
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

impeccable cottage STEPS to downtown OB & beach!
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!

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!

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.

Freshwater Cottage - 1 min walk to private beach
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!

Oceanfront | Firepit | Gameroom | Pets | Kayaks
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!!!
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
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 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!

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.

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
$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
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Coast Guard Beach
- Owen Park Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- Oyster Harbors Beach
- White Horse Beach
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Scusset Beach
- Forest Beach
- Lighthouse Beach
- Corporation Beach
- Linnell Landing Beach