Holiday rentals with a kayak in Chatham

Find and book unique kayak rentals on Airbnb

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Popular amenities for Chatham kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
Home in Oak Bluffs
4.92 out of 5 average rating, 174 reviews

impeccable cottage STEPS to downtown OB & beach!

SophiaRating, 5 stars2 weeks ago
My family and I had a lovely stay in Oak Bluffs, MA! We loved walking around town (which is only a few minutes away on foot) and spending our time relaxing in the cottage after exploring. There are great restaurants, local shops, and beautiful scenery all within walking distance. Even though we brought our car (which was great for traveling to the island), we practically didn't need it to get around. Brianna was very responsive and accommodating during our stay. We appreciated her willingness to answer any questions and enjoyed our stay. We would love to come back!
Guest favourite
Home in Mattapoisett
4.9 out of 5 average rating, 10 reviews

Buzzard Bay Getaway

AnnaRating, 5 stars9 months ago
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.
Guest favourite
Home in Mashpee
5 out of 5 average rating, 9 reviews

Swan nest escape

VadimRating, 5 stars9 months ago
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!
Top Guest favourite
Home in Barnstable
4.98 out of 5 average rating, 42 reviews

Private Lake Beach | Spectacular Views & Amenities

AndrewRating, 5 stars2 months ago
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.
Guest favourite
Home in Plymouth
4.97 out of 5 average rating, 64 reviews

Freshwater Cottage - 1 min walk to private beach

NicoleRating, 5 stars1 month ago
The cutest house! Well designed, super clean, and COZY. We especially enjoyed the fire pit! After a night out for my 40th birthday it is was the perfect ending. Highly recommend for anyone traveling to Plymouth area!
Top Guest favourite
Home in Buzzards Bay
4.96 out of 5 average rating, 47 reviews

Oceanfront | Firepit | Gameroom | Pets | Kayaks

BenRating, 5 stars2 weeks ago
Lovely spot near end of a cul de sac, great water views and light. Joel was proactive and responsive in communication.
Top Guest favourite
Home in Mashpee
5 out of 5 average rating, 10 reviews

Escape to cape/water front home

BrendanRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Barnstable
4.97 out of 5 average rating, 38 reviews

Cozy ranch with private neighborhood beach

NicoleRating, 5 stars4 days ago
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!!!

Cottages with a kayak

Guest favourite
Cottage in Falmouth
4.86 out of 5 average rating, 108 reviews

Spectacular Beach- front home, includes linen

LeticiaRating, 5 stars1 month ago
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!
Top Guest favourite
Cottage in Dennis
4.94 out of 5 average rating, 117 reviews

Compass Rose Cottage ★ Steps to Flax Pond & Trails

SharonRating, 5 stars1 week ago
The cottage is the essence of Cape Cod. Beautifully maintained and isn't misssing a thing. Absolutely loved the cottage, it brought me back to my childhood when we stayed in a similiar cottage on the beach.
Guest favourite
Cottage in East Falmouth
4.94 out of 5 average rating, 171 reviews

“Cozy Cottage” on Great Bay

JessicaRating, 5 stars2 weeks ago
We had a lovely time spending our weekend here! It was cozy, comfortable, and a super memorable trip!
Superhost
Cottage in Dennis Port
4.92 out of 5 average rating, 130 reviews

Cape Escape-The Perfect Getaway

KearraRating, 5 stars1 week ago
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!
Superhost
Cottage in Brewster
4.82 out of 5 average rating, 11 reviews

Cottage near bay beach- 1 Bd/1Ba

GraceRating, 5 stars8 months ago
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!
Guest favourite
Cottage in North Truro
4.98 out of 5 average rating, 89 reviews

Beachfront at Days' Cottages! Renovated, Kayaks!

ColleenRating, 5 stars4 days ago
Great stay in Truro with friends for a girl weekend. The cottage is clean, cute and had the basic necessities for a weekend. The location can’t be beat being right on the beach and we loved it! We had 4 people in the cottage and it is quite tight. The two full beds are up against walls so while you can sleep 2, you’d need to climb over the other to get out. Getting ready was challenging with the mirrors in very tight quarters in the bathroom and bedroom and not a lot of room to put your things. The sofa in the living room was really comfy and nice to wake up to views. Overall, great spot and stay but would likely opt for a hotel in the future to get more value for what we paid in terms of space and overall comfort. We did know the cottage was small going in so no regrets there.
Top Guest favourite
Cottage in Brewster
5 out of 5 average rating, 12 reviews

Modern Cottage on 6 Acres -Walk to Beach and 6A!

RichardRating, 5 stars6 days ago
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!
Superhost
Cottage in Wareham
4.86 out of 5 average rating, 152 reviews

Onset beach, Cape code.Private Waterfront cottage

JoannaRating, 5 stars1 month ago
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

    $123 AUD 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

Destinations to explore