
House holiday rentals in Middlebury
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Top-rated house rentals in Middlebury
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Holiday rentals for every style
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Popular amenities for Middlebury house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
We really enjoyed our stay at this super cute Airbnb! The location was perfect — just a quick drive to everywhere we wanted to go, which made exploring the area super convenient. The space itself was clean, cozy, and had such a charming vibe. One thing to note is that there’s no AC, which I didn’t realize ahead of time. It wasn’t a dealbreaker by any means, but as a cold sleeper, it was a bit warm for me in June — just something to keep in mind depending on the season. Overall, it was a lovely place and a great spot for a getaway!

Lux Alpine Studio Ski In Ski Out. Spruce Peak 1214
I stayed with my 4 yr old grandson while my son and his wife moved to there New home in VT I felt safe, the valet was Fabulous always helpful . The restaurant was delicious for breakfast and easy and accommodating. My grandson loved the pool and the game room All in all we had a great time !

Luxurious Lake George Getaway
We had a fantastic stay! The location was perfect—just a short drive to Lake George Village and only 10 minutes from a wedding we attended in Queensbury. The house itself is absolutely beautiful; the photos don’t do it justice. It was even better in person—clean, spacious, and well-appointed. Would definitely stay here again!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

The Vista - 180º Mt. views w/Pool 12min to Stowe
Look no further if you're traveling with toddlers—this Airbnb is a dream for families! The location is perfect: tucked just outside of Stowe, it offers peaceful country vibes, a spacious backyard, and stunning mountain views from every window—all while being just a short drive from town. What really sets this home apart is how toddler-friendly it is. It's a BabyQuip heaven—stocked with everything from a high chair and nugget couch (iykyk!), to Fisher Price Little People toys, coloring supplies, a train set, games, and more. Our toddler had a blast and was perfectly content spending evenings at the house, thanks to the endless entertainment options. The host went above and beyond—the home was spotless, and the kitchen was fully equipped with all the essentials. Highly recommend for any family looking for a relaxing, kid-friendly escape in Vermont!

Charming Sugarbush Standalone Condo
Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

EPIC Stowe Getaway - Great For Families & Friends
weekend family trip for 6 of us and our dog(4 adults and 2 kids), plenty of space for everyone, and much larger than I expected! we enjoyed cooking in the well stocked kitchen, playing board games on the large dining room table, swimming in the pool and soaking in the hot tub, wrapping the nights up with a movie on their Roku TV! Kristin was very responsive in her communication, we had a lovely time and would love to plan future trips here again!
Weekly house rentals

3 story contemporary log cabin
The place was spotless and just as described. Check-in was super easy, and the host was incredibly responsive and flexible with our arrival time. Great experience overall—would definitely stay again!

Unique Serenity - 10 mins from Middlebury College
What a wonderful stay we had. The space is so clean and every amenity is thought of. Comfortable beds, great showers, and very close to Middlebury. Wish the weather had been better so we could have enjoyed the outdoor space more, but that will be for next time!

Renovated East Middlebury House
Nice accommodation for us to attend a graduation at middlebury college. Very quiet place and roomy place for 4 adults. We had a great stay for 2 nights.

cozy home for a relaxing summer getaway
Clover was the best host! Extra accomodating and very responsive. This house was sparkling clean and open and airy. The house was only 5 minutes from Snow Bowl, it was perfect! We will definitely stay here again!

Walk Everywhere and Enjoy a Historic Vermont Home
Jeffrey’s place was great. Quite walkable to all - close to campus and good restaurants. .Very cool place. I loved it. Had a small problem with the dryer and all was addressed asap. I would highly recommend! Great to be back in middlebury after all these years.

Bristol Falls Cozy Getaway
Warm, peaceful home in a beautiful little town. We stayed in winter with a big snow storm, house was Very comfortable, with delightfully chosen furnishings. Two nice coffee shops just down the street and wonderful restaurants in the area

Shimla - A Mountain Retreat
This was my second stay at this lovely home. It is very convenient to Routes 100 and 125. I love the babbling brook behind the house. It's always clean and has everything you need!

The Willow House: a Modern Vermont Retreat
This is a beautiful place to stay, surrounded by trees and next to a small stream with water sounds. We loved the space as well as the environs. Marcus and Amanda are great hosts, kind and responsive. Perfect.
Private house rentals

Vantage Point Guest House Mountain Views
This home was absolutely lovely and a perfect location for our trip to Fort Ticonderoga and Mount Independence! Jennifer was so responsive when we had any questions plus the maple syrup, farm fresh eggs and butter were such a warm gift! We would definitely like to stay in their home again, thank you!

Vermont Country Guest Cottage
We thoroughly enjoyed our stay. The view was terrific, ample space for three os, well stocked kitchen, gas grill on porch. Host was friendly and responsive. Clear instruction manual.

Rustic Charm
Lynn thought of everything. I have never been in a place that had so many comforts. Little water cups in the bathroom. Lots of washcloths and towels. Zip lock bags!!' We were there for less than 24 hours. If you are looking to stay in the area this is the place for you.

Quiet Contemporary Farmhouse
The posted photos are very revealing and accurate. Everything is spacious in this place, even though we were three couples. Interesting art and a wall of very good books! Kitchen functioned well and was well-stocked by AirBnB standards. Bucolic views from each of the grand windows.

Golden Hour on Lake Dunmore; Near Middlebury
This is my third time staying at Golden Hour. It is a lovely place on the lake. Morgan has furnished it nicely and the kitchen has all of the necessary items you will ever need for your stay. I love this place and I'll be back!

Comfortable, sunny artist home
Getting family together for the big graduation weekend at Middlebury College meant locating a nearby, comfy and pleasing space for family to stay. Zoe's place was outstanding. Beautiful. Unique. Convenient. It's a great place to stay when visiting your child at Middlebury, or just for a nice visit to this beautiful corner of Vermont.

Mountain view house
My sister and I stayed in Tatanka’s charming house during the weekend of my son’s graduation from Middlebury College, but it would have been a great place to stay just for a peaceful base to spend time in one of the most beautiful parts of Vermont. The property is completely private with a view of nothing but green lawn, green trees, and the Green Mountains. All its furnishings and appliances are solid, good quality, and work. The owner generously left us food in the freezer, milk in the fridge and ample supply of Green Mountain Coffee. A 5 in every aspect.

3-bedroom getaway 15 minutes from Middlebury
We spent my son's graduation weekend at Katie's place. We were so happy and pleased with everything! Thank you!!!
Quick stats about house rentals in Middlebury
Total rentals
30 properties
Nightly prices starting at
$117 NZD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
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- Sugarbush Resort
- Okemo Mountain Resort
- Smugglers' Notch Resort
- Gore Mountain
- Bolton Valley Resort
- Spruce Peak
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Autumn Mountain Winery
- Fort Ticonderoga
- Whiteface Mountain Ski Resort
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Fox Run Golf Club
- Killington Adventure Center
- Adirondack Extreme Adventure Course
- Lucky Bugger Vineyard & Winery
- Burlington Country Club
- Lincoln Peak Vineyard
- Montshire Museum of Science