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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, 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.
Superhost
The exterior of the resort showcases a distinctive architectural style with a central tower and a mix of stone and wood materials. A landscaped area features a pool and a gazebo, surrounded by neatly arranged trees and shrubs. Parking spaces are visible in the foreground.
Apartment in Newport
4.79 out of 5 average rating, 14 reviews

Newport Resorts

AnantRating, 5 stars7 months ago
Andrew was an excellent host and this was the perfect place for a family. We have been coming to Newport for years and this is one of the best places we have stayed. Highly recommend!
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, 73 reviews

Family Friendly Springs Beach House

MichelleRating, 5 stars1 week ago
Fantastic stay/fantastic hosts! My adult children and I spent a great weekend hosted by David and Abby. Their place was perfect for us and very comfortable. David reached out and described check in and proactively answered any questions we would have had. We were there in cold weather but I will earmark it for a warm weather stay as it has so many appealing summer amenities! We will stay again for sure.
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
Villa in East Hampton
4.95 out of 5 average rating, 44 reviews

Luxury| Pool| GOLF Sim| HotTub| MovieTheater| Arcade

CharlotteRating, 5 stars5 days ago
We had a lovely stay this April. House was spotless and newly refurbished. Pool area great (early in season so braved a cold plunge!!!) and appreciated the separate hot tub too. Pool furniture all brand new and special mention of the best kitted out games room I have ever seen! Location great. Very quiet but short car ride to East Hampton proper. Sammi’s beach a 10 min walk away. A fantastic stay and would not hesitate to recommend to others.
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.

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.
Top guest favorite
The exterior of a classic New England-style home is displayed, featuring a mix of wooden shingles and siding. The structure has multiple windows, providing a view of the inviting entrance. A tranquil atmosphere is accentuated by the surrounding trees and clear blue sky.
Home in Newport
4.94 out of 5 average rating, 113 reviews

Peleg Barker House. Spacious & Family Friendly!

MichaelRating, 5 stars3 months ago
We had a wonderful off-season weekend at Jenny’s place. It’s a beautiful home that is well appointed, which made it easy to settle in. The house is also in a prime location in downtown Newport. Being mid-January, it was nice to have a short walk to many great restaurants and shops. We look forward to coming back!
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!

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.
Superhost
Home in New London
4.91 out of 5 average rating, 178 reviews

Sunset Oasis 1 @ Ocean Beach: $1Mil View 6 Queen

DanielRating, 5 stars4 months ago
Great spot, would definitely stay again.
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!
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
4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

JulieRating, 5 stars5 months ago
Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

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