Family-friendly vacation rentals in Middlebury

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Middlebury family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A cozy sleeping area is featured with a spacious bed adorned with soft pillows. Natural light filters through sheer curtains, illuminating warm wooden walls. A small TV and a decorative chair provide additional comfort, while a touch of greenery enhances the inviting atmosphere.
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars3 months ago
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.
Guest favorite
A wooden cabin is nestled among tall trees, featuring a spacious front deck with wooden railing. The sloping roof and large windows contribute to a welcoming exterior, framed by lush greenery and undergrowth. Sunlight filters through the trees, enhancing the serene woodland setting.
Cabin in Keene
4.96 out of 5 average rating, 193 reviews

Honeymoon Cabin with Jacuzzi Tub

SummerRating, 5 stars1 month ago
We came up for a few nights to elope in the mountains with our two dogs. Meghan was so accommodating. This is our second time at this cabin but plan on making this our go to vacation spot when we come to Lake Placid!
Guest favorite
The spacious living area features a large sectional sofa and a coffee table made from natural wood. A flat-screen television is mounted on the wall. Sliding glass doors lead to the outdoor space, while wooden floors and a vaulted ceiling create a warm ambiance.
Cabin in Starksboro
4.88 out of 5 average rating, 284 reviews

Charming getaway tucked away in the Green Mtns

TraceyRating, 5 stars1 month ago
Not sure if it was the mattress, the sheets and quilt, the pillows, the Vermont woods, Vermont fresh air, or the rain hitting the roof… maybe all of it… but, my husband and I have not slept so well in… maybe EVER! Rob’s home is super comfy and dog friendly. The hot tub is a nice feature and works wonderfully. If you are looking for a quiet, peaceful location for your visit, this hits all the marks. Sitting outside with your morning coffee is a treat. If weather doesn’t cooperate, recommend sitting in the den in front of the picture window. Our old dog truly appreciated exploring the fenced yard, and we loved allowing him off off-leash. Great place to stay!
Guest favorite
A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.
Yurt in Randolph
4.95 out of 5 average rating, 434 reviews

Lower Yurt Stay on VT Homestead

AlinaRating, 5 stars1 week ago
Beautiful spot to relax, reconnect and leave refreshed! We enjoyed everything about our stay, especially the sauna, living pool, and hike to the yurt! We would love to return, thank you for sharing such a peaceful place with us, it was exactly what we needed.
Guest favorite
A serene forest scene captures a shallow stream flowing among bare trees, with a gentle sunlight filtering through. In the foreground, a colorful insulated cup with a giraffe design rests on a rock, surrounded by autumn leaves, adding a touch of whimsy.
Apartment in Hinesburg
4.93 out of 5 average rating, 288 reviews

Hilltop Haven

LeahRating, 5 stars1 week ago
We had a wonderful stay at the Monty's place -- the apartment was well stocked with many thoughtful items, the area is very peaceful and near to outdoor activities, and the hosts were friendly and responsive. Would definitely stay again! Thank you!
Superhost
The exterior of a spacious home is set against a bright blue sky with fluffy clouds. Flowering plants and grass surround the entrance, creating a welcoming outdoor space. The architecture features various slopes and shapes, highlighting the unique design of the residence.
Guest suite in Jericho
4.74 out of 5 average rating, 293 reviews

Apartment, comfy and cozy with kitchen/gas fire

DavidRating, 5 stars1 week ago
We really enjoyed this place! The property is beautiful. The pool looked really clean and well cared for (but we didn't have a chance to use it). The supplied linens and especially the bath towels were great. This certainly will be on our list the next time are in VT.
Top guest favorite
The exterior of the chalet is showcased, highlighting a welcoming entryway with a wooden deck and a pathway made of stones leading towards the lush greenery. The backdrop features rolling mountains under a clear blue sky, enhancing the natural setting.
Home in Wilmington
4.98 out of 5 average rating, 289 reviews

Breathtaking View, Hot Tub, Sauna, Pets Ok!

MarkRating, 5 stars4 days ago
We completed the lake placid 9er hike on our stay. Great location with all hikes less than 20 min away (some less than 10). Spectacular view and incredible kitchen. Hot tub and sauna were great amenities for recovery from long days hiking. Place is as advertised and you cannot beat the view of the mountains. Highly suggest going to the hungry trout restaurant. Only a few minutes away, much closer than downtown lake placid and the food/service was great. Highly recommend this rental and hope to be back next year to begin the 46er.
Top guest favorite
A newly constructed cabin with a warm wooden exterior is surrounded by lush greenery. The gravel driveway leads to the entrance, framed by tall trees. A decorative star shape is featured above the front door, creating a quaint focal point.
Cabin in Ripton
5 out of 5 average rating, 106 reviews

#7 - Hemlock Hideaway Cabin

ChrisRating, 5 stars3 months ago
Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.

Family- and pet-friendly home rentals

Guest favorite
The exterior of the cabin is shown, featuring a deck with seating and a grill. Surrounding grass areas are well maintained, with tall trees in the background. The structure's two distinct rooflines enhance its rustic charm.
Cabin in North Hudson
4.82 out of 5 average rating, 293 reviews

Schroon River Cabin

SarahRating, 5 stars4 weeks ago
Bob and Joan’s cabin was absolutely spectacular. Overall this place is the perfect mountain getaway! This place has all the amenities you could need, prime commute to surrounding ADK regions, and let’s not forget the breathtaking views. This place exceeded our expectations and was exactly what we needed for a get away to the mountains with the dog. Bob was an amazing host and we look forward to coming back, as well as passing along this gem to friends and family to also book with Bob & Joan!
Guest favorite
A secluded cabin is nestled among trees and foliage during autumn. Vibrant fall leaves cover the ground, and a variety of evergreens provide a natural backdrop. The cabin features a large front porch, allowing for a peaceful connection with the surrounding wilderness.
Cabin in Woodstock
4.95 out of 5 average rating, 200 reviews

Hideaway Cabin by the Stream on 27 Acres

JenniferRating, 5 stars3 weeks ago
Our stay was incredible! The view by the stream was amazing, everything was so peaceful and perfect. Inside the cabin was exactly what we expected, very homey, everything we needed. We loved the walls lined with books! Kevin was very attentive towards what we needed - it stormed all day Saturday and he brought a second heater for us because the temperature dropped, which with that and the gas fireplace, kept the place perfectly warm and comfortable. He was also very accommodating in allowing us to stay an extra night since our plans of hiking all weekend were thwarted by the rain. We went for my husband's 40th birthday and i couldn't have picked a better place to get away from the stress of life. We plan on going back for sure!
Guest favorite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville
4.9 out of 5 average rating, 909 reviews

Moon Valley Country Retreat no clean fee pets yes

ArndRating, 5 stars5 days ago
Great place to stay. Quiet and secluded. Has everything you need. Great host.
Top guest favorite
A rural house is framed by mature trees, displaying vibrant autumn foliage. The spacious yard features a mix of greenery and colorful bushes, with a clear blue sky overhead. The house is set back from the road, offering a peaceful country setting.
Guest suite in Plainfield
4.95 out of 5 average rating, 414 reviews

House in beautiful rural Plainfield

NykkiRating, 5 stars1 week ago
My daughter and I had a wonderful stay. Gail and her husband were the nicest hosts. We had some great chats. The area is absolutely beautiful and peaceful.
Superhost
An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.
Chalet in Stockbridge
4.84 out of 5 average rating, 159 reviews

Vermont Chalet

VanessaRating, 5 stars2 weeks ago
Had a great time at Janie’s chalet. It was peaceful and quiet. Janie was a great host and very attentive.
Top guest favorite
A log home is illuminated by exterior lights, highlighting its natural wood texture. The path of stone leads to the entrance, framed by manicured grass and logs. Adirondack chairs are positioned on the porch, creating a welcoming outdoor space with a fire pit nearby.
Home in Wilmington
5 out of 5 average rating, 121 reviews

Wilmington Range Log Cabin on the AuSable River

MarkRating, 5 stars1 week ago
Beautiful cabin in the woods that isn’t too far from anything but feels isolated just the same. Terrific base of operations to access many trailheads, Lake Placid and Saranac Lake. Restful and low maintenance stay. We would recommend and visit again.
Superhost
A spacious deck features wooden flooring and railing, surrounded by trees. Two wooden lounge chairs face a breathtaking view of the Green Mountains, providing an open space to relax and enjoy the natural scenery.
Home in Rochester
4.91 out of 5 average rating, 296 reviews

Mountain Home ready for you!

IvanRating, 5 stars3 months ago
This place was great. Very spacious and comfortable with beautiful views and sunsets! 10/10
Top guest favorite
A cozy log cabin interior is illuminated by natural light from windows. A comfortable blue couch faces a stone fireplace. Above, a sleeping loft is accessed by sturdy wooden steps and bordered by wood railing. Maple hardwood floors and bookshelves add warmth to the space.
Cabin in Warren
4.97 out of 5 average rating, 132 reviews

Stetson Hollow Cabin by Stetson Brook

MicheleRating, 5 stars2 months ago
Adorable, cozy cabin 10 minutes from Sugarbush ski resort. Very relaxing atmosphere. Well stocked with linens and firewood. Jill left us a little delicious treat. Would stay here again

Family-friendly home rentals with a pool

Top guest favorite
A clear blue pool is surrounded by a stone patio and lush green landscaping. Two lounge chairs are positioned nearby. A flagpole is visible in the background, and a hanging planter adds a touch of color.
Guesthouse in Ticonderoga
5 out of 5 average rating, 213 reviews

Chilson Brook Alpacas

MelissaRating, 5 stars1 day ago
Beautiful stay with incredibly kind hosts! Pool was lovely and the alpacas were so much fun to pet. Would love to return
Guest favorite
An outdoor pool is surrounded by a concrete patio and well-maintained grass. Several lounge chairs are positioned around the pool, offering space for relaxation. The pool's clear blue water reflects the greenery of the trees that encircle the area.
Condo in Warren
4.87 out of 5 average rating, 199 reviews

Ski In/Ski Out with upgrades!

KarenRating, 5 stars2 months ago
My husband and I stayed here to do a few days of spring skiing at Sugarbush. The location is perfect, a short walk to the slopes when there's snow. Two-minute drive to resort if snow is sparse. Sugarbush is a huge resort and has many options for all skills of skiing. The condo was spotless and had a full kitchen with plenty of pots and pans, etc. It was very comfortable and also had a selection of books and games to choose from. Host was very responsive and gave perfect instructions. Thank you!
Top guest favorite
A breathtaking view showcases the sun rising above the horizon, casting warm orange and yellow hues across the sky. The silhouette of Camel's Hump is visible in the distance, framed by softly illuminated clouds. The scene evokes a sense of tranquility and natural beauty.
Apartment in Barre
4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

JenniferRating, 5 stars3 months ago
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!
Top guest favorite
An indoor pool area features clear water reflecting the wood-beamed ceiling overhead. Large windows allow natural light to illuminate the space, highlighting the smooth concrete poolside. A few lounge chairs are visible along the edge, offering a place to relax.
Condo in Warren
4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars3 months ago
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy
Guest favorite
This inviting living area features a gray sectional sofa, a wooden coffee table, and a comfortable chair. Large windows provide natural light and views of the surrounding mountains. Soft curtains frame the windows, and a gas fireplace adds warmth to the space.
Home in Stowe
4.91 out of 5 average rating, 141 reviews

Mountain Side Studio Spruce Peak Lodge | 1332

CourtneyRating, 5 stars3 months ago
Great studio and location. View of Stowe resort mountain. Easy to get around the resort. Unit was clean and as expected.
Superhost
A dining area is set with a wooden table adorned with plates and glassware, complemented by a stylish chandelier overhead. In the background, a comfortably furnished living area features a sofa and a smart TV, creating a welcoming environment.
Condo in Killington
4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

RodneyRating, 5 stars4 months ago
Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.
Superhost
An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars4 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Superhost
A seasonal outdoor pool is surrounded by a fenced area, featuring lounge chairs and a colorful hammock. Lush green trees provide shade, while sunlight reflects off the clear water. A nearby cottage is visible in the background, adding to the tranquil setting.
Cottage in Stowe
4.77 out of 5 average rating, 241 reviews

Cute Cottage - Poolside - Minutes To Activities

ChrisRating, 5 stars2 months ago
Linda was a fantastic host, and her home was even better than listed. The cabin was a good size for our family of four + dog; the 2 bed / 2 bath arrangement allowed for good privacy when needed. The fireplace was great for apres and winding down at night. Location is a nice mix of seclusion (off the Mountain Rd), but close to everything.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore