Vacation rentals with a kayak in Westerly

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Top-rated kayak rentals in Westerly

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Top guest favorite

A serene lake scene captures a modern gray house surrounded by vibrant autumn foliage. The water reflects the house and trees, creating a harmonious composition. A wooden deck is visible, leading toward the tranquil lake, enhancing the peaceful atmosphere of the setting.

Home in North Stonington

4.96 out of 5 average rating, 126 reviews

The Perch

Great weather is on its way and our lake is the perfect place to celebrate, swim and kayak! Nestled in the trees on a quiet lake this home is designed to be a sanctuary and a launch pad for outdoor adventures. Visit the town of North Stonington, Stonington, Westerly and Mystic then return to your quiet spot. It features sweeping views and an open living space. A short drive to store, casinos, wineries, forest for hikes and 95. (We have added a generator to our list of amenities, just in case!)

Guest favorite

A serene view of the home surrounded by lush greenery and blooming trees, reflected in the calm waters of the nearby pond. The property is framed by tall trees, creating a peaceful atmosphere in the rural setting.

Home in Hopkinton

4.88 out of 5 average rating, 128 reviews

Large estate with pond near beaches

Let this be your home away from home. Large, open, & upscale, with a cozy mix of comfort & nostalgia. Enjoy time with family & friends in our spacious, welcoming home on 40 acres, surrounded by fields, orchards, woods, stone walls, & lake with canoe, kayaks & paddle boards. Great for family vacations, reunions, retreats, & celebrations. Weddings welcome - contact owner for details. Pet friendly. Close to beaches, Watch Hill, Foxwoods. 5 min to I-95. 35 min to Providence airport. 4 night min

Top guest favorite

A private deck is furnished with two comfortable chairs and a small table, offering a view of the serene cove and surrounding greenery. The space is set against a backdrop of trees and open water, creating a peaceful outdoor retreat.

Guesthouse in North Kingstown

4.99 out of 5 average rating, 278 reviews

The Boathouse61

Recently built studio above "The Boathouse". Feel pampered in this airy studio space w/ kitchenette, bath, king bed, & sitting area. Relax on private 2nd story deck overlooking the cove. Kayak to Historic Wickford, paddle around Rabbit Island, the various marinas, or out Narragansett Bay! Enjoy spectacular views, a breathtaking sunrise & fabulous restaurants. 15 mins to TF Green Airport, <30 mins to Providence, Newport, & Narragansett, 20 mins to URI, & less than a mile to Wickford Village.

Top guest favorite

Two Adirondack chairs are positioned near the water's edge, facing a tranquil pond. Sunlight reflects off the water surface, with a small table placed between the chairs. Lush greenery and a tree provide a serene backdrop.

Home in South Kingstown

4.99 out of 5 average rating, 149 reviews

Waterfront Secluded Home with Dock

Nestled down a private road, enjoy a lovely waterfront home with sweeping 180 degree views of Potter’s Pond. Newly renovated and meticulously decorated. Unwind and relax on the back deck watching the extensive variety of birds and breathtaking sunsets. Spend your days exploring the pond in kayaks or try your hand at clamming, steps from the house. Located 1 mile from East Matunuck Beach, 1 mile from Tennis, Pickleball and Basketball courts. Walking distance to the renowned Matunuck Oyster Bar.

Guest favorite

Cabin in Voluntown

4.94 out of 5 average rating, 684 reviews

Ellis -Lakeside Cabin on Beach Pond with Sauna

"Ellis" is a fully heated/winterized camp cottage built in the 1960's by the students of Ellis Tech. It has two bedrooms and sleeps 5. The detached bunkhouse has 3 single beds and is available for larger groups (summer only) Very peaceful lakeside location just 238 feet from Beach Pond. Walking distance to trails. Enjoy the quintessential lakeside vacation! This is not a secluded space so make sure to look at the photos to see the layout of other nearby buildings. Please read all the details!

Top guest favorite

A spacious front porch features contemporary outdoor seating with scenic views of the ocean. The deck is surrounded by a low railing and includes a table, inviting relaxation while enjoying the coastal surroundings. Lush greenery and a pathway are visible beyond the porch.

Home in Narragansett

4.98 out of 5 average rating, 125 reviews

The Surf Shack - Ocean Views From Every Room

This home was featured in the June 2021 issue of SO RI magazine! Located on a quiet cul-de-sac this home has a welcoming front porch with ocean views, an open concept family room w/ fireplace, a spacious eat-in kitchen and a park-like backyard. Private beach connects to Scarborough State Beach. There are 3 king bedrooms and a separate kids room. Master bath has a jacuzzi tub and 2nd bath has a standing rain shower with sprawling marble sink. House has towels, beach chairs and bikes.

Top guest favorite

An outdoor dining area is situated in the yard, featuring a large table surrounded by white chairs, shaded by a yellow canopy. A grill is positioned nearby on a sandy patio, with greenery and a two-story house visible in the background.

Home in Stonington

4.99 out of 5 average rating, 106 reviews

New Stonington Waterfront

Beautiful new five bedroom, four bath waterfront home on Wequetequock Cove in Stonington, built in 2021. Water views from the house and backyard patio, with outdoor dining area and fire pit. Sandy Point, Napatree Beach, East Beach Watch Hill and Dubois Beach are all accessible by car or boat. Paddle to Saltwater Farm Vineyard up the Cove, or explore Barn Island Nature Preserve. Just minutes from Stonington Borough, Downtown Mystic, Mystic Seaport, Mystic Aquarium, Westerly and Watch Hill.

Top guest favorite

The view showcases a serene lake setting, with shoreline trees providing natural framing. A wooden deck extends outward, leading down to the water. Kayaks and a paddle boat are visible on the lake, inviting potential activities for guests.

Home in Preston

5 out of 5 average rating, 190 reviews

New Lake Front Home w/ Game Room & Stunning Views

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

Top guest favorite

A bright living area showcases a comfortable leather sofa paired with a colorful accent chair. Large windows allow natural light to fill the space, while a small globe and decorative items add a touch of character. Wooden floors complement the cozy atmosphere.

Cottage in Groton

4.96 out of 5 average rating, 328 reviews

Charming Historic Schoolhouse on Mystic River

Enjoy stunning Mystic River views from this newly renovated 1BR/1Bath historic schoolhouse. Originally built in 1857 as a one-room school and later relocated, this charming retreat blends historic charm with modern comfort. Thoughtfully furnished to honor its past, it offers a cozy, inviting space for families or couples, to relax and explore Mystic’s rich history, scenic beauty, and waterfront attractions. Perfect for a memorable getaway in a storied New England setting.

Guest favorite

The living area features a large sectional sofa with a throw pillow, a dark coffee table, and a dining area with a wood table. Sliding glass doors open to a scenic view of the Thames River and the outdoor deck.

Home in Montville

4.91 out of 5 average rating, 144 reviews

Thames River Cottage · Near Casinos + USCGA

4 MILES from MOHEGAN SUN! FREE EV LVL-2 Charging! Come relax at the cottage on the Thames River w/ direct river view and access, free Kayaks on site for use, spacious patio, firepit, gas grill, privet boat launch/dock. 10 min from CT College & USCGA, 20-25 min drive to Foxwoods, Mystic, Stonington, Vineyards, local breweries, New London Navy Base, Pfizer, GD (EB) & Mitchell. Cottage is located at the end of Point Breeze (Horton Cove side) with direct river access.

Top guest favorite

A light-filled living area features a cozy couch and an armchair, with a wooden coffee table displaying magazines and a remote. A television with a streaming box is present, and indoor plants add a touch of greenery. Large windows provide views of the deck outside.

Guesthouse in South Kingstown

4.95 out of 5 average rating, 230 reviews

Cute Little House in Town

Cute little guesthouse perfect for two people, but could also work for three with advance notice. There is a queen bed upstairs, and a couch downstairs, there are two fold out cots available upon request. The deck overlooks the huge backyard. The television has a Roku boxes so you can watch Netflix, Amazon Videos, etc. I have a friendly dog named Barney who is often outside on the property.

Top guest favorite

A charming cabin with a red exterior sits surrounded by colorful autumn foliage, reflecting on the calm surface of a pond. A spacious deck is visible, featuring a patio chair and table, while a kayak rests nearby on the grassy shore.

Cabin in North Stonington

4.97 out of 5 average rating, 224 reviews

Summer’s in full swing. Get to the cabin!

Come to the woods of Southeastern Connecticut and enjoy some solitude and connection in the woods while wrapped in our flannel LL Bean bathrobes. Snuggle with a glass of wine or coffee by the fire and unplug, rest, and rejuvenate with your partner or by yourself. Only fifteen minutes away from casinos, shopping or restaurants in Mystic or downtown Westerly, RI.