
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

Private beach
We had an amazing time in Tracy’s home. The view from the garden is breathtaking and the kids loved playing on the beach and enjoyed canoeing and paddling on Pleasant Bay. We will come back!

Lake charm
We had a wonderful long weekend! The home was beautiful, clean and peaceful! Excellent communication! We could not have asked for more!!!

Oceanfront | Firepit | Gameroom | Pets | Kayaks
Amazing host! Great communication and hospitality. We had a great time and will be back.

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!

NEW! Water Views + Dog Friendly Cape Cod Retreat
Quiet neighborhood and lovely sitting out on the deck with the sounds of nature. The property was well appointed inside with everything working as it should and well maintained.

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!!!

Escape to cape/water front home
We had a wonderful stay at the house. The kitchen was very well equipped, the bathrooms were pristine and the bedrooms were super comfortable. Tam was always very responsive to questions and provided useful details that helped make our trip fun. We would happily stay at the house again, and we plan to!

Waterfront, Kayaks, Paddle board, Fire Pit
We particularly enjoyed sitting by the pond and on the deck, where you feel like you're in a treehouse... The flowering plants on the deck are a lovely touch, as well as the hydrangeas, peonies, roses and meditating frog surrounding the firepit. If both people sharing a room like to read books in bed, note that only one side of the bed is equipped with a light, so bring a booklight! Michelle was easy to contact, and we appreciated the recommendations for local beaches and eats.
Cottage rentals with a kayak

Spectacular Beach- front home, includes linen
We had a wonderful time at the lake house. So very relaxing and peaceful. The view from the deck was so beautiful. Lisa was a great communicator as well. The house location is great because it's so close to the Ferry if you'd like to head to Martha's Vineyard for the day and close to some great little restaurants and shops in town.

Compass Rose Cottage ★ Steps to Flax Pond & Trails
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.

“Cozy Cottage” on Great Bay
we had a lovely relaxing vacation - we stayed for almost 2 weeks. The cottage was just as pictured and described - delightful and comfortable. Outdoor space was excellent with many seating areas so we could choose sun or shade or a partial shade all hours of the day. It was very useful having a washer and dryer during our stay, too. The kitchen was well equipped and worked great for us. The neighborhood was quiet and private. Doug and Robin were very responsive, not that we had any issues! We just wanted to know garbage and recycling days!! Wifi and TV were excellent. We highly recommend this cozy cottage and we would definitely come back!

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
I cannot say enough good things about Felicia‘s little Boho Retreat by the Beach. The place was immaculate, and her attention to detail and decor was spot on. Lovely, soft on your skin linens, beautiful view of the beach side park on the river, a well supplied kitchen for all your cooking needs including tools, extra spices, coffee, tea, etc. a welcome card with snacks and a flower to greet you on the center island. It made you feel like a good friend was welcoming you into their home. The surroundings are lovely. We enjoyed sitting on the patio for a good read or a nap and there are kayaks at the side of the house that we used for a lovely paddle one morning. If you are looking for a great getaway with a spouse, friend or sibling, this is the place to go.

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!
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.

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
$102 SGD 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
- Coast Guard Beach
- Sandwich Glass Museum
- Owen Park Beach
- Nickerson State Park
- Onset Beach
- Oyster Harbors Beach
- Inman Road Beach
- White Horse Beach
- Pinehills Golf Club
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Forest Beach
- Corporation Beach
- Linnell Landing Beach
- Cape Cod National Seashore
- Lighthouse Beach
- Ellis Landing Beach