Family-friendly holiday rentals in Middlebury

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Popular amenities for Middlebury family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
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!
Top guest favourite
Guest house 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 favourite
Cabin in Starksboro
4.88 out of 5 average rating, 285 reviews

Charming getaway tucked away in the Green Mtns

EbonyRating, 5 stars2 days ago
I booked a last minute escape from the city and Rob’s mountain getaway was exactly what I needed. The home was both welcoming & comforting with enough blankets to keep me & our furry one warm and cozy. The stocked coffee bar & equipped kitchen made the mornings a breeze. Tucked away in the peaceful mountains of Vermont, stargazing takes on a whole new meaning while in the amazing hot-tub Rob has on the property. The weather was too variable for us to utilize the lovely fire pit but that’s what the winter time is for. Still peaceful to sit up in the ski chairs and enjoy the scenery. We even saw a hummingbird! All in all, Rob is an amazing host with a home filled with so much character and charm. The local restaurant recommendations were all a hit! It’s a quick 30-40 minute drive to Burlington We even extended an extra day because we enjoyed our time so much and Rob was quick to reply and enthusiastic in all communications. 10/10 will stay again and highly recommend!
Guest favourite
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 favourite
Flat 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
Guest suite in Jericho
4.74 out of 5 average rating, 293 reviews

Apartment, comfy and cozy with kitchen/gas fire

DavidRating, 5 stars2 weeks 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 favourite
Home in Wilmington
4.98 out of 5 average rating, 289 reviews

Breathtaking View, Hot Tub, Sauna, Pets Ok!

MarkRating, 5 stars6 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.
Guest favourite
Chalet in Stowe
4.95 out of 5 average rating, 348 reviews

Contemporary Chalet in Stowe

DarleneRating, 5 stars4 weeks ago
We enjoyed celebrating our anniversary in this home. Kitchen was easy to cook in. Lots of creature comforts, extra blankets, towels and all of the essentially we needed for three relaxing nights. We visited in late spring but hope to return and enjoy the view in another season. While there were only two of us, the home can accommodate a larger group comfortably.

Family- and pet-friendly home rentals

Guest favourite
Cabin in North Hudson
4.82 out of 5 average rating, 293 reviews

Schroon River Cabin

SarahRating, 5 stars1 month 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 favourite
Tiny home in Duxbury
4.97 out of 5 average rating, 279 reviews

Tiny House at Camp Comyns

VeronicaRating, 5 stars1 month ago
We loved how she had breakfast items stocked for us! The beds were so comfy and the tiny house was so cute! Enjoyed our stay!
Guest favourite
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 favourite
Guest house in Granville
4.9 out of 5 average rating, 910 reviews

Moon Valley Country Retreat no clean fee pets yes

GabrielRating, 5 stars2 days ago
This is a wonderful place to stay. It’s very clean and the hosts have prepared for everything. It feels like your own cabin in the woods. Plus there are so many activities in a short distance of the place.
Superhost
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.
Guest favourite
Cabin in Elizabethtown
4.87 out of 5 average rating, 852 reviews

Bell Crest Cabin, 1 bedroom

MichaelRating, 5 stars1 week ago
An absolute bargain and just perfect. We will be back for sure! Super responsive host.
Top guest favourite
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.
Top guest favourite
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 favourite
Guest house in Ticonderoga
5 out of 5 average rating, 213 reviews

Chilson Brook Alpacas

MelissaRating, 5 stars3 days ago
Beautiful stay with incredibly kind hosts! Pool was lovely and the alpacas were so much fun to pet. Would love to return
Guest favourite
Apartment 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!
Guest favourite
Guest suite in Killington
4.95 out of 5 average rating, 146 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

DiannaRating, 5 stars3 days ago
all around the house was so pretty! flowers and felt like you're in the middle of the forest, the house standing on a small hill and the only exit is through one driveway on a mini bridge, which is very cute and secluded. The only downside is sooooo many mosquitoes, but thats honestly everywhere especially if you're in the forest. This place gives off you're visiting your grandparents home, which felt very nice and refreshing especially since we're from a rowdy city.
Top guest favourite
Flat 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 favourite
Apartment 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
Top guest favourite
Home in Stowe
4.95 out of 5 average rating, 108 reviews

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak

BrianRating, 5 stars1 month ago
This place was perfect for our family of three for a long weekend. The room had everything we needed and the views of the village from the balcony were amazing. Lots to do in the village and plenty more just a short drive down the road to Stowe. We’d love to come back in the summer when there are more outdoor activities available.
Superhost
Apartment in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars5 months ago
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.
Guest favourite
Apartment in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars3 months ago
Great spot near the mountain. nice community pool and hot tub.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹7,740 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

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