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Vacation rentals with a kayak in Worcester County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Worcester County

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

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Guest favorite
A charming two-story house is nestled by the water, featuring a wraparound deck adorned with seating. The landscaped yard includes rocky pathways and a small gathering area with Adirondack chairs, inviting moments of relaxation by the water's edge.
Home in Sturbridge

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

4.94 out of 5 average rating, 330 reviews
Top guest favorite
Cottage in Brimfield

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

4.98 out of 5 average rating, 107 reviews
Guest favorite
A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.
Home in Westminster

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

4.89 out of 5 average rating, 240 reviews
Top guest favorite
The exterior of the house features blue siding with white trim and a welcoming red front door. A small porch is adorned with an American flag. Surrounding greenery and a gravel pathway lead to the entrance, with trees providing a natural backdrop.
Home in Sturbridge

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

Fully equipped w/open lake view living space w/gas fpl. Direct access to Lake w/private dock, (2) kayaks, decks, patio, grill & fire pit. Pvt master bed/bath and 2nd bed w/lake view/deck access. Base rate up to 5 people. $50/each add pers-night max 8 tot. 4th bed is futon in finished walkout bsmt with 3rd full bath. Min 3 night stay. Base weekday $375, Weekend $475. Premium rates seasonally/holidays. Local tax added by AirBnB. Ck-out 11 AM, Ck-in 3 PM unless arranged. Sorry no more pets.

4.96 out of 5 average rating, 186 reviews
Top guest favorite
Home in Ashburnham

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!

5.0 out of 5 average rating, 39 reviews
Top guest favorite
Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

4.96 out of 5 average rating, 157 reviews
Top guest favorite
A modern two-story house with large triangular windows is set against a twilight sky. The elevated structure features a spacious deck wrapped with a railing, providing outdoor seating options. The ground level showcases garages, and soft lighting highlights the exterior architecture.
Home in West Brookfield

Peaceful Lake Escape w/ Porch, Fire Pit & Kayak

Escape to this charming West Brookfield lake retreat! This 3BR, 2BA home sleeps 8 and features 1,700 sq ft of open-concept space, a wraparound porch, and an outdoor fire pit. Enjoy walking access to the lake and cozy evenings under the stars, perfect for families and friends seeking a classic New England getaway. Salem Cross Inn - 3min drive Lake Wickaboag - 5min walk West Brookfield Town Common - 5 min drive Rock House Reservation - 10 min drive Brookfield Orchards - 10 min drive

4.91 out of 5 average rating, 111 reviews
Guest favorite
A wooden deck offers high-top chairs facing a tranquil lake surrounded by trees. The scene includes a spacious grassy area leading to the water, with a gazebo visible in the distance. A gentle mist adds a serene quality to the landscape.
Home in Union

Antique Home w Private Pond, Sturbridge /Brimfield

Minutes to Sturbridge, great craft breweries, (including TreeHouse), Brimfield Antique Flea Market. Our recently ( and ongoing) renovated 1800s farm house is ready for your next stay. It is quirky and not for perfectionists! Visit nearby Old Sturbridge and its many great shops and restaurants, and nearby State Parks. Plenty of room, fully equipped kitchen, comfy living rm & big dining room. 3 comfortable bedrooms upstairs. Very easy off/on the highway to be on your way quickly!

4.83 out of 5 average rating, 162 reviews
Top guest favorite
Home in Sterling

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!

5.0 out of 5 average rating, 39 reviews
Top guest favorite
A private outdoor patio area features a round table surrounded by four chairs, positioned on a brick surface. A swing chair is visible nearby. The peaceful lake view extends beyond, framed by trees and rolling hills under a bright blue sky.
Cottage in Holland

Cozy Lakefront Cottage

Welcome to our rustic, seasonal cottage on the lake. Perfect for couples or friends looking for a quiet getaway, or small families w/kids beyond toddler age. Newly renovated. Clean & comfortable. Use of the entire cottage, including; 2 bedrooms, well equipped kitchen, comfortable living room w/flat screen TV & DVD player, screened in porch, private outdoor patio & small beach area w/dock, & 3 kayaks. Centrally located near Sturbridge w/easy access to I-84 & MassPike.

4.96 out of 5 average rating, 102 reviews
Guest favorite
A cozy house is framed by tall trees, with a snow-covered landscape surrounding it. The exterior features a combination of warm wooden siding and a brick chimney. A large screened porch is visible, offering a seamless connection to nature.
Home in Holland

D. Chief's Lodge Cheerful Cabin at the Camp

Year round house: you'll have a great time at this comfortable place to stay. Camp Mishnoah, a former Girl's Club Camp, is undergoing restoration into a wellness retreat. This rental is a stand alone house. A very comfortable queen size bed and a single bed in a separate bedroom, lodge style living room with a vaulted ceiling, full kitchen, bathroom with shower and a half bath. Access to the pond and hiking trails. Nearby Sturbridge Village and Tree House Brewery.

4.91 out of 5 average rating, 125 reviews
Guest favorite
A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.
Cabin in Winchendon

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

4.96 out of 5 average rating, 137 reviews

Popular amenities for Worcester County kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favorite
A vibrant sunset paints the sky in hues of pink, orange, and purple above a tranquil lake. The water reflects the colorful sky, creating a serene atmosphere. Silhouettes of trees line the horizon, enhancing the peaceful view.
Home in Webster

Webster Waterfront Cottage Nestled in the Pines

4.86 out of 5 average rating, 134 reviews
Guest favorite
A stone fire pit is surrounded by four adirondack chairs, situated on green grass alongside a tranquil lake. Lush trees frame the view, with a subtle reflection of the landscape visible on the water's surface.
Home in Leicester

Scenic Lakehouse w/ Kayaking & Canoeing

4.82 out of 5 average rating, 73 reviews
Guest favorite
The lakeside retreat presents a spacious outdoor area with well-maintained greenery and seating options. A charming deck with comfortable seating overlooks the water, while several tall trees provide shade. Nearby, a small boat dock can be seen, enhancing the lakeside ambiance.
Home in Sturbridge

Lake House in Sturbridge w/All the Views!

4.99 out of 5 average rating, 71 reviews
Superhost
A serene lakeside view is presented, with several docks extending into the water. Leafless trees frame the scene, while a grassy area leads to the water's edge, creating an inviting space for outdoor activities.
Home in Sterling

Charming lakeside cottage.

4.89 out of 5 average rating, 57 reviews
Guest favorite
A serene three-season porch is showcased, featuring large windows that provide views of the lake and surrounding greenery. Comfortable seating is arranged around a wooden coffee table, with a dining table nearby. Bright natural light fills the space, enhancing the tranquil atmosphere.
Home in Sturbridge

Chic & Modern Studio Lakefront House with Loft

4.86 out of 5 average rating, 93 reviews
Superhost
Home in Shrewsbury

Lake House near Boston 1

4.79 out of 5 average rating, 57 reviews
Top guest favorite
Home in Ashburnham

Cozy, year-round Lakefront Retreat.

5.0 out of 5 average rating, 17 reviews
Top guest favorite
Home in Hopkinton

Waterfront Retreat | Dock, Kayak & Lake Views

4.95 out of 5 average rating, 19 reviews

Cottage rentals with a kayak

Top guest favorite
A tranquil scene of a calm lake reflecting lush green trees and charming homes along the shoreline. A wooden dock provides access to the water, while kayaks rest on the bank, inviting exploration of the serene surroundings.
Cottage in Westminster

Cottage @ Partridge Pond

4.98 out of 5 average rating, 97 reviews
Superhost
Cottage in Dudley

Cozy, 3BR lake-side retreat and outdoor oasis

4.85 out of 5 average rating, 54 reviews
Guest favorite
Cottage in Gardner

Otter's Paradise

4.91 out of 5 average rating, 43 reviews
Top guest favorite
A charming light blue house is positioned near the water, surrounded by tall trees. A small deck with steps leads to the water's edge, which features a private dock. The grassy area in front adds to the serene outdoor setting.
Cottage in Orange

Lake House with view of mountain

4.99 out of 5 average rating, 96 reviews
Guest favorite
Cottage in Holland

Hamilton Cottage | Cozy Lakefront A-Frame

4.97 out of 5 average rating, 38 reviews
Top guest favorite
A charming cottage is set amidst colorful autumn foliage, with a gravel driveway leading up to the entrance. Large windows allow natural light to enter, while a wooden deck is visible at the side, showcasing a welcoming outdoor area with surrounding greenery.
Cottage in Wales

Sunset and Sunrise views at this lake cottage.

4.97 out of 5 average rating, 76 reviews
Top guest favorite
A serene lakeside retreat is surrounded by lush green trees and a gently sloping shoreline. The main structure features a covered porch offering views of the tranquil water. Light fluffy clouds frame the bright blue sky, enhancing the peaceful natural setting.
Cottage in Ashburnham

Cottage with private beach and boats to cruise in

4.96 out of 5 average rating, 68 reviews
Top guest favorite
Cottage in Stow

Waters Edge

4.92 out of 5 average rating, 12 reviews

Cabin rentals with a kayak

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

Secluded Rustic Lakeside Cabin - Perfect Escape

4.94 out of 5 average rating, 85 reviews
Guest favorite
A comfortable living area features a dark sofa, a brown leather armchair, and a wooden coffee table. Wall art and photographs add character, while a unique light fixture hangs above. Natural light streams in from the window, illuminating the warm wood flooring.
Cabin in Athol

Panoramic Sunroom | Soaking Tub | Modern Cabin

4.94 out of 5 average rating, 99 reviews
Guest favorite
A serene lake scene is captured at sunset, with golden sun reflections shimmering on the water's surface. Silhouettes of trees line the horizon, and a few ducks can be seen floating peacefully on the lake.
Cabin in Webster

The Camp

4.9 out of 5 average rating, 182 reviews
Top guest favorite
Cabin in Sturbridge

Mermaid Cove | Private Lakefront Escape

4.91 out of 5 average rating, 11 reviews
Guest favorite
A rustic log cabin is set among lush greenery, featuring a patio area with four red chairs arranged around a stone fire pit. Large windows offer views of the surrounding nature, while a wooden deck extends from the cabin, providing additional outdoor seating.
Cabin in Douglas

Rustic Log Cabin on the Lake

4.96 out of 5 average rating, 23 reviews
Top guest favorite
A spacious deck offers comfortable seating with cushions in shades of blue and gray. A modern coffee table sits in the center, surrounded by trees, providing an unobstructed view of the calm water and distant shoreline.
Cabin in Webster

Private Island on Webster Lake

5.0 out of 5 average rating, 16 reviews
Top guest favorite
Cabin in Sturbridge

Hideaway Cabin on Cedar Lake | Dock, Loft & Deck

5.0 out of 5 average rating, 16 reviews
Top guest favorite
A calm lake is viewed at sunset, with vibrant hues of orange and yellow reflecting on the water's surface. Soft blue and gray clouds contrast the warm colors, while trees line the shore in silhouette against the fading light.
Cabin in Tyngsborough

Modern Rustic Elegance on a Lake - Perfect Escape

5.0 out of 5 average rating, 42 reviews

Destinations to explore