
Family-friendly vacation rentals in Watch Hill, Westerly
Find and book unique family-friendly homes on Airbnb
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
Get the amount of space that is right for you
Popular amenities for Watch Hill, Westerly family-friendly rentals
Family-friendly home rentals with a hot tub

Villa Flora @ Norwich Inn & Spa
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

Cozy private apt 8 mins from UCONN - solar powered
The place was quiet, surrounded by beautiful woods, and truly relaxing—it was exactly what I needed. The bed was incredibly comfortable, and I slept so well each night. I also appreciated how responsive the host was to my questions via text. I would love to stay there again in the future. Thank you so much!

Private Oasis W/Stunning Vinyard and Pool Views
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

Family Friendly Springs Beach House
Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

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.

Peaceful Spa Escape minutes to Mohegan Sun Casino
Stay was great, enjoyed the Spa and the hot tub ! I wish the hot tub closing times were posted somewhere but other than that it was great ! Fire place was a also very cool and the fire starter that is supplied was very helpful

Sprawling Hampton Estate w/ Hot Tub +Heated Pool
🌟 A Perfect Hamptons Getaway – Highly Recommend! 🌟 We had the pleasure of staying at this beautiful Airbnb in the Hamptons for two days, and it was everything we hoped for and more. The home is a stunning blend of modern elegance and cozy charm. The interiors are tastefully decorated, creating a warm and inviting atmosphere. We especially loved the spacious living areas and the well-equipped kitchen, which made meal preparations a joy. Our host was exceptional responsive, accommodating, and genuinely kind. This Airbnb exceeded our expectations in every way.

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
Wonderful stay. The location was great and the space was perfect for us.
Family- and pet-friendly home rentals

Charming Downtown Mystic Historic House
We had a wonderful stay! The location couldn’t be better and the home was so comfortable and welcoming. All the information was clear and James was very responsive. We would definitely stay again!

Downtown Hideaway! Walk to Harbor & restaurants.
Great spot. Tons of things to do in walking distance. Cute apartment with everything you could need. Responsive and friendly host.

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.

Atlantic Street Guesthouse
We had a wonderful stay with our kids and dogs. The property is in a great location - close to restaurants, shops, etc. Scott is super helpful and welcoming. The kids appreciated all the snacks! One of our favorite Airbnb stays - highly recommend and would stay again!! Thanks for everything Scott

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!

Maritime Village Getaway with Backyard
I stayed at Mary's rental with my sister's family including a 4yo and 6yo, as well as my 72yo mother and the house was a perfect fit! The downstairs bedroom and full bath were perfect for mom to avoid the steep stairs, and the house was well equipped with a ton of kids books and some toys. Proximity to town was the highlight, we were easily able to walk with the kids which was perfect since the weekend was too chilly for the beach. Mary was responsive if needed but the house is well stocked and easy to navigate so we felt at home right away. I will absolutely be renting from Mary again!

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!

3 bedroom near Wesleyan, downtown
Monica is great! Helpful, clear, prompt communication. Thanks for letting us stay :)
Family-friendly home rentals with a pool

Casino Wine Down House
Friendly and prompt responder. Really clean. The kids more than loved the game room. And I personally loved the decor. Only objection is it’s kinda out of the way and you’d have to drive to do any activities, but other than that a really great stay.

Private & Pristine with Pool and Kid’s Playard
We had a great stay. Comfortable house with a big yard and pool. Located close to EH village and also the Springs bay beaches.

The Perfect North Fork Escape
Laurie’s home was the perfect size for our girls weekend to celebrate the bride. The patio was extensive and comfortably fit all of us for a hibachi chef and dinner. It was a quick drive from the house to the wineries, which was fantastic.

Gorgeous East Hampton Getaway
Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Affordable In-Law Apartment in Brooklyn, CT
We had an excellent stay while attending our son's graduation at UCONN. The place was clean and homey, perfect when traveling back and forth. Our plans changed and we did not bring our dog, and Ashley was kind enough to refund us. My son goes back to UConn in the fall for his master's, and we know where we will stay again next May.

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.

Exclusive Sag Harbor Compound
Beautiful house in the Hamptons! Loved visiting Sag Harbor and spending time at Benjamin’s house. Benjamin was accommodating and provided everything for an enjoyable trip. Looking forward to returning in the future.

Montauk Cottage Escape
A beautifully kept home just right for a few people. The two bedrooms were physically far apart which is an advantage if you want to have noise-privacy, but distant if you have young children and want to be nearer to them. Well appointed kitchen and hosts were easy to communicate with. Lovely yard and hosts were easy to communicate with. Very well done accommodation!
Quick stats about vacation rentals that are family-friendly in Watch Hill, Westerly
Total rentals
10 properties
Nightly prices starting at
$320 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
- Charlestown Beach
- Southampton Beach
- Brown University
- Foxwoods Resort Casino
- Easton Beach
- Napeague Beach
- Cooper's Beach, Southampton
- Shinnecock Hills Golf Club
- TPC River Highlands
- Roger Williams Park Zoo
- Amagansett Beach
- Quotonset Beach
- Ocean Beach Park
- Giants Neck Beach
- Blue Shutters Beach
- Point Judith Country Club
- Oakland Beach
- South Shore Beach
- South Jamesport Beach
- Attawan Beach
- Groton Long Point South Beach
- Fort Adams State Park
- Clinton Town Beach
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