Family-friendly vacation rentals in Litchfield County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Litchfield County family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A bright living area features a comfortable seating arrangement and large windows that allow natural light to fill the space. A wood-burning stove is positioned in the corner, and an easel displays a vibrant painting. A plush rug adds warmth to the wood floor.
Home in Craryville
4.98 out of 5 average rating, 221 reviews

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson

DavidRating, 5 stars1 week ago
Three adults and a toddler spent four great days at Myrhah’s house in Craryville. I have very little to add to all the other enthusiastically positive reviews. They are totally accurate.I will note that one of us is a pastry chef who was at home in Myrhah’s kitchen. It’s stocked with quite a few good baking tools. Another member of our group is a 19-month old toddler who loved the toys and big airy spaces for play. We all enjoyed the home’s aesthetic and appreciated Myrhah’s responsiveness and warmth. I wished we could have stayed longer.
Guest favorite
A modern house is surrounded by trees with colorful autumn leaves. The exterior features a wraparound deck, and snow lightly covers the ground and plants. Clear blue skies enhance the peaceful outdoor setting, creating a serene atmosphere.
Home in Rhinebeck
4.92 out of 5 average rating, 236 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

BobRating, 5 stars3 weeks ago
We enjoyed our 2-night stay at Enrique's Rhinebeck home. It's out in the country, very peaceful, and very quiet at night. About an 8 minute drive to the charming town of Rhinebeck. We were out riding the rail trails during the day, but when at the house, really enjoyed the deck, hot tub, and screened porch (later at night when it got buggy). The kitchen is well appointed. Bedrooms and bathrooms are on the smaller side. Definitely would consider staying here again if ever back in the Rhinebeck area.
Guest favorite
An 8-person hot tub bubbles gently under the night sky, surrounded by trees. A scenic trail, lined with colorful lights, winds through the woods leading toward a well-lit deck. The inviting ambiance is set for relaxation and exploration.
Bungalow in Easthampton
4.92 out of 5 average rating, 504 reviews

The Creation Station

KennyRating, 5 stars3 weeks ago
Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.
Guest favorite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 323 reviews

Hilltop Hideaway Forest Villa on 13 acres!

JillRating, 5 stars2 weeks ago
Paula was an exceptional host! She was always quick to respond and answered my many questions, before and during our stay. The house was fantastic for entertaining. It’s spacious and we loved the art! We would have loved to enjoy the beautiful decks, but it rained during most of our visit. We made a fire instead! The house has Sonas and we loved having music. The large windows are great and so were all the views. It made me feel like I was in a treehouse! I would highly recommend this Airbnb and host.
Top guest favorite
A cozy living area features a stone fireplace with a warm fire, surrounded by wooden cabinetry and appliances. Brightly colored striped couches flank a wooden coffee table, while natural light streams in through a large window. Pendant lights add an inviting glow to the space.
Home in Ancramdale
4.94 out of 5 average rating, 142 reviews

Unwind in the country, stargaze in hot tub

OliviaRating, 5 stars4 months ago
What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.
Guest favorite
The charming country house showcases a light-colored exterior with symmetrical windows and a covered porch. Lush greenery surrounds the entryway, providing a welcoming feel. The roof features a gabled design, and a garage is positioned on the left side of the image.
Home in Elizaville
4.86 out of 5 average rating, 102 reviews

Peaceful Hudson Valley Retreat House with HOT TUB!

RossRating, 5 stars2 weeks ago
We had a great and easy stay for a quick upstate weekend! The house was clean, cute, and accommodated our family of 7. We unfortunately didn’t get to utilize the outdoors because of the weather. Would definitely recommend this house!
Guest favorite
A red guest house is nestled among tall trees in a woodland setting. Large windows allow natural light to fill the interior, while the surrounding forest provides a serene backdrop. Leafy undergrowth and a carpet of dried leaves cover the ground in front of the house.
Home in Red Hook
4.88 out of 5 average rating, 234 reviews

Wooded Retreat w/ Hot Tub and Trout River

DanicaRating, 5 stars1 week ago
Just what we needed for a relaxing weekend. Place was clean and comfortable. Situated in the woods- scenic, quiet and relaxing with the sound of the creek down below. Rainy weekend but it was dreamy looking out the large floor to ceiling windows. Highly recommend this place if youre looking for a quiet getaway. Rhinebeck Village and Red Hook shops are within 20-30 min drive.
Guest favorite
A well-equipped kitchen includes wooden cabinets and essential appliances, facing a cozy dining area with a table and chairs. The living space features a comfortable seating area with a soft couch and a television, while natural light filters through the window treatments.
Guest suite in Guilford
4.96 out of 5 average rating, 157 reviews

Bright, Cozy Apartment in Guilford

KarenRating, 5 stars7 months ago
The home was absolutely gorgeous and peaceful. It's exactly as described but even more spacious than I expected. They put a lot into making guests feel welcome, including prompt communication, a quick walk through to explain where things are, numerous suggestions for the surrounding area, and even a tray of welcome cookies! I came for a 50k trail race, so the hot tub was a perfect added bonus. I HIGHLY suggest booking this property, and I'll definitely be back to spend some time at the beach.

Family- and pet-friendly home rentals

Guest favorite
A serene lake is surrounded by lush green hills, reflecting the clear blue sky. The water is calm, with a small rowboat visible in the distance, adding to the tranquil outdoor setting.
Home in Ancram
4.99 out of 5 average rating, 181 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

AdelyaRating, 5 stars1 month ago
The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!
Top guest favorite
A two-story house showcases a welcoming front porch with hanging flower pots. The lawn is well-kept and bordered by garden beds. The exterior features a blend of white and muted green siding, with prominent green shutters on the upper windows.
Home in Millerton
4.9 out of 5 average rating, 156 reviews

The 1913 House, book 6 days get the 7th free.

BenRating, 5 stars1 week ago
My wife and I had a great time. Amazing house right outside of town. Huge yard which our dog loved! Hopefully we will be back.
Top guest favorite
The exterior of a two-story colonial home is framed by lush greenery, presenting a manicured lawn. A charming porch with steps invites guests, while a brick chimney rises from the roof, adding character to the light-colored siding.
Guesthouse in South Salem
4.94 out of 5 average rating, 283 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

AlicjaRating, 5 stars1 month ago
We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!
Guest favorite
A Mediterranean style house is showcased against a backdrop of rolling hills and the Hudson River. The exterior features multiple windows, and a stone chimney rises from the roof. The expansive landscape is highlighted by autumn foliage, creating a vibrant setting.
Home in Garrison
4.93 out of 5 average rating, 162 reviews

Hudson Valley Mountaintop Riverview

JacquelynRating, 5 stars2 weeks ago
Mahmoud was a wonderful host. Very responsive, pleasant, and helpful. His home and the views were spectacular, and the koi pond was beautiful. It’s a great location to stay while visiting West Point, as it’s a quick drive across the Bear Mountain Bridge. Our large group felt comfortable and welcomed. One of the bedroom descriptions could have been listed a little clearer because you need to pass through the master bedroom to get to it. Luckily our family was ok with that. We would stay again.
Top guest favorite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars5 days ago
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!
Top guest favorite
The exterior of a modern wooden house is surrounded by lush greenery. Large windows allow natural light to fill the interior. A neat lawn leads to the entrance, which is framed by manicured bushes and trees in the background.
Home in Millbrook
5 out of 5 average rating, 115 reviews

Stunning Views, Light and Open - The Beech House

BobbiRating, 5 stars3 weeks ago
We lived in the Hudson Valley before retiring to Maine. For the past 4 years, Sarah and Jonathan’s home has provided the perfect spot for return visits with family and friends and a comfortable place away from home. The house is tastefully decorated and provides all that we require for an extended stay. The kitchen is well appointed with utensils, dishware, pans, and a large assortment of appliances. A special feature in the home is the lower level room with a huge wrap-around couch, large screen tv and toys for the kids. In addition, the grounds are beautiful. The outside deck allows for time to enjoy the gorgeous view and the large yard is fun for romps with our little Havanese. Being close to the town is an added bonus: The Tribute Gardens, Marona’s Market, the little French restaurant (Cafe Les Beaux), Stewart’s for ice cream, The Merritt Bookstore + Toystore, various antique shops are places we frequent. Innisfree Gardens and Dover Stone Church are nearby. We love it here!
Top guest favorite
A spacious studio apartment is displayed with natural light streaming through large windows. A comfortable narrow futon and a cozy seating area are visible, along with a dining table surrounded by wooden chairs. A door leads to the private deck, enhancing the overall openness.
Apartment in Sandisfield
4.92 out of 5 average rating, 235 reviews

Sunny Berkshire Studio Apartment

AntonRating, 5 stars9 months ago
Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again
Guest favorite
A welcoming living area features a spacious sectional sofa adorned with accent pillows. A coffee table with a glass top, displaying a small vase of flowers, sits in the center. Light filters in through sliding glass doors, illuminating the wood-like flooring.
Apartment in Carmel-by-the-Sea
4.87 out of 5 average rating, 298 reviews

Private space, with yard

EmilyRating, 5 stars2 weeks ago
We had a great stay here as we explored nearby things (the Chuang Yen Monastery was delightful!) and visited some favorite spots. The weather was a little dreary when we were there, otherwise we would have made good use of the beautiful outdoor space. It was the perfect place for us to relax after our adventures every day—very quiet, very comfortable, clearly-written instructions for everything. We would be very happy to return!

Family-friendly home rentals with a pool

Top guest favorite
A swimming pool is set in a lush green yard, surrounded by trees and flowering plants. Comfortable lounge chairs are positioned nearby, while a large rock adds a natural element to the pool area. The property's main house stands in the background, completing the inviting scene.
Barn in Bethel
4.98 out of 5 average rating, 237 reviews

Escape to a Restored New England Antique Milk Barn

GavinRating, 5 stars2 weeks ago
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.
Guest favorite
A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.
Home in Stormville
4.94 out of 5 average rating, 179 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars6 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
Top guest favorite
An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars7 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Top guest favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Superhost
A spacious cottage is set against a backdrop of trees, with a rectangular heated pool highlighted in the foreground. Several light green lounge chairs are arranged around the pool area. A wooden deck extends from the house, where shaded seating is visible.
Home in Washington
4.89 out of 5 average rating, 27 reviews

ShrinkMapBestTown Washington "Shearer" PoshPadsCT

LaraRating, 5 stars10 months ago
We had a wonderful long weekend stay! Steve was an excellent host, who was very hospitable and responsive, allowing us flexible check in and check out, leaving a thoughtful welcome gift and sending us recommendations for things to do in the local area. We ended up hiking, wine tasting, visiting local restaurants. The home was great for our two kids (12 year old and 3 year old) and we made use of the pool every day! Wish we could've stayed longer but it was the perfect city getaway.
Top guest favorite
The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.
Cabin in Red Hook
4.96 out of 5 average rating, 352 reviews

Modern Upstate Cabin, near Rhinebeck NY

EllieRating, 5 stars2 weeks ago
We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.
Guest favorite
An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.
Apartment in Glastonbury
4.89 out of 5 average rating, 438 reviews

Quiet 2 bed room apt w/ private entrance.

JoshRating, 5 stars3 weeks ago
Alice’s place was great! We’ll be back again for sure.

Destinations to explore