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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 12 Chalets in Middlebury with updated reviews, rates, and availability.

Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Front of the chalet that overlooks the lake

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

10.0 out of 10, Exceptional, (3)
"Very clean, great access to the water. Plenty of nice cooking gear, very happy with the experience, very clean and comfortable!"
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Magnificent any time of year
Exterior detail

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."
The price is SAR 938
SAR 1,752 total
includes taxes & fees
11 Feb - 12 Feb
Magnificent any time of year
Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis
Great Chalet; well maintained; excellent condition; great views!

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
Dreamy Artist Chalet in Secluded Historic Village
Open Kitchen area

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 848
SAR 1,559 total
includes taxes & fees
29 Jan - 30 Jan
Dreamy Artist Chalet in Secluded Historic Village
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Stunning Views of Sugarbush

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
2 level chalet with deck overlooking golf course with views of the valley

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.
Living area

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 1,088
SAR 2,101 total
includes taxes & fees
28 Jan - 29 Jan
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Romantic Cozy Mountain Retreat near Killington
Bathroom

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
Living area

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

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

10.0 out of 10, Exceptional, (2)
"We enjoyed this house nestled among the trees yet just off the main road to Warren and perfectly located between Sugarbush and MRG. We were able to create family dinners and although spartan in the way of furniture, still cozy and comfortable. Master bedroom is very nice, main floor bedroom also. Beds comfortable. Downstairs bedrooms are colder than the rest of the house."
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Mad Meadows 5 Bedroom Chalet by RedAwning
Golf

Mad Meadows 5 Bedroom Chalet by RedAwning

3.0 star property
Mad Meadows 5 Bedroom Chalet by RedAwning
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
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

Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (478)
"It was a delight to be back! The cabin was as cozy and perfect as we remembered, with everything we needed for a long weekend. The kids enjoyed sledding, building a fire, the hot tub, and a Harry Potter dual feature on the projector, among many other activities. We will be back soon!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Pristene lakefront property - charming, quiet, and rustic for nature lovers.
Breathtaking sunsets on Cedar Lake

Pristene lakefront property - charming, quiet, and rustic for nature lovers.

8.0 out of 10, Very Good, (71)
"Plenty of room for the whole family."
Pristene lakefront property - charming, quiet, and rustic for nature lovers.
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.