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

Buzzard Bay Getaway
While the weather did not cooperate (it rained the entire time) the cottage and views made up for the weather. From the table to the couch the views are wonderful. The cottage is very well stocked from towels and blankets to the kitchen. We did not need anything that wasn't supplied. The bathroom is small but functional. The shower might not work well for a larger person. The neighborhood is quiet and feels very safe and peaceful. We enjoyed our long weekend and would book this cottage 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!

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.

Oceanfront | Firepit | Gameroom | Pets | King Bed
Lovely spot near end of a cul de sac, great water views and light. Joel was proactive and responsive in communication.

Escape to cape/water front home
The house and Tam were fantastic! Tam's attention to detail in both the house and how it was prepared for us made it super easy and stress-free to get settled. We had an amazing time!

Cozy ranch with private neighborhood beach
We had a family wedding and needed a home where we would be comfortable to stay and get ready. I found this home and so glad I did - we hit the jackpot! Although, due to our busy weekend schedule, we did not get to take advantage of all of the amenities this house has to offer, I would recommend it to anyone looking for a comfortable, newly updated and very clean home! The location for us was just perfect and with the gorgeous backyard and patio, we did enjoy every minute we were there! As someone who also owns rental property, I can tell you the communication was amazing and so appreciated, and those welcome snacks were just what we needed after a long drive! Thank you, Lauren!!!

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!
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!

“Cozy Cottage” on Great Bay
We had a lovely time spending our weekend here! It was cozy, comfortable, and a super memorable trip!

Cape Escape-The Perfect Getaway
Our stay at Kevin’s cottage was nothing short of amazing! He had everything we needed to make our stay the best, even things you wouldn’t think an Airbnb would have which was sooo helpful! Very clean, the location was in the middle of all the things we wanted to do while at the cape, and just overall a cute little cottage. Loved the outside shower as well!! Kevin was also so helpful with everything and a great host. Couldn’t recommend enough! We’ll be back!

Little Boho Retreat by the Beach
Felicia and Little Boho Retreat by the Beach deserve all the raving reviews. In all honesty I wish I could give more than five stars. The cottage is cozy, well-stocked, and every attention to detail is notable. Felicia thought of everything. The cottage is a destination in and of itself, to say nothing of the wonderful places we visited on The Cape, as well as Plymouth, Wareham, and Marion. I feel like there is so much more to do and experience on Dexter Beach and in this area. We definitely would like to return to this spot.

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!
The stay at Larkspur was nothing short of fantastic. The cottage was very clean and well maintained. My wife and I had the privilege of having our honeymoon here and I would recommend it to everyone. We can't wait to come back with our future family!

Modern Cottage on 6 Acres -Walk to Beach and 6A!
This place was absolutely amazing! Nice and private but conveniently located. The house was very comfortable and had all the amenities you need. Close to the beach and all the best spots in Brewster. My son’s favorite part was Basil the dog, who would come greet us as we hiked the expansive property. Would highly recommend and would stay here again in the future!

Onset beach, Cape code.Private Waterfront cottage
Cute spot! Loved the ease to the water! Got in first night and they even had the light on for us. Close to anything you need!! Perfect for a Mother’s Day get anyway for me and my three girls! Fished/boated/swam and had a great time! Van was willing to accommodate a late check out for. Decent price, although we ended up heading out on time I was grateful for this! Can’t wait to go back! Thanks Van and Family!!!
Quick stats about holiday rentals with a kayak in Chatham
Total rentals
20 properties
Nightly prices starting at
$133 NZD 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
Wi-Fi availability
20 properties include access to Wi-Fi
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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
- Onset Beach
- Inman Road Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Kalmus Park Beach
- White Horse Beach
- Cape Cod National Seashore
- Forest Beach
- Linnell Landing Beach
- Ridgevale Beach
- New Silver Beach