Search Chalets in Middlebury

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 13 Chalets in Middlebury with updated reviews, rates, and availability.

Dreamy Artist Chalet in Secluded Historic Village

8.4 out of 10, Very Good, (5)
"My friend and I came to ride horses for two days at the Icelandic Horse Farm in Fayston, and we knew we wanted a comfortable place nearby for the night in between. The Chalet was in the perfect location between places to eat (we had pizza at the Blue Stone) and the stable. And it is LOVELY inside, beautifully furnished and stocked with everything you need, Highly recommend!"
The price is SAR 1,021
SAR 1,762 total
includes taxes & fees
3 Jan - 4 January 2025
Dreamy Artist Chalet in Secluded Historic Village

Magnificent any time of year

10.0 out of 10, Exceptional, (24)
"My wife and I came to Vermont for the first time and wanted to see the beautiful fall colors. 1st VRBO also. It was awesome. Very well appointed, clean, good communications, very accurate description. Couldnt have asked for more."
Magnificent any time of year

Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis

9.8 out of 10, Exceptional, (49)
"This is our third time staying at the property and love it! Great location and easy access to the valley. We had an issue with the microwave and Evelyn was quick to fix it for us! "
Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis

Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort

9.6 out of 10, Exceptional, (14)
"We had the pleasure to stay at this home for a weekend. The only complaint is we wish we could have stayed longer. The home is layed out perfectly and the views are stunning! Its such a great home to entertaine in. So much room and well thought out furnishings. The kitchen has EVERYTHING you could need.We noticed how great it would be for a family with children too!! So many books, toys and games.The check in process was smooth and we had excellent communication. We reccomend. this home highly...
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort

Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort

10.0 out of 10, Exceptional, (21)
"Great location and everything very well thought of and provisioned for stay. Owners very responsive."
Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort

Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

10.0 out of 10, Exceptional, (1)
"Truly a wonderful stay at the cabin. From the fully equipped kitchen (high end products), welcome basket full of goodies, big fluffy towels, phone chargers, comfortable furniture, Daisy paid attention to every detail! We’ll definitely be back and would recommend it to anyone. A little remote, but worth it."
The price is SAR 1,164
SAR 2,204 total
includes taxes & fees
6 Jan - 7 January 2025
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

Romantic Cozy Mountain Retreat near Killington

10.0 out of 10, Exceptional, (6)
"Our stay in this house was amazing, everything was perfect as described and like pictures. 20 mins from Killington Mountain and Pico Mountain."
Romantic Cozy Mountain Retreat near Killington

Modern Mad River Valley Chalet with Mountain Views Near Everything - 4BR/3BA

10.0 out of 10, Exceptional, (2)
"We wanted a cozy place to stay over Christmas, and we found it! The house is older, but so full of charm! Everything from check in to check out was a pleasant experience. The hosts were amazingly responsive, and the house included so many wonderful touches (including a S’mores basket and cookie cutters!) to make our family trip a fantastic experience! Early skiing at Sugarbush was less than a 25 minute drive, and was a very uncrowded and beautiful place for our two teens to learn to ski for the...
Modern Mad River Valley Chalet with Mountain Views Near Everything - 4BR/3BA

Waterfront Chalet with views of lake & mountains. Stay Christmas & New Years

10.0 out of 10, Exceptional, (1)
"The house was very nice. Warmly furnished. Very comfortable. We felt at home. Much time spent absorbing the lake view from the deck. We took full advantage of the lake for swimming and kayaking. Overall a great trip. One suggestion: The listing should mention linens not provided."
Waterfront Chalet with views of lake & mountains. Stay Christmas & New Years

Chalet Vermont, ski in out at Sugarbush

2.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was beautiful. Thank you Jack for all you did to make our stay everything we had hoped for. Would love to come back!"
The price is SAR 2,065
SAR 3,844 total
includes taxes & fees
6 Jan - 7 January 2025
Chalet Vermont, ski in out at Sugarbush

Warren VT Chalet for Ski, Summer + Fall Fun, WIFI

Warren VT Chalet for Ski, Summer + Fall Fun, WIFI

Mad Meadows 5 Bedroom Chalet by RedAwning

3.0 star property
Mad Meadows 5 Bedroom Chalet by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlebury

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (134)
"Cabin had everything we needed and more. We found it to be a great location for the small day trips we did to surrounding towns. Location is just gorgeous. "
The price is SAR 901
SAR 1,754 total
includes taxes & fees
23 Jan - 24 January 2025
Stetson Hollow Cabin by Stetson Brook

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (178)
"We had a lovely time, and Dan was very accommodating, especially when we had to delay our trip by a day due to a snow storm!"
The price is SAR 526
SAR 673 total
includes taxes & fees
6 Jan - 7 January 2025
Ultimate relaxing vacation
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.