House holiday rentals in Middlebury

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Popular amenities for house rentals in Middlebury

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars1 week ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
Top guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month ago
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!
Top guest favourite
Home in Killington
4.99 out of 5 average rating, 135 reviews

SugarBear- Pool, AC, Sauna, Gym, Tennis!

JennRating, 5 stars1 month ago
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.
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 stars3 weeks 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.
Top guest favourite
Home in Morristown
5 out of 5 average rating, 7 reviews

The Vista - 180º Mt. views w/Pool 12min to Stowe

GaryRating, 5 stars1 week ago
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!
Superhost
Home in Sugarbush Village
4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

PerryRating, 5 stars3 months ago
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!
Top guest favourite
Home in Crown Point
5 out of 5 average rating, 20 reviews

Stunning Mountain Top Cabin

Jan MichaelRating, 5 stars4 days ago
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!
Top guest favourite
Home in Stowe
4.98 out of 5 average rating, 267 reviews

EPIC Stowe Getaway - Great For Families & Friends

KatieRating, 5 stars2 weeks ago
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

Top guest favourite
Home in New Haven
4.97 out of 5 average rating, 38 reviews

Unique Serenity - 10 mins from Middlebury College

DaltonRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Vergennes
4.9 out of 5 average rating, 41 reviews

Vermont Country Guest Cottage

DanielRating, 5 stars1 day ago
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.
Guest favourite
Home in Cornwall
4.96 out of 5 average rating, 48 reviews

Quiet Contemporary Farmhouse

AlanRating, 5 stars1 month ago
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.
Top guest favourite
Home in New Haven
5 out of 5 average rating, 12 reviews

Comfortable, sunny artist home

EdRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Bristol
4.95 out of 5 average rating, 86 reviews

Bristol Falls Cozy Getaway

PatrickRating, 5 stars4 months ago
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
Top guest favourite
Home in Middlebury
5 out of 5 average rating, 93 reviews

The Little House

JodiRating, 5 stars1 month ago
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.
Top guest favourite
Home in Cornwall
4.97 out of 5 average rating, 35 reviews

Mountain view living near Middlebury, Vermont

MattRating, 5 stars3 months ago
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!
Guest favourite
Home in Middlebury
4.98 out of 5 average rating, 49 reviews

Downtown Middlebury Farmhouse

MelissaRating, 5 stars1 month ago
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

Top guest favourite
Home in Shoreham
5 out of 5 average rating, 75 reviews

Vantage Point Guest House Mountain Views

JacobRating, 5 stars7 months ago
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!
Guest favourite
Home in Ripton
4.97 out of 5 average rating, 91 reviews

cozy home for a relaxing summer getaway

CourteneyRating, 5 stars3 months ago
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!
Top guest favourite
Home in Crown Point
5 out of 5 average rating, 35 reviews

Rustic Charm

RobertaRating, 5 stars5 days ago
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.
Top guest favourite
Home in Salisbury
4.98 out of 5 average rating, 54 reviews

Golden Hour on Lake Dunmore; Near Middlebury

KimRating, 5 stars1 week ago
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!
Superhost
Home in Weybridge
5 out of 5 average rating, 3 reviews

3BR Vermont Family Retreat 5 mins from Middlebury

JoeyRating, 5 stars3 weeks ago
Such a beautiful space. Warm, cozy, Vermont kind of feeling. Thanks for sharing your home!
Superhost
Home in Ripton
4.72 out of 5 average rating, 18 reviews

Cozy & Updated Year-Round Farmhouse -Kid Approved!

RachelRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Lincoln
4.96 out of 5 average rating, 45 reviews

Mountain view house

ThomasRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Hancock
4.97 out of 5 average rating, 62 reviews

Shimla - A Mountain Retreat

CaraRating, 5 stars2 weeks ago
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

Destinations to explore

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  4. Addison County
  5. Middlebury
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