Vacation rentals with a kayak in Massachusetts

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Massachusetts

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Dennis

4.96 out of 5 average rating, 113 reviews

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

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this quintessential beach rental featuring: Private hot tub & patio in a peaceful backyard, 55” Sony TV w/ apps, indoor gas fireplace🔥 ductless splits, 2 kayaks, outdoor shower, games, washer/dryer, comfy furnishings, stocked kitchen & gas grill. Relax & watch the birds enjoying their bath & feeders, hang out back in peace & privacy or go out & explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation! ➡️Bayside_Retreat_Capecod

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

Condo Duplex only 2/10 of a mile to Paines Creek Beach on Cape Cod Bay; great for sunsets. SAT TO SAT WEEKLY ONLY JUN-SEPT SEASON. 1 bedroom w/ wall A/C, one bath with living room/ kitchen area, enclosed porch with futon provides additional sleeping area. Patio out the back door awning w/ gas grill private wooded yard, use of tandem kayak (2 life jackets) at tenants own risk. Nearby donut shop, liquor store and seafood/ice cream stand. NO Pets Accepted. 3-day minimum during off-season (Oct-Apr)

Top guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 104 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Superhost

A charming lake house is positioned by the water, featuring a quaint peaked roof and large front windows that bring in natural light. A porch offers seating, while a grill is visible to the left. Surrounding greenery enhances the tranquil setting.

Home in Westminster

4.82 out of 5 average rating, 152 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Guest favorite

Place to stay in Dartmouth

4.88 out of 5 average rating, 33 reviews

No Egrets Haven-Oceanfront Retreat

Entire home with complete privacy! Unforgettable memories start here! Nestled at the end of a quiet dead-end street, this home offers peaceful sunsets by the fire pit, kayaking from the dock, and cornhole with family and friends. Walk to the village for shopping and dining. Conveniently close to Providence, Boston, and Newport, with easy trips to Cape Cod, Martha’s Vineyard, Nantucket, and Block Island. Enjoy a winery tour, a day of boating, or simply relax in this stunning coastal retreat!

Superhost

A vibrant yellow kayak is seen on calm water, with a child paddling and smiling. A floating dock is partially visible nearby, with trees lining the shore in the background under a clear blue sky. Gentle ripples reflect the sunlight, creating a serene atmosphere.

Cottage in Wareham

4.86 out of 5 average rating, 148 reviews

Onset beach, Cape code.Private Waterfront cottage

PRIVATE LAKE FOR YOUR Vacations year around. Spend quality time on spectaculars Blackmore pond.Comfortable cottage,step away from the water.Your own big dock out of your house as you wake up .Enjoy sunshine and sunset during summer , beautiful foliage , experience the ice or Snow drop during winter. this is exceptional romantic for your family . Well located next Onset beach, Water Park , Water Wizz of Cape Code. , Gate to Cape , To Ferry to Nantucket, Martha vineyard, Plymouth to P-Town

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, 468 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Guest favorite

Home in Mashpee

4.92 out of 5 average rating, 136 reviews

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

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Guest favorite

Cottage in Falmouth

4.93 out of 5 average rating, 169 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

Guest favorite

Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.

Cottage in Westport

4.9 out of 5 average rating, 105 reviews

Kayaks and Glimpses of Westport Bay

Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

Top guest favorite

A cozy outdoor seating area includes four chairs with blue cushions surrounding a gas fire pit. The space is bordered by trees and overlooks a tranquil pond, providing a pleasant setting for relaxation.

Home in Yarmouth

5 out of 5 average rating, 304 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

Top guest favorite

A table with multiple seating options overlooks a serene waterfront view through a screened area. Lush greenery surrounds the landscape, with a clear sky above and water reflecting natural light in the distance. The outdoor space offers a sense of tranquility and connection with nature.

Home in Dennis

4.96 out of 5 average rating, 193 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.