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

Luxury Condo Tucked in the Heart of Killington
Very nice place easy access to routes 4 and 100 with plenty of things to do

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.

Luxury Alpine Studio. Ski In Ski Out. Spruce Peak
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.

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!

Stunning Mountain Top Cabin
My wife, our dog, and I had a wonderful stay at Shyra's place. The home was clean, warm, and welcoming—our dog felt right at home. Waking up to stunning views of the high peaks from the backyard was truly unforgettable. Short drives to Schroon Lake and Ticonderoga. A great home base of you're looking to hike any of the Adirondack high peaks. Shyra was communicative and very responsive throughout our stay. We’re already looking forward to our next visit! Thank you for having us!

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

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!

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.

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.

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.

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

The Little House
I wish had more opportunities to return to Middlebury because Andrea & Jeremy’s beautiful home is the first place I’d choose to book. The house is light-filled, cozy and comfortable but also tastefully minimalist with healthy thriving plants softening each corner. Andrea is a thoughtful host leaving notes, making recommendations and just generally being a lovely person during the communication process; we felt right at home. Beds are comfy and the house is immaculate. We loved walking into town and to the campus for our events. I highly recommend this home for your next stay in Middlebury.

Mountain view living near Middlebury, Vermont
We spent a lovely four days at Angela's home. We were two couples staying in the area to attend a college sporting event and Angela's home proved to be a perfect place to stay. The home is located a few miles from Middlebury College in a charming and picturesque area. The photos do not do it justice. The views from the windows, which overlook the VT mountains, are nothing less than stunning. The home is spotless and meticulously maintained. Angela has wonderful taste in art and the home is beautifully decorated. The large, newly renovated kitchen was well stocked with high end appliances, dishes and glasses. The linens and towels in the bedrooms and bathrooms were of excellent quality. The beds were very comfortable. There were thoughtful touches left by Angela such as fresh flowers in three of the rooms, as well as wine, cheese and coffee for us to enjoy. All in all, it was an outstanding stay, and I highly recommend this Airbnb to other travelers!

Downtown Middlebury Farmhouse
The house is in a great location and is very cute and clean. The downstairs has plenty of room for six to entertain and relax.
Private house rentals

Vantage Point Guest House Mountain Views
A fantastic location for a family vacation! The house was very spacious and comfortable and there was a ton to do (indoors & outdoors) in the area. We thoroughly enjoyed our stay and would love to come back!

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!

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.

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!

3BR Vermont Family Retreat 5 mins from Middlebury
Such a beautiful space. Warm, cozy, Vermont kind of feeling. Thanks for sharing your home!

Cozy & Updated Year-Round Farmhouse -Kid Approved!
Once again, we had a wonderful stay at Kate's home! It is comfortable, clean, and well equipped. The keys are easy to access. There is not much cell service around the area, so be sure to read the instructions about getting on WiFi before you get to the house. We had no trouble accessing the WiFi, so it was not a problem for us. The surroundings are beautiful, and it is an easy drive to Middlebury College, where we were celebrating our daughter's graduation. It was wonderful to have such a comfortable home for our extended family to gather for this important occasion. Highly recommend!

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.

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!
Quick stats about house rentals in Middlebury
Total rentals
30 properties
Nightly prices starting at
₹6,058 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
Wifi availability
30 properties include access to wifi
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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
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Fox Run Golf Club
- Vermont National Country Club
- Adirondack Extreme Adventure Course
- Montshire Museum of Science
- Lincoln Peak Vineyard
- Killington Adventure Center
- Burlington Country Club
- Lucky Bugger Vineyard & Winery