Vacation rentals with a kayak in Brewster

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Popular amenities for Brewster kayak rentals

House rentals with a kayak

Guest favorite
An outdoor space featuring a fire pit surrounded by Adirondack chairs, set on a grassy area. In the background, a two-story house is visible with a staircase leading to the second floor deck, nestled among trees.
Home in South Yarmouth
5 out of 5 average rating, 12 reviews

Spacious Mid-Cape Home 5 Bedrooms, 9 Beds, 3 Bath

HannahRating, 5 stars6 months ago
We absolutely loved our stay at Rachel’s! We kept saying “this place has everything”. It was a wonderful home for a multi generation holiday hang. From a 7 month old to great grand parents. The main floor was easily accessible for family member with a disability. We felt right at home with our 7 month old, the home had a pack n play - all set up with fresh sheets, baby bath tub, high chair, bath toys, monitor, etc. The basement was perfect for the teenagers to hangout and have their space. The backyard was peaceful and extended the hang area. Rachel was incredibly friendly and responsive.
Guest favorite
Home in Dennis Port
5 out of 5 average rating, 7 reviews

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

BarbaraRating, 5 stars7 months ago
Great spot to stay in Dennis. Quiet street , easy to get everywhere. The home was comfortable, very clean and fenced in yard was lovely. Amy was kind and communicative. Would love to stay here again next time we're back in the area.
Guest favorite
An aerial view of a coastal ranch home is presented, showcasing a large green yard bordered by trees. The house features a well-maintained exterior and a patio area with seating. Nearby properties and a paved road contribute to the serene neighborhood atmosphere.
Home in Popponesset
4.95 out of 5 average rating, 21 reviews

25 Menemsha Rd., Popponesset, pond & beach views

CelesteRating, 5 stars2 weeks ago
Our family had a wonderful stay. The house is in a very special location, with a very short and easy walk to the beach, and right next to a pond. Our boys woke up bright and early each morning to fish in the pond and we could sit on the deck and watch them reel in some nice fish! Hot tub was a nice bonus. The neighborhood was walkable and the beach was really beautiful. Thankful to have found this house and been able to stay for a few days. Host was responsive and easy to work with!
Guest favorite
A bright living room features a white sofa with decorative cushions, arranged near a rustic coffee table. A cozy armchair and an ottoman are positioned nearby. Large windows allow natural light, while a fireplace adds warmth. Green plants enrich the space with a touch of nature.
Home in Barnstable
4.97 out of 5 average rating, 37 reviews

Cozy ranch with private neighborhood beach

AngelaRating, 5 stars1 week ago
The home was lovely. The inside and outside were just as described in the pictures. The home had everything needed in the kitchen for cooking, although we chose to order food for delivery. The neighborhood was very quiet with friendly neighbors. The location was close to groceries and shopping—great locations for the ferries (Woodhole and Island Queen) to Martha's Vineyard. Although my stay was short, the accommodations were perfect! CONS: It was most challenging to navigate the channels on the TV's in the home. I would only recommend having a local channel guide available.
Superhost
A spacious living area features a light-colored sectional sofa accented with blue pillows. A glass coffee table sits atop a stylish rug, with a floral arrangement at its center. Large windows allow natural light to fill the room, complemented by high ceilings and a contemporary staircase.
Home in South Chatham
5 out of 5 average rating, 9 reviews

Remodeled Cape Cod Getaway in Chatham

TimRating, 5 stars9 months ago
Me and my wife had never been to the cape and we both turned 60 so we wanted to do something we have never did before. We decided to give Cape Cod a try. i went with very low expectations . Boy was i wrong. We had no idea if Chatham was the right place to stay or not. We randomly picked this house and we are so happy we did. it was is in a nice location close to the beaches and also close to the restaurants and shopping. What a great way to celebrate our 60th birthdays. i’m d reccomend this house to anyone looking for a great location with hosts who are easy to get a hold of and a very clean well kept place. Thanks Karen and Sharon
Top guest favorite
A serene view of a freshwater pond is captured, with gentle ripples reflecting the clear blue sky. Leafless trees frame the scene, adding a touch of nature's beauty. Lush greenery can be seen in the distance, showcasing the peaceful surroundings.
Home in Eastham
4.97 out of 5 average rating, 29 reviews

Cozy Cape Stay! bike path, beaches, water view!

SophiaRating, 5 stars2 weeks ago
Jennifer is a great host! She was very responsive and very helpful about giving local recommendations. The house itself was very nice -- the redone bathrooms and kitchen were a big plus, but the house still had a lot of character. We also really enjoyed the yard space and the extra amenities such as the grill and bicycles! The only thing that could have made it better would have been if we were a bit closer to the beach, but the house itself made it worth it.
Top guest favorite
A spacious living area is presented with a large white sectional sofa, arranged around a wooden coffee table. Natural light enters through the large window, which is framed by light curtains, revealing a view of greenery outside. A relaxed atmosphere is created by the warm tones of the woven decor.
Home in South Yarmouth
5 out of 5 average rating, 24 reviews

Cape Cod Retreat

LizRating, 5 stars9 months ago
Fantastic home that clearly is actually enjoyed by the owners (so no weird surprises like you find in places that only exist as rentals). Well designed space that’s very comfortable to exist in. About a mile to the nearest ocean beach so we ended up driving more than walking but there’s plenty to do with a car.
Guest favorite
An aerial view captures the layout of the property, featuring two houses connected by a spacious driveway. Lush greenery surrounds the homes, with blooming azaleas in vibrant colors near the entrance. The backyard is expansive and well-maintained, providing a sense of seclusion.
Home in Chatham
4.96 out of 5 average rating, 57 reviews

2 House Compound, Huge Yard, Game Room, Kayaks

ChristinaRating, 5 stars1 week ago
This house was beautiful! We had an amazing time with our family of ten. We had so much space between the main house and carriage house. Both houses are very clean and spacious and the beautiful yard was big enough to play family kickball and wiffle ball games. We also played Bocce ball and cornhole, which were both available in the garage. The house is in a peaceful neighborhood and just minutes from downtown Chatham, beaches, restaurants, and more. Jackknife Beach was just down the road and the kids had a great time playing in the water and building sandcastles. Also, just 50 minutes to Provincetown. Katie was very responsive to all our questions and had great recommendations. The house had everything we needed and more with a fully stocked kitchen. The carriage house is so much bigger than we expected with a full kitchen and its own washer and dryer. Perfect for large families. We had the Best vacation and made so many memories here. Definitely recommend and would love to come back!

Cottage rentals with a kayak

Top guest favorite
A well-maintained pathway leads to a serene cottage entrance, flanked by lush greenery and landscaped beds. A stone water feature creates a calming ambiance, while lounge chairs are positioned nearby for relaxation. Sunlight filters through the trees, enhancing the tranquil outdoor setting.
Cottage in North Eastham
5 out of 5 average rating, 39 reviews

Cape Cottage Escape

DanaRating, 5 stars1 week ago
Amazing and peaceful stay! Can’t recommend this place enough and the hosts! We had the best honeymoon. :)
Superhost
An aerial view showcases the Cape Cod beach house nestled in a lush green landscape. The surrounding neighborhood features various homes set among trees, with views of nearby water and serene pathways visible in the distance.
Cottage in Hyannis Port
4.81 out of 5 average rating, 31 reviews

Beach house- walk to ocean + 2 min to Craigville

JillianRating, 5 stars10 months ago
Our family had a wonderful time in Barnstable! Lynn and Ken were extremely responsive and did a great job at communicating when needed. The house was perfect for our family of three. Everything was clean and appeared exactly as the photos presented. We loved spending time on the screened in porch and the outdoor shower was a plus. Being less than 5 minutes from Craigville Beach was ideal along with the use of the beach pass. We would recommend this listing to anyone without hesitation and hope to book again for a future stay!
Guest favorite
Cottage in East 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!
Superhost
A charming Cape cottage is framed by lush greenery, with sections of neatly mulched garden beds featuring flowering plants. An American flag hangs at the entrance, complemented by a stone walkway leading to the front door. The property is bathed in natural sunlight.
Cottage in Dennis Port
4.92 out of 5 average rating, 130 reviews

Cape Escape-The Perfect Getaway

KearraRating, 5 stars4 days 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!
Guest favorite
A circular seating area contains five Adirondack chairs in various colors, arranged around a firepit. The space is surrounded by trees, with a view of the lake visible in the background, providing a serene outdoor spot for relaxation.
Cottage in Harwich
4.85 out of 5 average rating, 26 reviews

Lakeside Waterfront House in Harwich: 4+beds, 3bth

ColinRating, 5 stars6 days ago
Absolutely amazing house, fit all of us comfortably and a great host. Art was there to respond to all of our questions and was responsive and extremely helpful .
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 stars8 months ago
Cute little cottage, looks just like the photos. Walking distance to beach and walking trails!
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 Port
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
Top guest favorite
The cottage exterior is showcased, featuring a charming purple façade with black shutters. A landscaped yard with a gravel pathway leads to a private deck area. Surrounding greenery includes trees and shrubs, creating a tranquil outdoor setting.
Cottage in Brewster
5 out of 5 average rating, 12 reviews

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

RichardRating, 5 stars2 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!

Quick stats about vacation rentals with a kayak in Brewster

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    1K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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