked into Carol’s place, I felt right at home. In fact, I was sad I couldn’t stay longer. Dennis is a great centrally located area on the Cape (next to many great restaurants and a supermarket). The cottage itself is in a quiet neighborhood right in front of Flax Pond (great for kayaking). It was well stocked with amenities and things to do I could just spend all day there. Carol was friendly and responsive. I would book at the Compass Rose Cottage again!

Payton's Place is your beach get away.
This was our second time staying at Peyton's Place and probably not the last! We love the homey, beachy vibe of the house. We can imagine all the family memories there. There's plenty to walk to and keep two teen girls entertained... the kayaks are much appreciated. Just steps to the beach makes it easy to pop home for lunch or go to beach for an evening walk. There's a new shop in town that I highly recommend... Tide and True. Stephanie is a very responsive and helpful host.

Seaside Cottage - Steps to Beach/Close to ferry
We LOVED our stay! Sloane’s home was a perfect place for our sister getaway! The cottage was adorable and cozy! We enjoyed having coffee in the front room, relaxing on the back deck and slept great in the beds! The neighborhood was so quiet! Just a few folks walking their dogs! 🥰 We enjoyed walking on the beach, taking the ferry for a day trip to Martha’s Vineyard, eating supper & ice cream in New Bedford and did a quick day trip to Hyannis Port! This definitely checked off our ‘Cape Cod’ bucket list! Sloane was a great host with good recommendations and quick and friendly responses! Would definitely recommend her place for a quaint getaway!

Beach house- walk to ocean + 2 min to Craigville
Our family had a wonderful time in Barnstable! Lynn and Ken were extremely responsive and did a great job at communicating when needed. The house was perfect for our family of three. Everything was clean and appeared exactly as the photos presented. We loved spending time on the screened in porch and the outdoor shower was a plus. Being less than 5 minutes from Craigville Beach was ideal along with the use of the beach pass. We would recommend this listing to anyone without hesitation and hope to book again for a future stay!

Cozy 2-bedroom Cottage by the Pond
Leah responded to my booking request within minutes. This was so important because our previous reservations fell through. This was a last-minute booking and I’m so thankful that I was able to find such a wonderful location. Everything that was in the listing was accurate and we felt right at home after an easy check-in process. I cannot thank Leah and Brandon enough for their willingness to let us rent their beautiful cottage last minute. The home is fully stocked with anything that we may have needed. It was a little chilly, but the space heaters were enough to get us through the chilly nights. My kids and I were able to watch Halloween movies on the TV while gazing at the full moon from the skylight above in the living room. I’m looking forward to going back to Massachusetts in the future. There are so many different things that this town and surrounding towns offer.

Little Boho Retreat by the Beach
My partner and I had a lovely weekend getaway at Felicia's sweet place. We had everything we needed and we'd definitely visit again. Everything was as described and the location was perfect. Thank you Felicia for everything you do to make your guests feel welcomed.

* Rustic Cape Cod Captain's Quarters Cottage
Wonderful place! Was completely accurate to what was shown on the listing, great place for a vacation. Super convenient to get to surrounding big towns, but the area itself was peaceful and quiet. 30 second walk to the water, and a beautiful view! Hosts were responsive and super helpful- even though we didn't stay at their place during "prime Cape Cod season", they were helpful in giving us suggestions on what we could still do during this time of year (many suggestions of which we used)! Will definitely look to stay here again in the future, maybe during the summer next time!
Quick stats about holiday rentals with a kayak in West Tisbury
Total rentals
20 properties
Nightly prices starting at
$251 AUD before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- 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