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Compare 11 Chalets in Middlebury with updated reviews, rates, and availability.

Summer is here! Hiking, biking, river-swims... So much to do!!
10.0 out of 10, Exceptional, (20)
"We didn’t want to leave it was so nice! Josh was a wonderful host too. He told us all the good places to go and communication was great. The home was perfect. Beautiful, warm and cozy. Had everything we needed for our stay and the kitchen was great. The location is lovely. Remote but easy to get to and close to the town and other towns. Lots of great hiking and views everywhere! We hope to visit again soon. "
The price is SAR 747
SAR 1,526 total
includes taxes & fees
24 Sep - 25 Sep
Summer is here! Hiking, biking, river-swims... So much to do!!
Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis
9.8 out of 10, Exceptional, (48)
"Highly recommend"
Comfortable, Charming Mountain Chalet. Ski, Golf, Tennis
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 1,778 total
includes taxes & fees
9 Oct - 10 Oct
Dreamy Artist Chalet in Secluded Historic Village
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
9.6 out of 10, Exceptional, (13)
"We came to the Mad River Valley for our son’s wedding at The Round Barn. Our extended family all stayed together- 4 generations plus two dogs. We had a fabulous stay (and wedding). Highlights were the large house with lots of places for people to hang out, lots of bedrooms and bathrooms, great deck with a lovely view of Sugarbush, hot tub (although we never managed to find the time to use it), very functional kitchen with any pan or utensil you might need, very convenient parking (we had 6...
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Amazing Location! 4BR, 2BA chalet 5 min from Sugarbush. On golf course!
10.0 out of 10, Exceptional, (21)
"Great location and everything very well thought of and provisioned for stay. Owners very responsive."
Amazing Location! 4BR, 2BA chalet 5 min from Sugarbush. On golf course!
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."
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 w/ expansive views of lake & mountains. Available for Foliage!
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 w/ expansive views of lake & mountains. Available for Foliage!
Enchanting Vermont chalet, ski in out at Sugarbush
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time at this property. It was a wonderful location. We felt like we were in a luxurious treehouse with a view. All the sliding glass doors really helped with cooling off in the heat of the day. Comfy beds and everything we needed. Would definitely recommend."
Enchanting Vermont chalet, ski in out at Sugarbush
Mad Meadows 5 Bedroom Chalet by RedAwning
3.0 star property
Mad Meadows 5 Bedroom Chalet by RedAwning
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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

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (462)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"We had a wonderful time .. accommodations could not have been more romantic 💝 "
Cozy Loft for two with Hot Tub
Ultimate relaxing vacation
9.8 out of 10, Exceptional, (168)
"Very nice property set back away from noisy traffic. The pond view was beautiful, cabin was well furnished, beds and living room were comfortable. Private dock was a plus and the water depth was gradual, making it ideal for swimming. Host Dan was very responsive to questions. My wife and I had a great couple of nights at the cabin and we’ll definitely return in the Spring!"
The price is SAR 600
SAR 769 total
includes taxes & fees
10 Oct - 11 Oct
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.