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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

Magnificent any time of year
Outdoor dining

Magnificent any time of year

10.0 out of 10, Exceptional, (28)
"Wonderful host and great property."
The price is SAR 656
SAR 1,395 total
includes taxes & fees
18 May - 19 May
Magnificent any time of year
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Dining

Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont

10.0 out of 10, Exceptional, (5)
"Relaxing stay in a great area."
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Exterior

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

9.6 out of 10, Exceptional, (14)
"Great place with lots of charm & room for all!"
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Dreamy Artist Chalet in Secluded Historic Village
Fridge, microwave, oven, stovetop

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 1,020
SAR 1,765 total
includes taxes & fees
30 Apr - 1 May
Dreamy Artist Chalet in Secluded Historic Village
Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis
Exterior

Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis

9.8 out of 10, Exceptional, (50)
"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
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Interior

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

10.0 out of 10, Exceptional, (2)
"The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended."
The price is SAR 1,125
SAR 2,159 total
includes taxes & fees
30 Apr - 1 May
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Interior

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

10.0 out of 10, Exceptional, (4)
"excellent house- very close to sugarbush "
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort
Outdoor dining

Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort

10.0 out of 10, Exceptional, (22)
"Great location and everything very well thought of and provisioned for stay. Owners very responsive."
Bayou Chalet – Your Perfect Getaway Near Sugarbush Resort
Modern Mad River Valley Chalet with Mountain Views Near Everything - 4BR/3BA
Property grounds

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
Romantic Cozy Mountain Retreat near Killington
Exterior

Romantic Cozy Mountain Retreat near Killington

10.0 out of 10, Exceptional, (6)
"Thank you for offering a fabulous place for a family ski meet up. The place was just as described!"
Romantic Cozy Mountain Retreat near Killington
Cozy 4-bedroom chalet with WiFi, AC, fireplace in adventurous Mad River Valley
Exterior

Cozy 4-bedroom chalet with WiFi, AC, fireplace in adventurous Mad River Valley

Cozy 4-bedroom chalet with WiFi, AC, fireplace in adventurous Mad River Valley
Mad Meadows 5 Bedroom Chalet by RedAwning
Chalet, 5 Bedrooms | Exterior

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.
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Other property types in Middlebury

Beautiful brand new 1-bedroom apt with gorgeous views
Exterior

Beautiful brand new 1-bedroom apt with gorgeous views

10.0 out of 10, Exceptional, (43)
"We enjoyed our visit very much!"
Beautiful brand new 1-bedroom apt with gorgeous views
Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (10)
"Absolutely wonderful place and super friendly staff "
The price is SAR 542
SAR 696 total
includes taxes & fees
30 Apr - 1 May
Trout House Village Resort
Bridges Resort
Condo, 2 Bedrooms (Standard) | Private kitchen

Bridges Resort

3.5 star property
7.6 out of 10, Good, (10)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
Bridges Resort
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.