
Kid-friendly holiday rentals in Westbrook
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Top-rated family-friendly rentals in Westbrook
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Kid-friendly house rentals

“The Answer” Your Unique, Tidal, Riverfront Escape
Booked my parents a staycation here, so writing on their behalf: they LOVED it!! After they got back they kept raving about how tranquil and beautiful the place was. Also every little detail that Ellie and Tower provided was so intentional and thoughtful - including a bday note/basket for my parents and “just in case” products (which my mom said was amazing bc she forgot her toothbrush). Plus, the place was spotless. Overall, 10/10 highly recommend and I hope to go there in the future!! 😊

Cornfield Point Beach House View
Chloe's home was perfect for our stay as we wanted to be near my son in Old Saybrook. She was responsive and accommodating with my questions and needs always getting back to me right away. Check in was easy and I received emails all along the way which was helpful as I am a first time airbnb person. The home was immaculate with everything as it said it would be. I would definitely stay again and recommend this home.

Amazing 2BR Riverfront Gem
Hard to believe how close to the highway this is. It’s so peaceful and serene. You look out onto a marshy body of water and can watch the ducks and ducklings and a resident crane. It’s lovely. Yet 3 minutes from a supermarket to stock up on supplies. Would definitely recommend.

Water Views and Walk to Beach
We were in Connecticut for our nephew's graduation from Yale. While searching for a house that could accommodate 8 people, I came across this beautiful home. When arriving and walking into the house, it exceeded all of my expectations. It was absolutely gorgeous and only a few steps to the beach. Our family could not stop talking about how exceptional the house was. The little town of Old Saybrook was so cute as well. I would highly recommend this amazing house to anyone that is staying in the area. Trust me, you will not be disappointed.

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

The Cottage
This was the perfect place to stay for our weekend get away. It’s a great location close to a lot of restaurants, shopping, and beaches. We had everything we needed and the beds were very comfortable. We would definitely stay there again.

Mid-Century 4 bedrooms with Water View & Access
We had a wonderful weekend at Aude's home in Essex. The setting was beautiful and the house itself was immaculate. It is a 7 minute drive to the center of town, which was convenient. The host was very responsive and quick to fix any concerns we brought to her attention. I would definitely return to this Airbnb!

Plan your summer getaway! 3 Night Minimum
Unique mid-century mod house design with glass walls viewing the deck & garden, comfortable furniture, fully equipped kitchen, short safe walk to the beach & nearby playground. Responsive hosts. Pristine bathrooms & plush linens. Sauna! Parents of young children may want to block access to the spiral stairs & loft. Older kids will want to hang out in the cool loft! Also perfect for yoga… Great food & brews at nearby Haywire Burger Bar! We plan to return. Thank you Melissa & Patricia
Family-friendly apartment rentals

The Federal Suite at the Wisteria Rest
Very nice apt and perfect for a quick weekend getaway.

Private apartment in historic Old Lyme mansion
Holly's home is a spectacular antique in a lovely area of Old Lyme. The apartment is on the third floor, up a gorgeous curving staircase, and is very comfortable and spacious, with high ceilings and cozy furniture. We were in town for a funeral and so didn't have a chance to enjoy just hanging around, but we did manage to have coffee twice at Long River farm market, as well as dinner at the Hangry Goose. Both are great and less than a mile from the house. This apartment is a really unique stay, and it reminded me of an apartment in Paris.

Charming Chester Retreat - Cottage
Wow!!! This is the nicest airbnb I have ever stayed in. The property is beautiful and peaceful, surrounded by trees with lots of privacy. The cottage itself is immaculate (I’m very particular about cleanliness). The dining area is stunning with skylights and beautiful trees outside and great light! The hosts were also so welcoming and friendly, they included so many nice touches for my baby including a pack and play/travel crib, diaper changing area, and toys! I hope to stay here again every time we come to this area!

Spacious Cozy Guest Suite
Radim was the perfect host. Responsive, friendly and knowledgeable about the area we were going to. Would definitely recommend a stay at Radim’s place.

Guilford Guest House- private studio apartment
I loved Suzanne’s place! I was in town for a wedding at the Guilford Yacht Club and her listing is the perfect location. It’s a really well done studio. Suzanne is kind and quick to respond. Also, she let me check out pretty late which was cool.

Peaceful apartment on 3.5 acres w/ Artist studio.
The house was perfect for us, just a couple! It felt cozy and the artist studio/pool table was perfect for entertainment! Host was proactive with instructions and was super friendly! Would stay here again!

Lovely Garden-Level Apartment in Heart of Town
Lovely town and environment. Very spacious and fully equipped apartment. The two bedrooms are separated from each other by the big kitchen, a little reading room and the living room…so good privacy. Two TVs. Comfy beds! The small town is an easy and pleasant walk. It’s a ground floor apartment under the owners house, so be prepared for the patter of little dog feet above. We did not see the owners but communication was terrific. Great place to stay in the vicinity.

Brand New Direct Lakefront - Panoramic Sunsets
Beautiful home with beautiful surroundings. It was the perfect layout for our family to gather together. RV park was quiet and peaceful. Kevin’s tiny homes that surround this house look adorable! My next solo trip will be in one of those:)
Family-friendly apartment rentals

CASiNO, Spa, Hot Tub, Pool, King bed, sauna
I am very familiar with the villas there so the layout is very similar to the one my parents bought. I think it was very nice to have the keypad to get in and out and everything was clean and it was very easy communicating with Kim.

New Britain "Joy of Small Space" Condo
Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!

Entire place to yourself Cromwell/Middletown Line
Great apartment! Furniture is comfy. Kitchen is fully stocked. Neighborhood is peaceful. During my stay the cutting boards were stored between the microwave and wall (took me a day to find them)

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

The Vacay Villa
This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.

Peaceful Oasis steps from Mohegan Sun
We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.

The N-V ...The Spa at the Norwich Inn.
We stayed in town for an event at Mohegan Sun. The flexible check in was helpful as we got in late at night. The place was clean and welcoming.
Quick stats about holiday rentals that are kid-friendly in Westbrook
Total rentals
30 properties
Nightly prices starting at
₹8,579 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Woodmont Beach
- Amagansett Beach
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Blue Shutters Beach
- Sunken Meadow State Park
- Bushnell Park
- Sherwood Island State Park
- Bayview Beach