Family-friendly vacation rentals in Watch Hill, Westerly

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

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, 150 reviews

Villa Flora @ Norwich Inn & Spa

DebraRating, 5 stars6 months ago
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.
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, 205 reviews

Cozy private apt 8 mins from UCONN - solar powered

TerryRating, 5 stars1 month ago
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.
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, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars4 months ago
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!
Top guest favorite
Home in Stonington
4.97 out of 5 average rating, 219 reviews

Perfect New England Getaway has a pool/ hot tub

DanaRating, 5 stars3 weeks ago
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!
Guest favorite
A renovated bathroom features a white bathtub with an attached shower, a modern toilet, and a double sink vanity. Above the sink, a large mirror is framed by bright lighting. White paneling is present on the lower walls, enhancing the clean aesthetic.
Home in Shelter Island
4.88 out of 5 average rating, 24 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

AliciaRating, 5 stars6 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 modern bathroom is featured with white tiled walls and a textured floor. A glass shower enclosure is positioned alongside a wall-mounted sink. A mirror reflects soft light from an overhead pendant, while a small plant adds a touch of greenery to the serene space.
Home in East Hampton
5 out of 5 average rating, 16 reviews

Captains Quarters | July avail!

PeterRating, 5 stars1 month ago
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.
Superhost
A spacious living area features a mix of comfortable seating, including a green sofa and brown lounge chairs. A large flat-screen TV is mounted on the wall, and natural light enters through multiple windows, highlighting the modern decor and warm tones throughout.
Home in East Hampton
4.76 out of 5 average rating, 134 reviews

Sprawling Hampton Estate w/ Hot Tub +Heated Pool

SarahRating, 5 stars8 months ago
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
Guest favorite
A spacious living room features a combination of comfortable sofas arranged around a coffee table. Natural light shines through large windows, illuminating the wood-beamed ceiling. Decorative string lights add a warm glow, while a side table holds a lamp. A playful atmosphere is invited for relaxation.
Cottage in Ledyard
4.93 out of 5 average rating, 247 reviews

Lakeside cottage with beautiful views up the lake!

JimRating, 5 stars2 weeks ago
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

Guest favorite
A bright living area features a comfortable gray sofa and armchair, complemented by wooden flooring. Natural light fills the space through large windows adorned with light blinds. A granite countertop kitchen area is visible, offering modern appliances and a small dining space with a wooden table.
Condo in Newport
4.92 out of 5 average rating, 650 reviews

Boutique Hotel Special pricing available

NikkiRating, 5 stars1 week ago
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!
Guest favorite
Home in Hopkinton
4.88 out of 5 average rating, 122 reviews

Large estate with pond near beaches

SaraRating, 5 stars4 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.
Guest favorite
A cozy living area features a rustic wood stove, a comfortable armchair with a decorative cushion, and a dark brown sofa. Natural light enters through the window adorned with bamboo shades, illuminating the wooden floor. A unique shelving unit displays various items, adding character to the space.
Home in Middletown
4.96 out of 5 average rating, 274 reviews

Rustic Retreat,unique home, minutes to Newport, RI

MaryRating, 5 stars6 months ago
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!
Superhost
The bathroom features soft blue tiles on the walls, paired with a light-colored vanity and a circular mirror. Natural light filters through a window, illuminating the space with sheer curtains hanging alongside. A towel and toiletries are neatly organized, contributing to a tidy appearance.
Home in Middletown
4.9 out of 5 average rating, 134 reviews

Entire Home Close to Beach and Downtown!

JoshRating, 5 stars1 month ago
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!
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 stars7 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
Home in Newport
4.91 out of 5 average rating, 161 reviews

⚓️ Top Notch Newport Location! SuperHost! 🏡

DemitriRating, 5 stars5 months ago
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.
Guest favorite
A cozy seating area features a light gray armchair with tropical leaf print cushions. A stylish black console table holds decorative items and magazines, with a woven basket beneath. Natural light illuminates the space, highlighting the nearby staircase and wall art.
Home in North Fork
4.91 out of 5 average rating, 104 reviews

Cozy Farmhouse Retreat in North Fork, NY

MarisaRating, 5 stars2 weeks 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
An open living area features a colorful sofa adorned with a striped blanket, paired with a round coffee table. Large windows invite natural light, illuminating the space. The kitchen area is visible, showcasing wooden accents and a modern design, enhancing the open concept layout.
Home in Montauk
4.88 out of 5 average rating, 207 reviews

Casa Bungo | Walk to Surf Lodge, Beach & Town!

TristaRating, 5 stars1 month ago
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

Guest favorite
The exterior of the house is seen from the front yard, featuring a white facade with black shutters and a red front door. Vibrant sunflowers grow in the foreground, complementing the green grass and surrounding trees.
Home in Montville
4.92 out of 5 average rating, 267 reviews

Casino Wine Down House

JenniferRating, 5 stars1 month ago
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.
Guest favorite
A large, fenced-in backyard features a wooden playground with a slide and climbing structure, surrounded by lush greenery. Soft grass covers the ground, creating a safe play area for children. Mature trees provide natural shade in this private outdoor space.
Home in East Hampton
4.93 out of 5 average rating, 109 reviews

Private & Pristine with Pool and Kid’s Playard

StephenRating, 5 stars4 months ago
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!
Top guest favorite
A light-filled living room features soft seating with a mix of blue and beige tones. A flat-screen television is positioned centrally, and a decorative area rug lies on the wooden floor. Large windows allow natural light to illuminate the space.
Home in North Fork
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars7 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Superhost
The living room features a blend of modern and mid-century design with a wood-planked ceiling. A large flat-screen TV is mounted on the wall above a wood-burning fireplace. A comfortable seating area includes a black leather couch and two orange chairs, complemented by decorative accents.
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars7 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Guest favorite
A welcoming living area features a large gray sectional couch with accent pillows, paired with a round coffee table. A light rug covers the dark wood floor, and a dining area with a small table and chairs is visible in the background. Natural light filters through sheer curtains.
Guest suite in Brooklyn
4.93 out of 5 average rating, 182 reviews

Affordable In-Law Apartment in Brooklyn, CT

OmarRating, 5 stars4 weeks ago
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!
Superhost
A two-story dark wood structure is surrounded by lush greenery. The backyard features a well-maintained lawn with patches of wildflowers and a shaded area highlighted by a red umbrella atop a deck. Tall trees provide a natural canopy, creating a serene outdoor setting.
Apartment in Brooklyn
4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars6 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 open floor plan reveals a studio space with hardwood flooring and an open beam ceiling. A spacious bed is placed against one wall, complemented by a light-toned nightstand. A circular fireplace is positioned near a blue accent chair and a dining table.
Cottage in Montauk
4.92 out of 5 average rating, 264 reviews

Montauk Oceanview Studio 6

MandyRating, 5 stars5 days ago
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!
Guest favorite
Home in Sag Harbor
4.85 out of 5 average rating, 262 reviews

Exclusive Sag Harbor Compound

WyattRating, 5 stars5 months ago
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

Destinations to explore