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Vacation 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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Condo in Norwich

4.88 out of 5 average rating, 211 reviews

The N-V ...The Spa at the Norwich Inn.

Welcome to The Spa @ the Norwich Inn Villas.. Updated with lightness and comfort in mind. You open to an updated kitchen with all the amenities you’ll need for your stay ..and of course your Keurig stocked up for u. You’ll be walking on engineered flooring with suppressed corking for comfort and sound reduction. The dining is a well designed top with stools that tuck away..just in case you need the Queen sized Murphy bed.. Master bedroom has a queen bed, private bathroom, 32” tv and full WiFi.

Aug 16 – 23

G$31,071 GYD per night

Apartment in Norwich

4.9 out of 5 average rating, 228 reviews

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

THE POOL IS OPEN AS OF MAY 1st! Welcome to our charming 2-bedroom apartment. This centrally located spot is the perfect getaway to escape the hustle and bustle of the big city and enjoy a more relaxed pace of life. The unit comes in at a spacious 950 sq ft - ideally suited for couples, solo travelers, families and can comfortably accommodate up to 4 people. Feel free to use the grill of course, but you may have to fill the propane tank. You can do so at the Walmart which is 12 minutes away!

Sep 24 – Oct 1

G$21,283 GYD per night

Condo in Norwich

4.99 out of 5 average rating, 167 reviews

Modern & Cozy Villa with low cleaning charge!

Located on the Norwich Inn and Spa property, this Villa is a true one bedroom unit with access to two clubhouses (9am-10pm) which include a sauna, gym, hot tub, and saltwater pool access (seasonal). It is also located a few miles away from both Mohegan Sun Casino and Foxwoods Resort and Casino with many amazing restaurants to chose from in the area. If you are a fan of golf, we are located right on the back 9 of the Norwich Golf course! Lake of Isles golf course is also about 15 minutes away.

Oct 16 – 23

G$44,174 GYD per night

Apartment in Stonington

4.89 out of 5 average rating, 164 reviews

The Schoolhouse, Stonington, CT

Enjoy the many activities that this small fishing village has to offer: restaurants, farmers markets, a beach that overlooks Long Island Sound, and tennis/paddle board, churches, kayaking. All within a 5-10 minute walk. You never have to drive your car! The apartment has a private back entry into a spacious first floor kitchen, bath, bedroom, two large living rooms; the front living area has floor to ceiling windows facing the front porch which is available for sitting on a hot summer night.

Mar 18 – 25

G$42,997 GYD per night

Apartment in Bristol

4.96 out of 5 average rating, 135 reviews

Cozy, Peaceful One Bedroom Apartment in Bristol

Cozy peaceful one bedroom apartment centrally located in picturesque Bristol. Located on a dead end street. Just a 20 minute walk to downtown, Colt State Park and waterfront. Centrally located between Providence and Newport and Boston and the Cape. Enjoy amenities such as; pool, private deck, espresso and tea bar, and Netflix . Enjoy all Bristol has to offer: museums, Saturday market, fantastic restaurants, boating, beach, quaint shops and of course the oldest continuous 4th of July Parade!

Feb 26 – Mar 5

G$24,580 GYD per night

Condo in Montauk

4.99 out of 5 average rating, 181 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Nov 16 – 23

G$62,973 GYD per night

Condo in Norwich

4.99 out of 5 average rating, 112 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.

Oct 26 – Nov 2

G$32,265 GYD per night

Home in Stonington

4.97 out of 5 average rating, 185 reviews

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.

Jan 14 – 21

G$108,048 GYD per night

Guest suite in North Kingstown

4.83 out of 5 average rating, 610 reviews

Morgan Cottage

We Know it's Winter and it's cold outside but you will love our cozy, relaxing, self contained one bedroom apartment, with its private access. Get away for a day or two or more for an invigorating forest or beach walk or explore the scenic south county or hang out in one of the funky bars and restaurants that are found from East Greenwich to Newport. And we are just a 10 minute stroll to the historic village of Wickford with its quaint shops and 18th Century seaside charm.

Sep 19 – 26

G$34,571 GYD per night

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Feb 1 – 8

G$15,413 GYD per night

Guest suite in Newport

4.88 out of 5 average rating, 400 reviews

★2 BEDROOM SUITE★ Wyndham Newport Onshore Resort!

Bundled between the majestic waters of Newport Bay and Historic Thames St. shopping, dining, and drinking, the Newport Onshore Resort will be the ideal New England stay. With Newport as the "Yatching Capital of the World," it is the perfect place to experience all types of boating activities, so once you charter your boat for the day, you can come back and unwind in one of the many pools or sweat it out in the fitness center located on site.

Nov 26 – Dec 3

G$31,960 GYD per night

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

Beautiful, deluxe studio apartment with every amenity. Registered historical landmark. Magnificent lobby with fireplace, restaurant. Cable TV with HBO, DVD and WI FI. The in-door pool, jacuzzi and sauna are not available due to renovations) The restaurant is open at various dates and times off season. Call the Montauk Manor for more information. Don’t miss out on the fabulous beaches.

Mar 12 – 19

G$36,227 GYD per night

Vacation rentals for every style

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Popular amenities for Westerly rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Oct 8 – 15

G$191,805 GYD per night

Home in New London

4.89 out of 5 average rating, 132 reviews

OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS

Feb 14 – 21

G$203,748 GYD per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Nov 11 – 18

G$47,390 GYD per night

Home in Exeter

4.89 out of 5 average rating, 109 reviews

Nature's Nook

Sep 25 – Oct 2

G$61,877 GYD per night

Home in Montville

4.96 out of 5 average rating, 106 reviews

Casino Stay & Play House

Jun 3 – 10

G$108,519 GYD per night

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Oct 23 – 30

G$144,486 GYD per night

Home in Westerly

4.95 out of 5 average rating, 19 reviews

Minutes to the beach, pool, + beach pass! Westerly

Feb 28 – Mar 7

G$96,957 GYD per night

Home in Westerly

5.0 out of 5 average rating, 11 reviews

Misquamicut Beach House, 1 Mile From the Ocean!

Oct 1 – 8

G$108,091 GYD per night

Condo rentals with a pool

Condo in Norwich

4.9 out of 5 average rating, 146 reviews

Renovated Condo rental at Norwich inn villa & Spa

Aug 18 – 25

G$38,879 GYD per night

Condo in Montauk

4.8 out of 5 average rating, 232 reviews

Montauk Royal Atlantic Beach Resort North

Oct 17 – 24

G$42,966 GYD per night

Condo in Greenport

4.83 out of 5 average rating, 145 reviews

Sound front condominium

Apr 29 – May 6

G$151,015 GYD per night

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Oct 20 – 27

G$63,289 GYD per night

Condo in Greenport

4.92 out of 5 average rating, 125 reviews

Beautiful Waterview Condo on the North Fork of LI

Sep 22 – 29

G$90,998 GYD per night

Condo in Montauk

4.82 out of 5 average rating, 158 reviews

Coastline View Studio

Oct 29 – Nov 5

G$238,880 GYD per night

Condo in Norwich

5.0 out of 5 average rating, 39 reviews

Villla, king bed, Spa, casinos, hot tub, pool

Nov 17 – 24

G$27,802 GYD per night

Condo in Norwich

4.98 out of 5 average rating, 57 reviews

Spa-KING bed-Casino-HotTub-Pools-Massage chair

Oct 31 – Nov 7

G$45,492 GYD per night

Home rentals with a private pool

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Oct 10 – 17

G$201,814 GYD per night

Home in East Hampton

4.79 out of 5 average rating, 39 reviews

Enchanting Home with Large Decks and Heated Pool

Mar 25 – Apr 1

G$120,405 GYD per night

Bungalow in East Hampton

4.93 out of 5 average rating, 99 reviews

East Hampton Ranch with Access to Clearwater Private Beach

May 29 – Jun 5

G$127,753 GYD per night

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Apr 1 – 8

G$155,999 GYD per night

Quick stats about vacation rentals with a pool in Westerly

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
720 reviews
Nightly prices starting at
G$25,101 GYD before taxes and fees

Destinations to explore