Holiday rentals with a pool in Westerly

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Westerly

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Home in Stonington

4.87 out of 5 average rating, 113 reviews

Homestead Near Mystic, Casinos & Beaches

Welcome to our peaceful home set on a semi-secluded 3 acre wooded lot near Mystic! Our home features a tasteful nautical theme that honors coastal New England. You will love to relax by the pool in summer or cozy up to the basement bar in winter after a fun day exploring the region. Come to de-stress from life in a tranquil setting or to explore the area. We are centrally located to the hip food and waterfront scene in Mystic, both major casinos, Block Island ferry, and all the historical sites.

Guest favourite

Home in New London

4.9 out of 5 average rating, 173 reviews

Sunset Oasis 2 @ Ocean Beach: Ranch w/ 6 Queen

Last of Aug Summer '25 Days Open : Mon 8/18 - Thurs 8/21 or Mon 8/25 - Thurs 8/28 INSTANT BOOK: Aug '25 - Jan New Year '26 All Open Availability Peaceful Waterfront Views of Alewife Cove Upper Back Porch (year round) & Lower Outdoor Patio Furniture (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Guest favourite

Villa in Norwich

4.89 out of 5 average rating, 405 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

Superhost

Home in East Hampton

4.87 out of 5 average rating, 210 reviews

HeatedPool, Walk2Beach, FencedYard4Pup, Spotless

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Superhost

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Top Guest favourite

Condo in Norwich

4.98 out of 5 average rating, 195 reviews

Peaceful Oasis steps from Mohegan Sun

Feel at home at our contemporary yet cozy villa. A private and quiet space in the heart of the area's local attractions (walkable to Mohegan Sun/short drive to Foxwoods). Perfect for a fun-filled weekend or a simple and quiet getaway. Enjoy the scenic views of the surrounding golf course or indulge at the on-site renowned spa. Other noteworthy amenities include a year round opened clubhouse, sauna, and hot tub as well as two beautiful seasonally opened pools. This unit comfortably sleeps 4.

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 157 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Guest favourite

Home in Stonington

4.99 out of 5 average rating, 111 reviews

4BR Private Indoor Heated Pool - Lux Mystic Home

Experience Mystic in style at this spacious retreat featuring a private heated indoor pool (additional fee applies). Relax poolside, cook in the gourmet kitchen, or explore the charming town center. Designed for comfort and convenience, this home is perfect for groups with four king beds, an open-concept living area, and a cozy outdoor patio for evening relaxation. Whether you're seeking adventure or relaxation, this coastal getaway is your perfect escape! Min. Age 25. Govt ID required.

Top Guest favourite

Home in Scituate

4.97 out of 5 average rating, 159 reviews

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. Pool has surcharge $20 if weather is good during your stay.

Top Guest favourite

Home in North Fork

4.98 out of 5 average rating, 166 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Top Guest favourite

Condo in Norwich

4.94 out of 5 average rating, 177 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Guest favourite

Home in New London

4.9 out of 5 average rating, 137 reviews

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!