Vacation rentals with a kayak in Massachusetts

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Popular amenities for Massachusetts kayak rentals

House rentals with a kayak

Top guest favorite
A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.
Home in Yarmouth
5 out of 5 average rating, 306 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

ThanhRating, 5 stars1 week ago
10/10 stay!! The cottage sits on a beautiful pond. We came during a rainy weekend so we stayed mainly inside. We turned on the electric fireplace & put on a movie. It was so cozy. Once the rain let up, we went outside and used the outdoor fireplace! So peaceful. Everything else you’d need, you are only a short drive from a cvs & grocery store. Melissa is a great host. We really appreciate how quick she responded with any minor concern we had. We look forward to more future stays at the cottage!
Superhost
The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.
Home in Yarmouth
4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

JennaRating, 5 stars9 months ago
The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.
Guest favorite
Several colorful kayaks are lined up on a grassy area near a tranquil lake. A wooden dock extends into the water, surrounded by lush trees. A park bench offers a comfortable spot to relax and enjoy the serene natural setting.
Home in Becket
4.94 out of 5 average rating, 148 reviews

Lake front retreat - Stylish Berkshire home

BetsyRating, 5 stars1 month ago
We had a wonderful long weekend at Elle’s house. The bedrooms and living spaces were thoughtfully laid out and decorated beautifully. A short drive to lots of little cafés and hiking trails. We appreciated the quiet solitude of this little getaway in the Berkshires, and the ping pong table too. We didn’t get to use the lake (snow in April!) but hope to return to try again!
Guest favorite
A spacious deck features a glass-top table and a blue Adirondack chair overlooking the river. The warm glow of the sunset reflects off the water while trees provide a serene backdrop, creating a peaceful outdoor space.
Home in Westport
4.96 out of 5 average rating, 28 reviews

Riverhouse

WendyRating, 5 stars4 months ago
This was the perfect place for three friends who write and workshop together online to gather in person. The main room of the house is filled with light and what I didn't realize from the listing is the beautiful view from the living/dining room down to the river. The kitchen is well supplied and every room was very clean and uncluttered. The three bedrooms on the first floor are all very nice, with good beds and pillows (one is slightly larger with a king-sized bed), so we were able to decide on our rooms painlessly and none of us had to settle for an inferior room. The large dining table was perfect for spreading out our work as well as for dining, and one of us enjoyed having the furnished basement as her private work space. When we had a problem with hearing a beeping noise, which we initially thought might be a smoke detector battery that needed replacing, Bob was very responsive and helpful in figuring out the cause of the beeping from a motion detector. We plan to come again.
Superhost
A bright yellow kayak rests on the sandy shore, partially surrounded by lush green grass. Calm waters stretch towards the horizon, reflecting the blue sky and distant tree line. Gentle waves lap at the shoreline, creating a peaceful scene by the water's edge.
Home in Eastham
4.81 out of 5 average rating, 110 reviews

Cute Cottage Living by the Sea!

CoriRating, 5 stars3 weeks ago
It was better than what was advertised! We’d definitely stay again.
Guest favorite
An open living area features natural wood flooring and soft blue walls. A round dining table sits beside a cozy seating arrangement, creating an inviting space. Large windows enhance natural light, and a modern kitchen area is visible in the background.
Home in Mashpee
4.92 out of 5 average rating, 141 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

MarilinRating, 5 stars1 week ago
Kristen’s place was really nice went there with my adult daughters for a weekend getaway Kristen was an awesome host she reached out to me a couple of days before our day to arrive just to let me know that we were able to check in before three and on our last day reached out to tell us that if we need more time we could stay later she’s amazing would definitely be back and we highly recommend this place!!!
Guest favorite
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars7 months ago
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!
Guest favorite
An open-concept living area features a comfortable sectional sofa, wooden coffee table, and bright skylights allowing natural light to fill the space. A modern kitchen with a large island and bar seating complements the airy atmosphere, providing a seamless flow to the dining area and views outside.
Home in Otis
4.96 out of 5 average rating, 110 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

ChrisRating, 5 stars2 weeks ago
Adam's place was the perfect location for our annual spring fishing trip. Plenty of space for everyone to relax their own way let still be connected to the group. Kitchen is well equipped for anything you would want to cook with other extras like coffee maker and blender. It's a short walk to the docks which makes fishing for a full day convenient to take breaks / have lunch etc. The boathouse is a nice added amenity which allows storage of coolers, drinks and ice which is also very close proximity to the fire pit. We are already looking forward to next year's trip.

Cottage rentals with a kayak

Top guest favorite
The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.
Cottage in Dennis
4.94 out of 5 average rating, 115 reviews

Compass Rose Cottage ★ Steps to Flax Pond & Trails

JohnRating, 5 stars2 weeks ago
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
Guest favorite
A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.
Cottage in Yarmouth
4.92 out of 5 average rating, 473 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

ConstanceRating, 5 stars4 days ago
One of the best getaways we've had so far. The location was nicely situated away from the crowds and the traffic. The neighborhood is very quiet. 2 rabbits reside somewhere on the property. They came to visit every morning and evening. We enjoyed feeding them strawberries. We used the bikes which were maintained very well. You may want to bring a car that can handle packing up the kayaks. Water access is not walkable. But, you can ride bikes to restaurants, shops, and market. We loved the space. Perfect size for a couple. The kitchen had everything we needed. We ordered groceries from Shaws. Saved a lot of money cooking and eating in most nights.
Top guest favorite
Cottage in Yarmouth
5 out of 5 average rating, 218 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

MaryRating, 5 stars1 week ago
Serenity Cottage was the perfect location for a family getaway. The house is bright, clean and extremely comfortable. It had every amenity we could possibly need for our family of two adults, one toddler and one infant. We immediately felt at home. Lee Ann was a perfect host. All instructions and communications were clear and easy to follow. She was proactive to reach out during our stay and gave us great recommendations. The setting was truly stunning and allowed us to enjoy Cape Cod with ease. The cottage is in a great location - within driving distance of beaches, shops, and restaurants. Thank you, Lee Ann! We will absolutely be back to Serenity Cottage.
Guest favorite
Cottage in Falmouth
4.94 out of 5 average rating, 170 reviews

“Cozy Cottage” on Great Bay

AngelaRating, 5 stars1 month ago
Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!
Guest favorite
Cottage in Dennis
4.97 out of 5 average rating, 115 reviews

Local Beach+ Fireplace + Hot Tub Under the *Stars*

LeilaRating, 5 stars3 weeks ago
Had a wonderful time celebrating my wife’s birthday there!! The place is super cozy and cute and the hot tub is perfect! Christina the host made sure everything was clean and spotless for us plus the house had a guide with instructions about the place e recommendations about what was around… we will definitely come back soon! 2 days in paradise was not enough!
Superhost
The exterior of the condo duplex is showcased, featuring a shingle-style façade, a welcoming porch with a white door, and large windows. Lush greenery, including shrubs and a small tree, surrounds the entrance, enhancing the inviting appearance of the property.
Cottage in Brewster
4.82 out of 5 average rating, 11 reviews

Cottage near bay beach- 1 Bd/1Ba

GraceRating, 5 stars7 months ago
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars8 months ago
My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.
Guest favorite
The spacious deck is softly illuminated by string lights during the evening, creating a cozy atmosphere. Seating areas are arranged around a fire table, with surrounding greenery and potted plants enhancing the outdoor setting. A nearby building is partially visible in the background.
Cottage in Dennis
4.95 out of 5 average rating, 100 reviews

The Lemon Drop Cottage- Swan Pond River Views!

HeatherRating, 5 stars9 months ago
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

Cabin rentals with a kayak

Top guest favorite
A cozy sunroom features two spacious daybeds adorned with soft blankets and cushions, positioned beside large windows that offer serene views of the pond. Natural light floods the room, highlighting wooden walls and a unique stained glass window at the peak of the ceiling.
Cabin in Athol
4.97 out of 5 average rating, 73 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

AimeeRating, 5 stars1 day ago
If you’re looking for a peaceful and relaxing environment, this place was perfect. Between the hammock, the soaking tub, and the view of the water - especially from the gorgeous and cozy sunroom - it was exactly what I needed. Also, WiFi signal was actually pretty decent!
Top guest favorite
A view of the cabin and neighboring house is presented, surrounded by trees. The yard is partially covered with fallen leaves, revealing patches of green grass. A gravel driveway leads towards the entrance, providing access to the property.
Cabin in Webster
4.93 out of 5 average rating, 166 reviews

The Camp

TorRating, 5 stars1 week ago
We truly enjoyed our stay at Karin’s place. She is a gracious host. There were great cottage offers beautiful lake experiences, including beautiful sunsets. She has a great waterfront and an expansive yard. It’s located on the Massachusetts, Connecticut and Rhode Island border with easy access to 3 states.
Guest favorite
A log cabin is surrounded by tall trees and lush greenery, situated on the shore of a tranquil lake. A wooden dock extends into the lake, with two kayaks and a rowboat visible nearby, offering a serene setting for relaxation.
Cabin in Groton
4.93 out of 5 average rating, 29 reviews

Secluded Rustic Lakeside Cabin - Perfect Escape

CharlesRating, 5 stars5 days ago
What a wonderful place to spend a few days. Peaceful serene and absolutely beautiful. The place is spotless and comfortable. Eric and Irie are tremendous hosts always willing to go the extra mile for our comfort. I would highly recommend this beautiful cabin on the lake!!
Guest favorite
The exterior of a contemporary wooden home is presented, highlighted by large window features and a distinctive A-frame roof. Surrounding greenery includes a well-maintained lawn and various shrubs, creating a natural setting. A garage is visible to the left, providing easy access.
Cabin in Becket
4.86 out of 5 average rating, 112 reviews

Wildlife Retreat in the Forest

DiegoRating, 5 stars1 month ago
The place was great. Very private and the deck is a lovely and spacious. The living room is huge, beautiful, and great for a big group to hang out in. Things were clean and it had everything we needed.
Guest favorite
A round wooden dining table is accompanied by four light-colored chairs, positioned near large windows. The views of lush greenery and the lake are visible through the windows, creating a bright and inviting space.
Cabin in Douglas
4.9 out of 5 average rating, 10 reviews

Rustic Log Cabin on the Lake

RobertRating, 5 stars2 weeks ago
Ethan’s place is in a great area. It’s an awesome get away. Highly recommend.
Guest favorite
Cabin in Winchendon
4.96 out of 5 average rating, 47 reviews

The little house on Mirror Pond

SandraRating, 5 stars1 week ago
Michelle was an exceptional host and her little cottage was in amazingly beautiful place to be. The inside was impeccably clean, and decorated with a simple elegance. She had so many lovely touches, such as quality shampoo and soaps; Q-tips and cotton balls and hairbands available; even the best toilet paper lol!! The kitchen was equipped with every possible thing you could use, and when we couldn’t locate a blender, Michelle went out and got a brand new one and delivered it that day… which we told her she did not have to do!! If this place allowed tiny dogs, I would see if I could rent it for a whole month in the summer…Even though the weather was cool and rainy and we didn’t get to enjoy the lake, we felt nourished by the sweetness of the inside space with the beautiful window views of the lake and woods. Please do yourself a favor and go to Michelle‘s place.
Superhost
A wooden dock extends into a calm lake, featuring two red Adirondack chairs facing the water. A large float is positioned nearby, with trees lining the opposite shore under a partly cloudy sky.
Cabin in Otis
4.87 out of 5 average rating, 54 reviews

Enjoy 43 Acres on Two Ponds!

PatrickRating, 5 stars2 weeks ago
We had a great stay for my daughter’s college graduation. Really enjoyed the house and fire pit. Thanks!
Superhost
A cozy fire pit area is surrounded by multiple wooden chairs, inviting relaxation. The serene lake reflects the surrounding trees and colorful autumn foliage, adding to the peaceful setting. The lush green grass blends effortlessly with the natural landscape.
Cabin in Otis
5 out of 5 average rating, 4 reviews

Berkshires Lakefront Boho Modern Retreat

MelissaRating, 5 stars3 months ago
What a beautiful home in a gorgeous setting. We unfortunately got caught in a winter storm during our stay. Christina went above and beyond to make sure we were taken care of during the inclement weather. We will definitely stay here again!

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