
Holiday rentals with a kayak in Chatham
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Top-rated rentals with kayak in Chatham
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House rentals with a kayak

Falmouth Summer Escape – Sleeps 6-Dog Friendly!
We have stayed at Brian’s place two years in a row, and it is by far the best airbnb we have ever stayed at. We love the amenities! Also, it is always incredibly clean and has super comfortable beds. Brian is incredibly responsive and accommodating, overall, an amazing host! We highly recommend staying here and plan to come back again!

Swan nest escape
I had high expectations coming in, but this home exceeded them by far. The interior is spotless, the condition is great, you could see that the owners put a lot of effort into it with lots of nice little touches to improve utility and aesthetics. Eugeniya was super helpful the entire time, she and Rudy are awesome hosts. I want to point out that the location is also very nice. We liked the town, the restaurants, the beach (15-20 minutes drive), Mashpee Commons. Santuit pond is wonderful and provides some nice fishing spots. The big pleasant surprise was the Santuit Pond Reserve, it’s in walking distance and provides tons of great hiking opportunities. There are many other attractions nearby, I recommend visiting Heritage Museums & Gardens in Sandwich (20 minutes away). Overall we had the best time, I highly recommend this place!

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.

25 Menemsha Rd., Popponesset, pond & beach views
Our family had a wonderful stay. The house is in a very special location, with a very short and easy walk to the beach, and right next to a pond. Our boys woke up bright and early each morning to fish in the pond and we could sit on the deck and watch them reel in some nice fish! Hot tub was a nice bonus. The neighborhood was walkable and the beach was really beautiful. Thankful to have found this house and been able to stay for a few days. Host was responsive and easy to work with!

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!

Cozy ranch with private neighborhood beach
The home was lovely. The inside and outside were just as described in the pictures. The home had everything needed in the kitchen for cooking, although we chose to order food for delivery. The neighborhood was very quiet with friendly neighbors. The location was close to groceries and shopping—great locations for the ferries (Woodhole and Island Queen) to Martha's Vineyard. Although my stay was short, the accommodations were perfect! CONS: It was most challenging to navigate the channels on the TV's in the home. I would only recommend having a local channel guide available.

Seaside Getaway - Harwichport Beachhouse
Beautiful home and just what we were looking for! Not only does this house have all the amenities you could need including a full kitchen with cookware, a fire pit and grill, but the proximity to the beach is the best. The host is responsive and gave us many reccomendafions making our stay even better. I cannot recommend this place enough!

The Blue Lagoon, Oak Bluffs
Thank you Brian we enjoyed our stay. The home is beautiful and so many amenities. The rooms are large and everything was so neat and clean. The open floor plan allowed us to sit and watch TV as well as cook in that beautiful gourmet kitchen. We will be back!
Cottage rentals 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

“Cozy Cottage” on Great Bay
Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!

Cape Escape-The Perfect Getaway
We needed somewhere to stay for a wedding down the road. Kevin’s place was more than we were expecting! It was perfect! Clean and spacious. We will be keeping this top of our list for places to stay when on the Cape!

Cottage near bay beach- 1 Bd/1Ba
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!

Beachfront at Days' Cottages! Renovated, Kayaks!
It was pricey but considering where it’s located it was worth it! Very clean and comfortable….wonderful and relaxing getaway 😎 hope to go back again.

The Lemon Drop Cottage- Swan Pond River Views!
The Lemon Drop was perfect! Just like the pictures with a clean beachy inside and amazing outdoor space. We had a wonderful time with all the amenities easily available. Great communication throughout our stay

Onset beach, Cape code.Private Waterfront cottage
We had such a peaceful and relaxing stay! The setting was incredibly serene, and we felt completely at ease the entire time. All of the amenities, especially the boats and kayaks, were very accessible, and we used them throughout our stay — it really made the experience special. We also loved spending cozy nights around the campfire, which added such a warm and memorable touch. There was so much for the kids to do, and they had a fantastic time as well! The host was so kind and welcoming, and communication was very easy from start to finish. Everything was thoughtfully prepared, and it made for a truly wonderful getaway. Highly recommend for anyone looking for a quiet, fun, and family-friendly escape!
Quick stats about holiday rentals with a kayak in Chatham
Total rentals
20 properties
Nightly prices starting at
₹6,857 before taxes and fees
Total number of reviews
550 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- New Silver Beach
- Onset Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Inman Road Beach
- Kalmus Park Beach
- Ridgevale Beach
- Cahoon Hollow Beach
- Grey's Beach
- Grays Beach
- Forest Beach
- Lighthouse Beach