Vacation rentals with a kayak in Worcester County

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Top-rated kayak rentals in Worcester County

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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

4.9 out of 5 average rating, 193 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

Top guest favorite

Cabin in Thompson

4.99 out of 5 average rating, 135 reviews

Secluded cabin w/ Finnish Sauna & Forest Baths

A secluded, romantic, rustic, cabin alongside the French River - Frog Hollow is a perfect place to get away and experience the luxury of a wood fired sauna and forest baths. Located in the Quiet Corner of CT, relax as you watch the ducks, herons, turtles, and beavers along the river. Cook a delicious meal in the porch-enclosed kitchen, cozy up next to the woodstove fireplace, work remotely with a water view, or go for a paddle on the river. Ideal for a couple or solo traveler wanting to unwind.

Guest favorite

The exterior of a renovated cabin features a light yellow façade and a gray metal roof. A small wooden deck with a railing provides access to the entrance, which showcases a black door with a glass panel. Surrounding trees add to the natural setting.

Tiny home in Holland

4.96 out of 5 average rating, 107 reviews

C. Chief Cook delightful tiny house

Enjoy peaceful surroundings of this rustic destination. Come relax at this former camp under renovation. Hang out by Lake Siog where you can paddle board, kayak, use the rowboat, find a meditation site, light a campfire or just rock on the hammock. Lake Siog has a number of hiking and biking trails and the Quinebog River Canoe Trail. We are close to the Brimfield Antique Flea Market, Palmer Antique Co-ops, Old Sturbridge Village and restaurants, wineries, and breweries like Treehouse Brewery.

Guest favorite

Cabin in Winchendon

4.95 out of 5 average rating, 58 reviews

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 (our apologize but it is currently not working) 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.

Top guest favorite

The exterior of a historic farmhouse is showcased among lush green grass and mature trees. The property features multiple buildings, including a red barn, and the main house displays a welcoming red door. A spacious lawn invites relaxation and outdoor activities.

Farm stay in Ashby

5 out of 5 average rating, 20 reviews

The Wellington House

Enjoy the exquisite natural beauty surrounding this beautiful historic getaway. Beautifully restored and maintained 1860 Farmhouse updated and fully appointed for your comfort. Property boasts fabulous views of 3 acre pond with private waterfall. Every window has views looking out over rolling fields and at horses grazing in adjacent pastures. Beautiful gardens, walking trails and a quintessential farm house porch for relaxing or work. The farm abuts hundreds of acres of State Wildlife land.

Guest favorite

A spacious wooden table with benches is positioned beneath a screened-in porch, surrounded by lush greenery. Natural light filters through the screens, highlighting the inviting view of the water beyond, creating an ideal space for meals or relaxation.

Cottage in Holland

4.98 out of 5 average rating, 49 reviews

Blissfully Peaceful Cottage nestled on a lake

Relaxing and quaint cottage nestled on the pristine and bountiful waters of the Hamilton Reservoir. Perfect place to step back with the family and take a much needed timeout to reconnect with your loved one(s). The reservoir is pristine and is clear up to 4’ down. Perfect for swimming or just relaxing on the private beech located steps away. Be our guest, come out and enjoy this peaceful place and take the time to make memories that will last a lifetime. Looking forward to hosting you!

Guest favorite

A two-story lakeside home is depicted, surrounded by trees and greenery. A private dock extends into the water, accompanied by kayaks and a spacious deck. Natural stone steps lead from the dock to the house, providing access to the patio and outdoor living space.

Home in Sturbridge

4.96 out of 5 average rating, 171 reviews

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.

Top 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

4.98 out of 5 average rating, 83 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

Located on a large serene pond, The Retreat at Eagleville is perfect for fishing enthusiasts, nature lovers, family fun, and anyone looking for an escape from the hustle of the city. Enjoy glamping amenities including a soaking tub, fully-equipped kitchen, outdoor BBQ & griddle, and a covered pavilion with picnic table. Relax by the firepit, unwind in the hammock, or lounge in Adirondack chairs. ☞ Complimentary wood for 1st fire ☞ No checkout rules ☞ Linens provided ☞ Self Check-in

Superhost

An outdoor seating area is surrounded by lush greenery, featuring arranged stone pathways and a fire pit. The dock extends into the water, accommodating boats, while the nearby lake house displays a charming screened porch among the trees.

Home in Sturbridge

4.87 out of 5 average rating, 61 reviews

Chic & Modern Studio Lakefront House with Loft

Indulge in a remarkable escape at our elegant and enchanting lake house! Tucked away on the stunning Cedar Lake, your personal 3 season porch, patio, and dock await as our inviting haven combines serene relaxation with thrilling adventures. Discover the meticulously appointed main living space, accompanied by a generously equipped full-sized kitchen and bathroom. With ample space for 2 adults and 2 children, our abode is the ultimate family sanctuary or a secluded romantic haven.

Top guest favorite

A welcoming living area features a vibrant red sofa and a matching chair arranged around a small white side table. Natural light fills the room through two windows, illuminating a decorative rug on polished wooden floors. A bookshelf is positioned nearby, housing various games and books.

Apartment in Leicester

4.98 out of 5 average rating, 82 reviews

Sunny 2-Bdrm Apartment at the Barred Owl Retreat

This 2-bedroom apartment at the Barred Owl is on the second floor of historic home on the Worcester/Leicester line near all Central MA attractions. Wander the trails by streams and ponds; visit with chickens; hike; kayak. We will share fresh eggs, vegetables, and flowers from the gardens. Meditate, rest in the hammock. Can be rented as 2 bedroom or 4 bedroom. (see other listing) Kitchen is small but has all you need; there is AC for warm summer days.

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

4.94 out of 5 average rating, 33 reviews

Charming lakeside cottage.

Charming lakeside cottage is the perfect place to enjoy coffee in the am or a paddle at sunset. This home has 1.5 baths, and 2 bedrooms. The smaller bedroom has a queen bed. The larger bedroom has 2 sets of trundle beds to sleep 4 people. The kitchen is fully stocked with all you need to entertain just bring food. We have some toys for kids if needed. We have a few kayaks and a pedal boat you can use at your own risk or bring your own.

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

4.98 out of 5 average rating, 64 reviews

Cottage @ Partridge Pond

Relax on Partridge Pond. Great for paddle boarding and swimming or just hanging out on the deck/dock and grilling. Great local restaurants and Wachusetts brewery 5 min up the road and Wachusetts ski area 10 min away. Local hiking trails and golf course nearby. Newly furnished. Updated utilities. Quiet area and a great retreat. Year round entertainment. We enjoy our time here. This is a ‘pet-free’ property.