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.

1 of 1 pages1 / 1

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

4.74 out of 5 average rating, 163 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 second 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. Heating/AC provided by mini splits & 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.

ValueLocationBathroom

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

4.88 out of 5 average rating, 51 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.

Outdoor spacesValueGetting around

Top guest favorite

Apartment in Medford

4.93 out of 5 average rating, 393 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.

ValueLocationAmenities

Guest favorite

A charming lake house is depicted by the water, showcasing a light blue exterior and a welcoming front porch. The reflection in the calm lake adds depth to the scene, surrounded by lush greenery and hints of fall colors in the trees.

Home in Westminster

4.84 out of 5 average rating, 193 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!

Outdoor spacesLocationParking

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, 45 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.

Outdoor spacesLocationIndoor spaces

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

4.8 out of 5 average rating, 50 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.

LocationOutdoor spacesPets

Top guest favorite

Home in Ashburnham

5 out of 5 average rating, 39 reviews

The Nutty Bird Lakehouse

Charming lakefront featuring 2 cozy bedrooms comfortably accommodating up to 4 guests, w/2 bathrooms. Nestled in nature, this home offers breathtaking lake views—perfect for relaxing with a good book and a hot cup of coffee. Enjoy the propane firepit on lower deck. For those looking for adventure, each season brings unique activities: swim, hike, and fish in the summer, or enjoy ice skating, sledding, snowshoeing, & scenic drives in winter. Embrace the beauty and tranquility year-round!

LocationSleep qualityView

Guest favorite

Apartment in Concord

4.96 out of 5 average rating, 24 reviews

Concord Riverfront Place

Beautiful, spacious, one bedroom apartment in historic Concord home. Located on the Sudbury River with private entry, full kitchen, gas fireplace, separate study area. Walk out to a lovely patio area overlooking the Sudbury River. Canoe and kayak directly from the property. Short walk to shops, restaurants and historic sites of Old North Bridge, Alcott , Emerson houses, Walden Pond and more . Short walk to the commuter rail to Boston. Easy access to Route 2. Close to 128/495.

LocationOutdoor spacesAmenities

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

4.91 out of 5 average rating, 55 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!

LocationOutdoor spacesFamily

Top guest favorite

Home in Sterling

5 out of 5 average rating, 30 reviews

Stunning Sterling Sanctuary: Unwind on the Water!

Feel your worries drift away along the freshwater when you stay at this spacious 3-bedroom, 1.5-bath Sterling vacation rental! Nestled on the serene shores of East Waushacum Pond, this home ensures a fun-filled stay for all. Spend your days exploring the water-by kayak or paddle board-and put your toes in the sand at Sterling Town Beach! When the sun sets, cook a delicious dinner on the gas grill and roast s'mores over the fire for dessert. Adventure is calling -book now!

LocationOutdoor spacesNearby

Top 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

4.95 out of 5 average rating, 80 reviews

Secluded Rustic Lakeside Cabin - Perfect Escape

Take it easy at this peaceful and secluded lakefront getaway. Escape to our log cabin nestled in the woods on the shores of a pristine lake in Groton, Massachusetts, less than an hour from Boston. The cabin blends rustic charm with modern comfort and offers a quiet setting to relax and unwind. Enjoy lake views, fresh air, and the sounds of nature. This home is best suited for quiet family vacations and responsible adult travelers seeking a peaceful lake retreat.

Outdoor spacesLocationHiking

Guest favorite

Guest suite in Canton

4.72 out of 5 average rating, 134 reviews

Newly renovated, close to Foxboro and Boston

Only 10 miles to Foxboro stadium!Private guest suite surrounded by nature and a large yard featuring a large POOL (closed Sep-May) with beach entry and pool slide. Next to Blue Hills and pond, a nature escape close to Boston! Nature trail right by your door! An additional unit with queen bed is available as well. Queen size bed, bathroom, WIFI, smart TV, kitchenette with microwave, coffee maker, toaster, fridge. Stove in a shared kitchen. Massage chair.

Outdoor spacesValueGrill