
Holiday rentals with a kayak in Westerly
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Westerly
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Mystic, CT Pet-Friendly Cottage with Hiking Trails
Unwind at this peaceful, private Cottage with a fenced garden courtyard. Enjoy onsite hiking trails, EV chargers, an outdoor lounge, hammocks, firepit, lawn games, and a gas grill. Your stay includes organic breakfasts and eco-friendly amenities. Just 6 miles from Mystic, the Cottage is your dream escape. Book your stay now and create lasting memories with your pet! ❤️The Cottage books fast for weekends, holidays, & all of summer and fall. We recommend booking soon to guarantee your getaway.❤️

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

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.

Ellis -Lakeside Cabin on Beach Pond with Sauna
Year round quintessential lakeside vacation! Ellis is a fully heated/winterized camp cottage just steps from beautiful Beach Pond. 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. Visit our 6 horses. 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!

Stunning Waterfront Cottage with Big Yard & Dock!
Escape to the tranquil beauty of "A Summer Place," a charming 1,500 sq ft waterfront cottage nestled just steps from RI's stunning coastline and pristine beaches. Whether you're planning a family getaway or a retreat with friends, this idyllic home offers the perfect blend of rural charm and modern amenities, all in a prime location near local shops, bakeries, cafes, and top-rated restaurants. The expansive yard and private dock provide an unbeatable setting while you sit back and relax!

Waterfront cottage overhanging the water!
Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

Beautiful Home on Connecticut Shore
Spacious home in the peaceful neighborhood of Eastern Point. Natural beauty surrounds the home with stunning water views from the front porch and a public beach and golf course just blocks away. Located midway between Boston and New York with Mystic just ten minutes away, this classic New England getaway is perfect for families and friends gathering from around the East Coast, international travelers, vacationers with pets, and visitors to local colleges.

The Perch
Fall is in the air, encouraging lots of walks around the lake, visits to the local wineries and brisk walks on the beaches of Rhode Island. Nestled in the trees on a quiet lake this home is designed to be a sanctuary and a launch pad for outdoor adventures. Visit North Stonington, Stonington, Westerly and Mystic then return to your quiet spot. A short drive to store, casinos, wineries, and a walk to the forest for hikes.

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.

Historic Waterfront School House
Escape to a historic 1857 schoolhouse cottage on the Mystic River. This unique 1-bed, 1-bath waterfront retreat is perfect for couples or solo travelers. Enjoy stunning views of the Mystic Drawbridge and Seaport from your private patio. Just a 2-block walk to historic Downtown Mystic, this charming space combines authentic history with modern comfort for an unforgettable stay.

Waterfront Bliss Tiny Home
Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Come to the woods and snuggle in front of the fire
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.
Popular amenities for kayak rentals in Westerly
House rentals with a kayak

Serenity On The Sound

Narrow River Save! nite/week/month GetaWay! kayaks

Classic Lake House~4 Steps to water_FirePit_kayaks

Gorgeous Lake house retreat

Stylish Retreat Waterviews

2 Acre Lakefront Getaway (Sauna/Firepit/Kayaks)

Water Views | Kayaks & Bikes | EV Charger | Pets

Waterfront House on Fort Pond, MTK
Cottage rentals with a kayak

3 Bedroom Cottage Gem

Direct Waterfront Cottage on Moodus Reservoir.

Vintage Bolton Lake

Go Jump in the Lake!

Beautiful lakefront retreat just 15 mins to casino

Lakefront peaceful getaway cottage

Waterfront, Dog-Friendly Cottage on the Cove

Cottage 29 - Waterfront Cottage - Close to Newport
Cabin rentals with a kayak

Mystic Area Waterfront Cabin #3

Mystic Area Waterfront Cabin #1

Casa Lago

Lakeside Landing

Vinola-Lakeside Cabin on Beach Pond with Sauna

Mystic Area Waterfront Cabin # 2

Lakefront - King - W&D - Fire Pit - Kayaks - Stand Up Paddleboards

Lakeshore Cabin with boat dock
Quick stats about holiday rentals with a kayak in Westerly

Total holiday rentals
Explore 20 holiday rentals in Westerly

Nightly prices starting at
Westerly holiday rentals start at $178 SGD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Westerly holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Westerly rentals

4.9 Average rating
Westerly stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a kayak Washington County
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- Rentals with a kayak United States
- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Easton Beach
- Roger Williams Park Zoo
- Second Beach
- Mohegan Sun
- The Breakers
- East Matunuck State Beach
- Bonnet Shores Beach
- Hammonasset Beach State Park
- South Shore Beach
- Mystic Seaport Museum
- Powder Ridge Mountain Park & Resort
- Burlingame State Park
- Fort Adams State Park
- Salty Brine State Beach
- Orient Beach State Park
- East Hampton Main Beach
- Narragansett Town Beach
- Meschutt Beach




