
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.

Crow's Nest Stonington Borough
Two floor private suite in antique quaint and cozy mansard. in your space is hot pot/teas, microwave, toaster, washer and dryer - shared refrigerator, ice. Fresh Coffee provided each am in a thermos. Airy upstairs bedroom with half bath, queen bed, full cable tv and water view. Downstairs private dining room/sitting area with queen sleep sofa, full bath. Stonington Borough is the quintessential charming seaside village - stroll and explore all breakfast/dinner options five minute walk 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!

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.

Kayaks and Glimpses of Westport Bay
Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

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.

Waterfront Cottage with Dock
Arts & Crafts cottage with dock on ocean cove and close to the beaches. You’ll love the backyard and waterfront fire pit. Canoe, kayak and paddle boards are complimentary. Bring your own boat or rent one for 50% off at Stonington Marina. On same cove as Saltwater Farm Vineyard, and nearby to Mystic Aquarium, Mystic Seaport, Foxwoods and Mohegan Sun resorts. My place is good for families with kids and pets. Cottage HVAC has been upgraded to an eco friendly central AC and heat pump.

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
The Lake House boasts an outdoor patio with a dog-run, complimentary kayaks for exploration, and a cozy fire pit under the starlight sky! ● 333 Mbps Wi-Fi | 43” Smart UHD TV | Washer & Dryer ● Nintendo (NES) w/ 30 Games | Board Games | Puzzles ● 4x Kayaks | Watercraft Trolleys | Horseshoe Pit ● Patio w/ Fire Pit & Gas Grill| Full Kitchen | Coffee (Keurig) Drive to: UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

The Perch
Spring is in the air, encouraging lots of walks around the lake, visits to the local wineries and lovely 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.

2 Acre Lakefront Getaway (Sauna/Firepit/Kayaks)
Step into our beloved lakeside haven on Pasquiset Pond, a place where comfort meets tranquility. Whether you're in search of a peaceful retreat or a cozy spot to reconnect with family, our home offers a warm and inviting escape, perfect for any season. When you're ready to explore, you'll discover beautiful beaches just 10-15 minutes away, along with the unique charm and vibrant local culture that make this area special.
Popular amenities for kayak rentals in Westerly
House rentals with a kayak

Estate with lake near beaches & Westerly

Coastal New England Waterfront Home-The Reed House

The Surf Shack - Ocean Views From Every Room

Cozy cottage 5 minutes from UConn

Unique Home with Panoramic Ocean and Pond Views

Luxe Bolton Lake

Gorgeous Lake house retreat

Luxury Cottage on the Potowomut River 2bd/2b
Cottage rentals with a kayak

Lake front cottage

Riverview beach cottage

Little Boho Retreat by the Beach

Direct Waterfront Cottage on Moodus Reservoir.

Go Jump in the Lake!

Beautiful lakefront retreat just 15 mins to casino

Waterfront, Dog-Friendly Cottage on the Cove

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

Casa Lago

The Colchester Cottage

Maxwell Mays Lakefront Cottage

Secluded Lake House

Riverfront Antique Cabin in the Heart of Madison

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Vinola-Lakeside Cabin on Beach Pond with Sauna
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 $180 SGD per night before taxes and fees

Verified guest reviews
Over 970 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!
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Portland Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- House rentals Westerly
- Rentals with beach access Westerly
- Apartment rentals Westerly
- Pet-friendly rentals Westerly
- Rentals with a fireplace Westerly
- Flat rentals Westerly
- Rentals with a hot tub Westerly
- Family-friendly rentals Westerly
- Rentals with a firepit Westerly
- Rentals with outdoor seating Westerly
- Rentals with a washing machine and dryer Westerly
- Fitness-friendly rentals Westerly
- Rentals with pools Westerly
- Waterfront rentals Westerly
- Cottage rentals Westerly
- Rentals with breakfast Westerly
- Beach house rentals Westerly
- Rentals with a patio Westerly
- Beachfront rentals Westerly
- Rentals with a kayak Washington County
- Rentals with a kayak Rhode Island
- Rentals with a kayak United States
- Brown University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Charlestown Beach
- Ocean Beach Park
- Bonnet Shores Beach
- Southampton Beach
- Easton Beach
- Mystic Aquarium
- Mystic Seaport Museum
- Roger Williams Park Zoo
- Second Beach
- The Breakers
- Narragansett Town Beach
- Point Judith Lighthouse
- Hammonasset Beach State Park
- University of Connecticut
- Powder Ridge Mountain Park & Resort
- University of Rhode Island
- Easton's Beach
- South Shore Beach
- Wölffer Estate Vineyard





