Vacation rentals with a kayak in Middlesex County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Middlesex County

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

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Top guest favorite
Cabin in Groton
4.94 out of 5 average rating, 63 reviews

Secluded Rustic Lakeside Cabin - Perfect Escape

Take it easy at this unique and tranquil getaway. Escape to our log cabin nestled in the heart of the woods and perched on the serene shores of a pristine lake in Groton, Massachusetts, less than 1 hr from Boston. This secluded hideaway offers the perfect blend of rustic charm and modern comfort, providing an idyllic setting for a tranquil getaway. Our cabin ensures complete privacy and a true sense of escape. Enjoy uninterrupted views of the sparkling lake and the soothing sounds of nature.

Superhost
Home in Westminster
4.88 out of 5 average rating, 211 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Guest favorite
The exterior of a charming colonial-style townhouse is shown, framed by vibrant autumn foliage. A well-maintained front yard with manicured grass and decorative bushes leads to a welcoming entrance, highlighted by a stone pathway and a classic white porch railing.
Home in Andover
4.9 out of 5 average rating, 20 reviews

Andover 3 Bedrooms 2 Baths, Free Parking, Location

Welcome to the historic Shawsheen village in Andover! This 3-bedroom townhouse is right off the I-495 exit and offers easy access. A Dunkin Donut and the highly-rated Shawsheen Luncheonette are both within a 3-minutes' walk. 3-5 minutes' drive to Whole Foods, Stop and Shop, Market Basket, and the train station. 7 Minutes to Phillips Academy. Ideal for remote/group work with multiple work spaces. Commuting to downtown Boston is extremely easy, just hop on the train and leave the car behind!

Top guest favorite
A cozy living area features a dark sectional sofa and a light wood coffee table positioned on a textured area rug. A television is mounted on the wall across from the seating, complemented by a small lamp on a side table. Natural light filters through multiple small windows.
Apartment in Wayland
4.95 out of 5 average rating, 38 reviews

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Top guest favorite
Apartment in Medford
4.93 out of 5 average rating, 367 reviews

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

Superhost
A welcoming living area features a large sectional sofa adorned with decorative pillows and a warm throw. A round coffee table sits centrally, while a wooden dining table for four is positioned nearby. Natural light enters through multiple windows, highlighting the wooden flooring.
Home in Melrose
4.78 out of 5 average rating, 54 reviews

Quiet Entire house, Boston close, MBTA, com rail

QuietSingle family house in premier North of Boston neighborhood. Wonderful for people not great with stairs. Master bedroom, bathroom, Washer/Drier/Dishwasher, kitchen, living room all on same 1st floor. 2 Big TV, BBQ, fire pit, WiFi, backyard patio, radiant floor heating, basketball hoop, scenic walking trails around nearby tri-ponds (w/ fishing), central location to Rte.1, 93 and 95. Walk to the commuter rail, MBTA orange line or 137 Bus route. Have it all, enjoy the city in suburban quiet.

Superhost
A serene waterfront view reveals a calm lake reflecting clear blue skies. A grassy area leads to a sandy beach, with an American flag gently waving nearby. The scene is framed by trees and manicured foliage, providing a peaceful outdoor retreat.
Home in Worcester
4.75 out of 5 average rating, 159 reviews

Private waterfront home!

“La Casita” is a private waterfront home near Umass medical! Modern 1-2 bedroom home with a Master Bedroom on the 2nd floor and a multi use room that can be used as a 2nd bedroom with a full size futon. There is a 3 season porch with a dining nook which leads out to a big outdoor deck. There are multiple ceiling fans and water toys for renters use. No pets or smokers. This is a quiet, family oriented neighborhood with another home on the lot with small children so calm renters only please.

Guest favorite
A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.
Home in Canton
4.87 out of 5 average rating, 39 reviews

Hidden Gem near Boston w/ Private lake access

Waterfront 3BR home 1 mile from commuter rail to Boston. 1 mile from Blue hills ski. 2.2 miles from New England's 1st and only TopGolf. This 3BR, 2.5 BA features an open floor plan w/ view of your private lake from the kitchen and dining rooms. Head downstairs to play pool, ping pong or darts. Or relax by the fire and watch tv (all streaming channels). Warmer months turns into a resort: Fishing, boating, swimming, grill, fire pit, furnished cabanas, hiking the blue hills and much much more.

Superhost
A calm lake scene is depicted, featuring still waters reflecting autumn foliage and a nearby shoreline. A boat is secured at a dock, surrounded by trees, while a clear blue sky enhances the serene atmosphere.
Home in Shrewsbury
4.83 out of 5 average rating, 36 reviews

Lake House near Boston 1

Enjoy the amazing lifestyle on Lake Quinsigamond, while being close to the city center of Worcester. Even if you come to work in the area, it feels like being on vacation. Lots of fun things to do all year around and only 40min to Boston. This 4BR house on 0.3 acres has a large front and back yard. It has a car port for 2 cars, and two docks. Great for short-term rentals. Very close to UMass hospital, grocery stores, gym, restaurants, route 20 and I-90. Pet friendly. Kayaks are available.

Superhost
A serene view of Lost Lake shows a private dock extending into calm waters, with a small motorboat tied at its end. Lush green trees line the shore, providing a natural backdrop to the peaceful setting.
Cottage in Groton
4.92 out of 5 average rating, 52 reviews

Cozy, 2BR lake-side retreat and outdoor oasis

Our cozy, family friendly and completely remodeled lake house enjoys modern conveniences with private lake access and quick access to Boston (only 45 mins!). The vacation getaway is located on Lost Lake in beautiful Groton, MA bordering serene conservation land on 2 sides and facing a small private beach with dock. The location offers a balance of natural beauty with a convenience to amenities allowing you to get away from the fast paced city life but return at your leisure!

Top guest favorite
A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.
Guest suite in Concord
4.98 out of 5 average rating, 142 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Guest favorite
The exterior of a modern home features natural wood shingles and multiple large windows. A well-maintained lawn with diverse greenery surrounds the structure, with colorful plants visible near the base. A wooden deck with stairs leads to a screened-in porch, enhancing outdoor accessibility.
Home in Groton
4.89 out of 5 average rating, 28 reviews

Peaceful home in the woods

Relax with the whole family at this peaceful home in Groton. Private setting off the main road with 10 acres abutting Groton conservation land. A quarter mile walk in the woods right off the property takes you to the beautiful Wattles Pond. Enjoy the open layout with plenty of natural sunlight, cozy living areas, designated office to work from home, and screened in porch overlooking the forest. Your perfect escape that will surely provide lots of relaxation.

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