Family-friendly vacation rentals in Westerly

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Westerly family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Norwich
4.84 out of 5 average rating, 150 reviews

Villa Flora @ Norwich Inn & Spa

DebraRating, 5 stars7 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 favourite
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 favourite
Home in North Fork
4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars5 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 favourite
Home in Stonington
4.97 out of 5 average rating, 220 reviews

Perfect New England Getaway has a pool/ hot tub

DanaRating, 5 stars1 month 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 favourite
Cabin in North Fork
4.86 out of 5 average rating, 102 reviews

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

AllisonRating, 5 stars3 months ago
We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.
Guest favourite
Home in East Hampton
4.94 out of 5 average rating, 161 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

RichardRating, 5 stars1 month ago
Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!
Guest favourite
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 favourite
Villa in Norwich
4.89 out of 5 average rating, 400 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

DevinRating, 5 stars2 weeks ago
Over all amazing experience!! Very relaxing and helps you enter a peaceful state of mind. The villa was comforting and clean. The hot tub is mostly private and no one there but when there the people in the neighborhood are lovely and give you plenty of recommendations locally. I highly recommend for a nice relaxing getaway!!

Family- and pet-friendly home rentals

Guest favourite
Condo in Newport
4.92 out of 5 average rating, 659 reviews

Boutique Hotel Special pricing available

MichaelRating, 5 starstoday
I've been to Newport many times on day trips, but never for an overnight. My partner had never been to Rhode Island, so I thought it would be fun to stay in downtown Newport and explore while also visiting with family in Providence. Pelham Court could not be more convenient. Perfectly located across from the waterfront, the property is safe, secure and convenient. A big plus is off-street parking. Our one-bedroom unit was awesome. Spacious, well-appointed and very comfortable. Although we were in the middle of everything, we had peace and quiet. The Pelham Court team were awesome: responsive, friendly, helpful and ready to offer local insights, including when we just wanted to stay in and order pizza. I would highly recommend this as your Newport getaway that's close to everything. Great accommodations, great location, and great professional support.
Guest favourite
Home in Hopkinton
4.88 out of 5 average rating, 122 reviews

Large estate with pond near beaches

SaraRating, 5 stars5 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 favourite
Guest suite in Brooklyn
4.92 out of 5 average rating, 183 reviews

Affordable In-Law Apartment in Brooklyn, CT

OmarRating, 5 stars1 month 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!
Guest favourite
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars8 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 favourite
Home in Newport
4.91 out of 5 average rating, 164 reviews

⚓️ Top Notch Newport Location! SuperHost! 🏡

DaveRating, 5 stars1 week ago
The location is absolutely perfect, just a short walk away from shops, restaurants, and the water. The hosts were very responsive when needed and even helped a friend out when they left something at the house. The house itself fit our needs very well. It was very clean and comfortable and had everything we needed to enjoy our time in Newport. I would and hopefully plan to stay at this property again. Thank you, Sean and Erica, for everything!
Guest favourite
Home in North Fork
4.91 out of 5 average rating, 104 reviews

Cozy Farmhouse Retreat in North Fork, NY

MarisaRating, 5 stars4 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 favourite
Apartment in Middletown
4.88 out of 5 average rating, 301 reviews

3 bedroom near Wesleyan, downtown

BangheeRating, 5 stars1 month ago
Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!
Guest favourite
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 favourite
Home in Montville
4.92 out of 5 average rating, 268 reviews

Casino Wine Down House

MarkavaRating, 5 stars1 week 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 favourite
Home in East Hampton
4.93 out of 5 average rating, 110 reviews

Private & Pristine with Pool and Kid’s Playard

ChrisRating, 5 stars2 weeks 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 favourite
Home in North Fork
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars8 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars8 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Superhost
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 favourite
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!
Superhost
Guesthouse in Shelter Island
4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

FernRating, 5 stars7 months ago
John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars1 week ago
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

Quick stats about vacation rentals that are family-friendly in Westerly

  • Total rentals

    210 properties

  • Nightly prices starting at

    $83 CAD before taxes and fees

  • Total number of reviews

    8K reviews

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

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