
Holiday rentals with a kayak in Westerly
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Westerly
Guests agree: these holiday homes with a 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.❤️

Awesome 3 bed vacation lake house. Great location!
Three bedroom house right on Johnson’s Pond with private water access right in the back yard. House features queen master with deck overlooking the pond. 2nd bedroom features a full bed with twin bunk bed above along with a stand alone twin bed. 3rd bedroom has a queen bed. Perfect for one or two couples to share. Full kitchen and laundry along with WiFi and streaming services. Use of 2 kayaks and pedal boat. Just two miles from I-95, so everything in southern New England is just minutes away!!

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!

Unique Home with Panoramic Ocean and Pond Views
A unique and tranquil getaway, described beautifully by client reviews. Situated on Matunuck Point with sweeping views of the Atlantic Ocean, beautiful Block Island, boats coming in and out of historic Galilee Breach Way or enjoy watching surfers at Deep Hole. Love the beach? We have private access to East Matunuck 100 steps away. If your preference is the pond, Potters Pond is right in the back yard with a new beautiful custom built dock, with paddle boarding, and kayaking equipment.

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!

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly
Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

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.

Beauty and the Beach!
Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

Cozy cottage 5 minutes from UConn
Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

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.

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 Westerly kayak rentals
Holiday House Rentals with a Kayak

Estate with lake near beaches & Westerly

Serenity On The Sound

Lake House w/Game Rm 5 Min From Foxwoods & Mohegan

Classic Lake House~4 Steps to water_FirePit_kayaks

Gorgeous Lake house retreat

Stylish Retreat Waterviews

2 Acre Lakefront Getaway (Sauna/Firepit/Kayaks)

Waterfront House, Sunset Views
Cottages with a kayak

Lake front cottage

3 Bedroom Cottage Gem

Direct Waterfront Cottage on Moodus Reservoir.

Vintage Bolton 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 #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

Mystic Area Waterfront Cabin #5
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 $199 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Westerly holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Easton Beach
- Roger Williams Park Zoo
- Second Beach
- The Breakers
- Mohegan Sun
- South Shore Beach
- Bonnet Shores Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- East Matunuck State Beach
- Fort Adams State Park
- Burlingame State Park
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