Holiday rentals with a pool in Westerly

Find and book unique homes with a pool on Airbnb

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Popular amenities for Westerly rentals with a pool

House rentals with a pool

Top guest favourite
Home in Montauk
5 out of 5 average rating, 77 reviews

3 BR/Pool. Walk to Beach & Town!

KevinRating, 5 stars3 days ago
Great hidden little gem in MTK, close to town. Perfect space inside, and out. Pet friendly was an extreme plus. Will be back.
Guest favourite
Home in Middletown
4.96 out of 5 average rating, 69 reviews

Secluded Oasis w/ Heated Pool - 10 mins to Newport

LyndseyRating, 5 stars3 days ago
Beautiful, well decorated and SO clean. The location is ideal- only a few minutes to all the attractions in Newport. The heated pool was amazing since the weather was only in the 70s when we visited. The host was very responsive and helpful. I would definitely stay here again.
Top guest favourite
Home in East Lyme
5 out of 5 average rating, 28 reviews

Niantic Getaway w/ Pool, Spa & Many Activities

RoseRating, 5 stars6 days ago
We loved the home and yard. Beautiful is the best description with so many seating options. The house is bright and inviting. The hosts have done a great job decorating and providing so many amenities not even listed. I would recommend this beautiful home to anyone wanting a place to relax and enjoy what is there.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars1 month ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.
Top guest favourite
Home in East Hampton
4.93 out of 5 average rating, 43 reviews

Sunny, walk to beach, large pool

KrithiRating, 5 stars2 weeks ago
We had a lovely weekend at Rachel's cozy abode! The home was perfect for a few of us working remotely for the week. We were able to enjoy the peaceful backyard & pool and the house was stocked with all the kitchen essentials we needed to cook a few meals at home. The location of the house is also great--we enjoyed the quick drives to nearby beaches and our dinner outings. Rachel was communicative, kind, and responsive. We hope to be back for another getaway in the near future!
Guest favourite
Home in North Fork
4.92 out of 5 average rating, 88 reviews

Modern farmhouse w/ pool, beach, horses and winery

XiuRating, 5 stars1 week ago
I had a wonderful stay! The place was exactly as described—clean, cozy, and well-equipped. The host was friendly and responsive, making check-in and check-out super easy. The neighborhood was quiet and convenient, perfect for relaxing after a day out. I would definitely stay here again and highly recommend it to anyone visiting the area!
Guest favourite
Home in Sag Harbor
4.86 out of 5 average rating, 269 reviews

Exclusive Sag Harbor Compound

Amy RoseRating, 5 stars2 weeks ago
Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.
Top guest favourite
Home in North Stonington
4.93 out of 5 average rating, 15 reviews

Stylish Retreat near Mystic, Foxwoods, vineyards…

CaroleannRating, 5 stars10 months ago
Scott’s house was absolutely gorgeous, and exactly as advertised. We walked in to a beautiful gift basket with local wine and the makings for s’mores, which was such a thoughtful touch. There was a handbook that explained where everything in the house was located and made some local recommendations like restaurants and things to do. The house was well-stocked and the outdoor area was thoughtfully furnished and spacious. It was very close to Foxwoods, a local winery, and Mystic Pizza II. We loved staying in Scott’s beautiful home, and highly recommend it!

Apartment rentals with a pool

Superhost
Apartment in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars1 month ago
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again
Top guest favourite
Apartment in Norwich
4.97 out of 5 average rating, 38 reviews

Modern Loft Villa, 1 mile to Mohegan Sun

KaraRating, 5 stars6 days ago
we have taped at other Villas. this one was wonderful. part of the reason I picked this one was due to sleeping arrangements. a bonus that I didn't get at other villas was a code to the back gate, which made an easy drive to Mohegan even easier. it was nicely decorated and Erin was very responsive when I had a few general questions
Guest favourite
Apartment in Montauk
4.89 out of 5 average rating, 28 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

MarielRating, 5 stars5 months ago
Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!
Guest favourite
Apartment in Norwich
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars1 month ago
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen
Superhost
Apartment in Old Saybrook Center
4.89 out of 5 average rating, 74 reviews

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.
Top guest favourite
Apartment in Norwich
5 out of 5 average rating, 32 reviews

Mohegan Sun Escape-Hot Tub/Pool/Golf & Norwich Spa

MikealaRating, 5 stars3 weeks ago
Nat was incredibly friendly, welcoming, and easy to communicate with! Her cute and clean little condo was the perfect spot for my husband and I to get away for his 40th birthday weekend! Conveniently located near the casinos and our favorite- spas! Thank you Nat!
Guest favourite
Apartment in Newport
4.92 out of 5 average rating, 36 reviews

1BR Condo w/ Bay Views + Jacuzzi Tub

SylviaRating, 5 stars2 months ago
We had the best time. It's on the list to do again.
Top guest favourite
Apartment in Montauk
4.95 out of 5 average rating, 120 reviews

Deluxe Studio Apt@The Montauk Manor

ChristinRating, 5 stars8 months ago
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Home rentals with a private pool

Guest favourite
Bungalow in East Hampton
4.93 out of 5 average rating, 108 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars8 months ago
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.
Top guest favourite
Home in East Hampton
4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

LaelRating, 5 stars1 month ago
Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!
Guest favourite
Home in East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars8 months ago
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
Guest favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars9 months ago
One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!
Home in East Hampton
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars35 months ago
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.

Quick stats about holiday rentals with a pool in Westerly

  • Total rentals

    10 properties

  • Nightly prices starting at

    $219 SGD before taxes and fees

  • Total number of reviews

    590 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

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