
Family-friendly vacation rentals in Watch Hill, Westerly
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Top-rated family-friendly rentals in Watch Hill, Westerly
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Watch Hill, Westerly family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Flora @ Norwich Inn & Spa
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

Cozy private apt 8 mins from UCONN - solar powered
This is a wonderful place to stay if you are visiting UConn or the surrounding area. Keri and Jason were fabulous hosts and very responsive to my needs. Keri even anticipated needs by offering to have a fresh cup of coffee ready for me on the AM. Everything was perfect for my stay and there was definitely a comfortable feel. I will definitely be staying here in the future.

Private Oasis W/Stunning Vinyard and Pool Views
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

Perfect New England Getaway has a pool/ hot tub
Absolutely beautiful home with every amenity and comfort. You can tell how much love and care went into this place- every piece of furniture and detail is the highest quality. It’s even more spacious and beautiful than it looks in the photos. It was perfect for our group with young kids and it was great they provided a pack and play so we didn’t have to pack one. The hosts were easy to communicate with and flexible. They even let us check out late on our final day. We opted to enjoy the beautiful yard and home longer rather than venture out because we were so comfortable. We cannot wait to come back in the summer as the pool and yard set up is incredible. Thank you for a wonderful stay!

Newly Renovated w/ Pool, Hot tub & Fireplace
We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.

Captains Quarters | July avail!
This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Sprawling Hampton Estate w/ Hot Tub +Heated Pool
Perfect place to stay in East Hampton! The house is large and can comfortably sleep 15. Backyard is great and Warren was quick to respond whenever we wanted to heat the pool. Location is ideal, very close to East Hampton and Amagansett towns. Very clean as well! I would definitely stay here again and would recommend it to anyone

Lakeside cottage with beautiful views up the lake!
We had a relaxing, peaceful time at Bobby's place. It's wonderful to wake up right on the water. He was very communicative. It is quiet, but still close enough to everything. We had an enjoyable experience.
Family- and pet-friendly home rentals

Boutique Hotel Special pricing available
This was our first trip with our 10 month old baby and it was everything we could have hoped for. The location is amazing, walkable to everything. The hosts were so responsive. Literally would respond within 2 minutes of texting. They had a pack n play and high chair ready for us in the apartment when we got there. They also let us check in a bit early so that our baby could take her afternoon nap on time. They gave great recommendations on places to eat and things to do. 10/10 would recommend to anyone!

Large estate with pond near beaches
This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.

Rustic Retreat,unique home, minutes to Newport, RI
The rustic retreat was a cozy vintage inspired house that felt very homey. It was 5 minutes from great coffee shops and downtown Newport. It was great to be able to bring our dog. My daughter loved the secret bamboo garden ‘room’. Would definitely stay again. Lillian was very hospitable! Thank you!

Entire Home Close to Beach and Downtown!
The place was great. Very charming house with plenty of room. Very easy to find as well. Roland was great. Super responsive and flexible!! If I make it to Middletown again I’ll stay here again for sure!

House on Little River / Writer Retreat
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

⚓️ Top Notch Newport Location! SuperHost! 🏡
Lovely trip to Newport. Location of this house is perfect. Everything was clean and nice and super super easy communication. We forgot some small items and the hosts went above and beyond to mail them back to us.Great stay.

Cozy Farmhouse Retreat in North Fork, NY
This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!

Casa Bungo | Walk to Surf Lodge, Beach & Town!
We had a wonderful stay at Steffen & Sara's charming bungalow! The location was incredibly convenient, check in was a breeze, and the house was comfortable, well-appointed, and inviting. The house was meticulously clean and well-maintained. Steffen & Sara were incredibly responsive and accommodating, making sure we had everything we needed for a great stay. We would absolutely stay here again and highly recommend it to anyone looking for a great place to stay in the area!
Family-friendly home rentals with a pool

Casino Wine Down House
House was very easy to get to and very clean. Surrounding neighborhood was nice and quiet. Outside igloo was warm and cozy. Downstairs game room was a hit with the big kids.

Private & Pristine with Pool and Kid’s Playard
Marta’s place was the perfect getaway for my family. The bedrooms were large with comfortable beds. The kitchen was huge with high end appliances, and the yard was a dream for our young dog. Lovely surroundings in the woods but close to town for shopping and restaurants. Truly an unforgettable experience!

The Perfect North Fork Escape
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Modern East Hampton Home w/ Heated Saltwater Pool
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Affordable In-Law Apartment in Brooklyn, CT
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!

8 Bedroom, 4 full bath residence with 40' pool
This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.

Montauk Oceanview Studio 6
I love the easy access to the beach! It felt like a private beach in comparison to the downtown Montauk, which is exactly what I needed! Location is definitely great!

Exclusive Sag Harbor Compound
We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!
Quick stats about vacation rentals that are family-friendly in Watch Hill, Westerly
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ1,175 before taxes and fees
Total number of reviews
170 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Ocean House, Watch Hill Lighthouse, and Olympia Tea Room
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- Beach
- Brown University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Clinton Town Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Roger Williams Park Zoo
- Oakland Beach
- Shennecossett Beach
- Long Island Aquarium
- Groton Long Point Main Beach
- Attawan Beach
- South Shore Beach
- Barbara Pine Memorial Beach
- Grove Beach
- Horton Lane Beach
- Avery Point Beach
- Groton Long Point South Beach