Vacation rentals with a pool in Westerly

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Popular amenities for Westerly rentals with a pool

House rentals with a pool

Top guest favorite
Home in The Hamptons
5 out of 5 average rating, 75 reviews

3 BR/Pool. Walk to Beach & Town!

AndyRating, 5 stars5 days ago
From the beginning of my booking Adam provided a real friendliness to ensure we had a great visit. Went the extra mile to help with getting situated with a 2 year old...and I would recommend this place to ANYone. It was perfect beach vibe with an amazing pool, great bikes/chairs/etc for enjoyment...and it's a 5 min walk to town (for the true Montauk experience). Loved it and thank you Adam!!!
Top guest favorite
Home in East Lyme
5 out of 5 average rating, 27 reviews

Niantic Getaway w/ Pool, Spa & Many Activities

WilliamRating, 5 stars2 weeks ago
We (short-term owners of three years) had a fantastic week-long stay with a group of 7! The house was impeccably clean and well-stocked with everything we needed. Check-in was a breeze, and the hosts were incredibly attentive, kind, and quick with helpful suggestions. The variety of games and activities—especially the record player, fire pits, hot tub, and air hockey—kept us entertained. All amenities were ready for use, making our stay truly enjoyable. Highly recommend! Jennifer and Erich, well done. Thank you
Guest favorite
Home in Groton
4.91 out of 5 average rating, 33 reviews

A Mystic Dreamscape: Pool, Winery, Mystic Aquarium

SandyRating, 5 stars8 months ago
Shelone was spacious and comfortable. Ideal for big families or a group trip. My family and I felt cozy in her home on our weekend getaway in CT. We were celebrating my birthday and my family surprised me with a birthday brunch. Shelones kitchen had everything equipped to make a full family meal. The rooms were comfortable and accurately described in the pictures. Living room area perfect for comfy gathering with family. The location of the house is in a quiet neighborhood but a short 8 min drive away from Mystic and 20 min drive to Mohegan soon. I traveled with small children, and let Shelone know. The house was equipped with all amenities needed for a family with young children, play pen, stool, hair chair, games. Thank you Shelone for hosting us ! We definitely enjoyed our time in your home.
Guest favorite
Home in North Fork
4.94 out of 5 average rating, 34 reviews

Bailey House

ZarinaRating, 5 stars8 months ago
It was a lovely stay. Great location. House felt like a home and had great vibes.
Superhost
Home in The Hamptons
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars2 weeks 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.
Guest favorite
Home in Tiverton
4.92 out of 5 average rating, 25 reviews

Waterfront Oasis Pool EPIC Views

MicheleRating, 5 stars1 week ago
Our family just had a wonderful time at Stacy and Mario‘s house. The house was immaculate, comfortable and extremely well appointed. The views were beautiful especially the sunsets. The hosts were extremely responsive and considerate
Guest favorite
Home in The Hamptons
4.86 out of 5 average rating, 266 reviews

Exclusive Sag Harbor Compound

RobertRating, 5 stars2 weeks ago
Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!
Guest favorite
Home in The Hamptons
5 out of 5 average rating, 21 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

MeganRating, 5 stars1 month ago
Beautiful home, really well stocked and super comfortable. Warm, clean and lots of amenities. Comfortable beds, good showers, big lovely kitchen. Lots of space. We had a great stay. Thanks :)

Condo rentals with a pool

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

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars3 weeks 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
Guest favorite
Condo in The Hamptons
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!
Superhost
Condo in North Fork
4.84 out of 5 average rating, 135 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

SeanRating, 5 stars2 weeks ago
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.
Guest favorite
Condo in Uncasville
4.97 out of 5 average rating, 30 reviews

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

CarlyRating, 5 stars1 month ago
Natalie was a great host, super communicative which was very much appreciated. The place was beautiful and a perfect stay for 2 couples!
Guest favorite
Condo in Uncasville
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars2 weeks 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
Top guest favorite
Condo in Norwich
5 out of 5 average rating, 32 reviews

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

MikealaRating, 5 stars2 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 favorite
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.
Guest favorite
Condo in Newport
4.91 out of 5 average rating, 35 reviews

1BR Condo w/ Bay Views + Jacuzzi Tub

JenniferRating, 5 stars1 month ago
Clean, comfortable, friendly atmosphere. Jenny and Ania were super helpful from booking until checkout. I would definitely stay with them again. Thank you for making the vacation with my son so wonderful.

Home rentals with a private pool

Guest favorite
Home in The Hamptons
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 favorite
Bungalow in The Hamptons
4.93 out of 5 average rating, 107 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 favorite
Home in The Hamptons
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!
Home in The Hamptons
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 vacation rentals with a pool in Westerly

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$35,566 GYD 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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