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

gorgeous waterfront cottage w/4kayaks and 2 SUPs
10/10 stay!! The cottage sits on a beautiful pond. We came during a rainy weekend so we stayed mainly inside. We turned on the electric fireplace & put on a movie. It was so cozy. Once the rain let up, we went outside and used the outdoor fireplace! So peaceful. Everything else you’d need, you are only a short drive from a cvs & grocery store. Melissa is a great host. We really appreciate how quick she responded with any minor concern we had. We look forward to more future stays at the cottage!

Sunburst Cottage on Long Pond
Laurie’s Sunburst Cottage was a perfect location. The view was spectacular each morning, waking up to see long pond. The space was so nicely decorated and very cozy for us to enjoy and relax with Netflix and other streaming included. Her eye for detail, even proving power strips next to each bed made it so easy and convenient to charge our phones. The place was spotless, clean and had updated and well stocked kitchens and bathrooms. We had everything we needed. Unfortunately, the weather didn’t cooperate for us to use the outdoor kayaks, fire pit or sitting areas, but they were beautiful as well, and added to the view from the windows. It’s conveniently located mid cape giving people access to doing various things on the cape. Walking around the neighborhood also gave us additional views of long pond. I highly recommend it, and would go back in a heartbeat. Laurie was very attentive and easy to reach. Thanks again Laurie for sharing your lovely home with us! Katie

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.

Spacious 4-Bedroom home with outdoor dining
Good location; great layout of the house; a lot of amenities; love the two sink kitchen, the pool table, and private tennis courts. Sue was very responsive and resolved any issues promptly. In our case, we took an earlier ferry (due to less traffic than anticipated traffic) so we arrived early. Sue was kindly allowed us to enter the house. This house is a rare find for our two family reunion.

Greenehill~ Up-island 1800's Vineyard farmhouse.
We stayed over the long weekend at this beautiful property. It’s located centrally close to all the major attractions and beaches. The property had beautiful features and felt very comfortable. The home itself had a lot of charm and had a positive energy. Hosts were very kind and nice to communicate with. They left us wonderful treats and fresh eggs from their beautiful garden. Overall it was a great stay at their property. Highly recommended and we will be staying there again. I will highly recommend getting a car to travel in the island so you can go to Edgartown or other places.

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!
Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking

Private Waterfront Home on Picturesque Pond
This place did not disappoint!! Beautiful location on a picture perfect pond. We enjoyed kayaking and fishing. We were only there for a weekend but I kept wishing it was for the week! The house was massive and there were plenty of beds!! Very family friendly. Games, beach gear, boats etc. all right there. If you are looking for a laid back, relaxing cape experience this is it! Fully equipped kitchen was handy for making a massive breakfast to start the day. The deck view was beautiful and the breeze was refreshing. Thank you for letting us “borrow” your home.

Ocean Oasis
Andre's place was a great experience and getaway for my family. Plenty of space, easy access to the Cape areas and Boston, and super relaxing!
Cottages with a kayak

Spectacular Beach- front home, includes linen
Our stay at Lisa's place was very pleasant. Her home is very nice with a lovely view of the lake and plenty of space for large families (we were only four people but can easily accommodate a few more). The neighborhood does not have a lot of car traffic which is great for walking and jogging around the lake. And it is also relatively close to Falmouth downtown and convenient stores. Lisa was very easy to communicate with and is very courteous and friendly. She really seems to care about her guests' comfortability. It was a pleasure dealing with her. Thank you, Lisa!

Compass Rose Cottage ★ Steps to Flax Pond & Trails
Carol is a great host. We had a small issue with the front door screen locking up and she came over right away and let us in. She is very responsive and responsible. I forgot my medication when I left and she was kind enough to mail it back to me immediately. She has a been a great host and I hope more hosts are like Carol. It rained the whole time we were there so we did not get a chance to check out the lakes around there but I am sure they are great. There is a mall near by with bowling so we did that instead. Thank you Carol for everything. Cheers

★Waterview ★Pet Friendly ★Kayaks ★Trails ★
Beautifully decorated and appointed cottage, with a cozy peaceful vibe and a view of a tranquil pond! Adorable, quiet neighbourhood! Victoria was a wonderful, helpful and responsive host. I definitely recommend this place…I had a great time. Thank you!

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
Exactly as described... And Sloane was incredibly proactive. The community had a water outage the morning we were due to check in and she contacted us immediately -- it was completely resolved before we checked in and she stayed on top of everything for us. Highly recommend visiting this cottage! Thank you, Sloane!

Kayaks and Glimpses of Westport Bay
Linlin was a wonderful host and we loved this adorable cottage. It was incredibly clean, while still being warm and welcoming for us (and our pup). It's a little farther from the water than we had anticipated, but it's a relatively short and private walk to a dock with kayaks and beautiful views. Highly recommend!

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
We had a great stay. We rented the cottage a little last minute but Leah was able to make it happen for us! You can walk down to the water which is nice, especially with kids. Very cozy. Thank you!!
Quick stats about holiday rentals with a kayak in Tisbury
Total rentals
40 properties
Nightly prices starting at
$231 AUD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Brown University
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Roger Williams Park Zoo
- Owen Park Beach
- Point Judith Country Club
- Coast Guard Beach
- Oakland Beach
- Onset Beach
- Inman Road Beach
- South Shore Beach
- Nickerson State Park
- Fort Adams State Park
- Second Beach
- Oyster Harbors Beach
- Pinehills Golf Club
- Goddard Memorial State Park