Pet-friendly vacation rentals in Westerly

Seaside Serenity

Extraordinarily serene & equally stylish, this waterfront cottage on Great Island is the refuge you’ve been longing for! 2 bedrooms & 1 beautifully tiled bath, along with an open cook’s kitchen & living area feature windows everywhere to take in views you will never tire of! Relax on the covered porch or stroll barefoot across the grass to the deep-water dock & adjacent beach area. Located just minutes to Galilee, restaurants, the Block Island Ferry, white sandy beaches, surfing & so much more!

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.

Fireside Delights & Snowy Nights - Sleeps 7

WINTER GETAWAY ALERT: Cozy up on the RI Coast! Welcome to Woodhaus Westerly — a peaceful winter retreat minutes from downtown shops, breweries, and coastal walks. Enjoy 3 private wooded acres for starry-night bonfires, winter trails, and cozy nights by the wood stove with blankets, games, and movies. Dog + kid friendly with plenty of space to relax. Perfect for couples, families, or a remote-work refresh. ☀️Beach Pass returns for Summer 2026! View more photos and updates @Woodhaus_Properties

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Ellis -Lakeside Cabin on Beach Pond with Sauna

Year Roun 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!

Ocean Shire Coastal Retreat + Beach Pass

Relax at this warm modern private coastal cottage. Located 3 miles of Misquamicut and Watch Hill beaches. Season beach pass included. Kids Welcome! 1100 sq. ft, two bedroom, 1.5 bath attached cottage on 1.4 acres. Taylor Swift's Watch Hill home: 3 miles Ocean House Watch Hill: 3 miles Mystic, CT: 10 miles Newport, RI: 38 miles Wooded yard is a beautiful tranquil outdoor space. Easy access to shops, restaurants, bars, sailing, water sports and beach are all available at your door.

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.

Perfect New England Getaway has a pool/ hot tub

traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Cute and Close to Beaches and Town

A cute comfortable 2 bedroom 2 bath home with summer beach parking pass. Recently updated and furnished. A fenced in backyard. Allowing pets. Close to all in Westerly and South County. Grey Sail brewery, shops, restaurants. A 5 minute walk to restaurants, About a mile to Downtown Westerly and Wilcox park. 4 Miles to Misquamicut beach and Watch Hill. Central AC. Fenced in back yard allowing pets Great place to rent year round!

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.