Family-friendly vacation rentals in Watch Hill, Westerly

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Watch Hill, Westerly family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A living area features three comfortable chairs with floral upholstery, arranged around a wooden coffee table. Natural light fills the space through multiple windows. A cozy area rug covers the floor, and a decorative gold side table adds an elegant touch.
Condo in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars2 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
Top guest favorite
A cozy bedroom features a bed dressed in a floral comforter with a decorative pillow. A soft glow from a floor lamp illuminates the space, complemented by a window that offers natural light. A mini-fridge is present in the corner, adding convenience.
Guest suite in Mansfield
4.96 out of 5 average rating, 207 reviews

Cozy private apt 8 mins from UCONN - solar powered

ShinjiRating, 5 stars2 weeks ago
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!
Top guest favorite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork
4.97 out of 5 average rating, 205 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious deck surrounds a large pool, complemented by red umbrellas and lounge chairs. Lush greenery and blooming hydrangeas create a serene backdrop. A cozy seating area is visible under a shaded structure, enhancing the outdoor relaxation space.
Home in East Hampton
4.95 out of 5 average rating, 75 reviews

Family Friendly Springs Beach House

NicholasRating, 5 stars2 weeks ago
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!
Guest favorite
An expansive outdoor area features a heated pool and hot tub, surrounded by lush greenery and tall trees. Lounge chairs with umbrellas are positioned nearby, set against a backdrop of vibrant grass and shaded by mature trees, creating a serene space for relaxation.
Home in Shelter Island
4.88 out of 5 average rating, 25 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

AliciaRating, 5 stars7 months ago
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.
Guest favorite
A welcoming display includes two wine glasses beside a bottle of wine on a granite countertop. A wicker basket holds assorted snacks, while a blue candle and a bouquet of white tulips add a touch of elegance. An information guide is also visible.
Villa in Norwich
4.89 out of 5 average rating, 402 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

JamesRating, 5 stars1 month ago
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
Superhost
The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.
Home in East Hampton
4.76 out of 5 average rating, 135 reviews

Sprawling Hampton Estate w/ Hot Tub +Heated Pool

MarcoRating, 5 stars1 month ago
🌟 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.
Top guest favorite
A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.
Home in North Fork
4.93 out of 5 average rating, 475 reviews

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

BorisRating, 5 stars1 week ago
Wonderful stay. The location was great and the space was perfect for us.

Family- and pet-friendly home rentals

Top guest favorite
A charming white house with blue shutters and a bright blue door is set against a clear sky. Lush green grass surrounds the home, with vibrant pink azaleas and well-maintained hedges adding color to the inviting exterior.
Home in mystic
4.98 out of 5 average rating, 186 reviews

Charming Downtown Mystic Historic House

EllenRating, 5 stars2 weeks ago
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!
Superhost
A well-lit bedroom features a spacious bed with a light blue and white patterned coverlet. A small lamp sits on a bedside table beside the bed. Natural light enters through a large window adorned with blinds, complementing the warm wall color.
Apartment in Newport
4.79 out of 5 average rating, 154 reviews

Downtown Hideaway! Walk to Harbor & restaurants.

KirstenRating, 5 stars2 weeks ago
Great spot. Tons of things to do in walking distance. Cute apartment with everything you could need. Responsive and friendly host.
Guest favorite
A serene view of the home surrounded by lush greenery and blooming trees, reflected in the calm waters of the nearby pond. The property is framed by tall trees, creating a peaceful atmosphere in the rural setting.
Home in Hopkinton
4.88 out of 5 average rating, 122 reviews

Large estate with pond near beaches

SaraRating, 5 stars6 months ago
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.
Top guest favorite
The exterior of a two-story house is shown, featuring light gray siding and black shutters. Window boxes are adorned with flowers. A front porch with steps leads to the main entrance. A fenced yard is visible to the side, complemented by green grass.
Home in Newport
4.97 out of 5 average rating, 288 reviews

Atlantic Street Guesthouse

CinthiRating, 5 stars1 week ago
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
Guest favorite
A tranquil section of the Little River is depicted, featuring cascading water creating gentle ripples. Sunlight reflects off the surface, enhancing its natural beauty. Lush green leaves frame the scene, adding a touch of nature to the flowing water.
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars9 months ago
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!
Guest favorite
The spacious patio is shaded by a vine-covered pergola, featuring a round dining table surrounded by black chairs. Lounge chairs are positioned nearby, and the yard extends beyond, showcasing green grass and a variety of plants, contributing to an inviting outdoor space.
Home in North Fork
4.94 out of 5 average rating, 112 reviews

Maritime Village Getaway with Backyard

LauraRating, 5 stars1 week ago
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!
Guest favorite
The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.
Home in North Fork
4.91 out of 5 average rating, 106 reviews

Cozy Farmhouse Retreat in North Fork, NY

MarisaRating, 5 stars1 month ago
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!
Guest favorite
A spacious living area features a comfortable sectional sofa and a recliner, centered around a coffee table. A well-equipped kitchen area is visible in the background, showcasing light cabinetry and modern appliances. Natural light enters through a nearby window, enhancing the open layout.
Apartment in Middletown
4.88 out of 5 average rating, 305 reviews

3 bedroom near Wesleyan, downtown

JasonRating, 5 stars3 weeks ago
Monica is great! Helpful, clear, prompt communication. Thanks for letting us stay :)

Family-friendly home rentals with a pool

Guest favorite
Home in Montville
4.92 out of 5 average rating, 270 reviews

Casino Wine Down House

MarkavaRating, 5 stars1 month ago
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.
Guest favorite
An in-ground pool is surrounded by a green lawn and tall trees, offering a peaceful setting. Lounge chairs are arranged nearby, and red umbrellas provide shade. A spacious home is visible in the background, enhancing the sense of privacy and relaxation.
Home in East Hampton
4.92 out of 5 average rating, 111 reviews

Private & Pristine with Pool and Kid’s Playard

ChrisRating, 5 stars1 month ago
We had a great stay. Comfortable house with a big yard and pool. Located close to EH village and also the Springs bay beaches.
Top guest favorite
A well-maintained outdoor space features a blue swimming pool surrounded by lounge chairs and a red umbrella. Lush greenery lines the area, and a small shed is visible near the pool's edge, providing a serene atmosphere for relaxation.
Home in North Fork
4.88 out of 5 average rating, 124 reviews

The Perfect North Fork Escape

RenataRating, 5 stars4 weeks ago
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.
Superhost
A spacious backyard features a large swimming pool surrounded by a brick patio. The two-story home, with a screened-in porch and an upper deck, is complemented by lush greenery. A pool house and lounge chairs provide additional relaxation areas.
Home in East Hampton
4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

LisaRating, 5 stars9 months ago
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.
Guest favorite
An above-ground swimming pool is featured in a spacious outdoor area, surrounded by a wooden deck adorned with colorful lounge furniture. Lush greenery provides a tranquil backdrop, enhancing the peaceful rural setting. A paved patio offers additional outdoor space for relaxation.
Guest suite in Brooklyn
4.93 out of 5 average rating, 188 reviews

Affordable In-Law Apartment in Brooklyn, CT

KathyRating, 5 stars3 weeks ago
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.
Superhost
A large, L-shaped pool is surrounded by a spacious concrete deck, featuring a shaded picnic area with a red umbrella, several chairs, and a table. A screened pool house sits in the background, with surrounding greenery and a chain-link fence providing privacy.
Apartment in Brooklyn
4.85 out of 5 average rating, 218 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars7 months ago
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.
Guest favorite
An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.
Home in Sag Harbor
4.86 out of 5 average rating, 265 reviews

Exclusive Sag Harbor Compound

ZacharyRating, 5 stars2 weeks ago
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.
Top guest favorite
A light blue house features a welcoming front porch with bright blue chairs. The well-maintained lawn is surrounded by a white picket fence and shaded by a leafy tree. A gravel driveway leads to the garage, creating an inviting outdoor space.
Cottage in Montauk
4.93 out of 5 average rating, 162 reviews

Montauk Cottage Escape

MarianneRating, 5 stars1 week ago
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

Destinations to explore