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Compare 34 Chalets in Middlesex with updated reviews, rates, and availability.

Large Cozy 2-bedroom condo with WiFi, AC on the Stowe/Morristown town line

9.6 out of 10, Exceptional, (7)
"Great house, great area"
The price is AED 863
AED 1,687 total
includes taxes & fees
11 Jan - 12 January 2025
Large Cozy 2-bedroom condo with WiFi, AC on the Stowe/Morristown town line

Vintage Chalet Chalet w/fireplace, 2 mins from SKI hill

10.0 out of 10, Exceptional, (64)
"Quaint chalet "
Vintage Chalet Chalet w/fireplace, 2 mins from SKI hill

Blue Jay's Blue Chalet - 2 mins from SKI hill

10.0 out of 10, Exceptional, (30)
"We had a good time."
Blue Jay's Blue Chalet - 2 mins from SKI hill

Owls Head Estate - Unmatched & Unforgettable Views

10.0 out of 10, Exceptional, (5)
"This was a beautiful house and perfect for family. The location and views cannot be beat. The photos in the listing don’t do the house justice. The house also has a beautiful backyard with views of the mountains and gorgeous landscaping. Our only concern was that there is no air conditioning in the house so recommend you stay here in cooler months."
Owls Head Estate - Unmatched & Unforgettable Views

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

The price is AED 1,473
AED 3,266 total
includes taxes & fees
23 Dec - 24 Dec
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI

Maple ridge chalet

10.0 out of 10, Exceptional, (7)
"This was as enjoyable as any property we have ever rented in almost 50 years. We have stayed in several other rentals in this same area over the last decade but none of them are as enjoyable as this one."
Maple ridge chalet

Copper Roof Chalet - 3 mins from SKI hill.

10.0 out of 10, Exceptional, (13)
"This chalet was an excellent basecamp for my husband and I as well as my in-laws for a long weekend during leaf season. Smugglers Notch resort was less than five mins away, and the town of Cambridge was less than 10 for groceries or more dining options. 20 mins or less to hiking trails in the notch or Stowe resort. "
Copper Roof Chalet - 3 mins from SKI hill.

Stoweic Views - Luxury Dream Vacation Home

10.0 out of 10, Exceptional, (1)
"There were 14 of us - 4 families. The space was perfect for our needs. The bathrooms and kitchen were well appointed with all our needs met. The family enjoyed the hot tub, the pool table and everything about the house was wonderful. Thank you for making our 45th wedding anniversary family vacation so memorable."
Stoweic Views - Luxury Dream Vacation Home

Classic Stowe Ski Chalet by RedAwning

10.0 out of 10, Exceptional, (42)
"Last September I took a sisters trip to Vermont and liked this place so much I booked it for me my husband and two adult children. The chalet is clean and comfortable and plenty of room for our family of four. Great time does not disappoint. "
Classic Stowe Ski Chalet by RedAwning

A cozy family retreat perfectly located between Stowe Village & Trapp’s Lodge

10.0 out of 10, Exceptional, (7)
"Wonderful vacation getaway to see the spectacular fall leaves."
A cozy family retreat perfectly located between Stowe Village & Trapp’s Lodge

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

Modern Mountain Home at Wildewood

Modern Mountain Home at Wildewood

Stowe Trapp Four Season Paradise - One Bedroom Villa Suite

9.6 out of 10, Exceptional, (24)
"If you are looking for a quiet get away- this property is for you. Relaxing views of the mountains. Local hiking and biking on premises. Villas were located far enough away to give space and privacy. You are close to Von Trapp restaurants and amenities but you need to drive into Stowe for other entertainment/restaurants/pubs. "
Stowe Trapp Four Season Paradise - One Bedroom Villa Suite

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 AED 999
AED 1,728 total
includes taxes & fees
20 Dec - 21 Dec
Dreamy Artist Chalet in Secluded Historic Village

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

Classic Stowe Ski 3 Bedroom Chalet by RedAwning

4.0 star property
10.0 out of 10, Exceptional, (1)
Classic Stowe Ski 3 Bedroom Chalet by RedAwning

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

Large Ski Chalet minutes from Smuggler's Notch!

10.0 out of 10, Exceptional, (3)
"The cabin was more spacious than anticipated. Everything was very clean and well-appointed. Five minute drive to Smuggler's Notch resort. We look forward to staying again."
Large Ski Chalet minutes from Smuggler's Notch!

Modern Chalet Retreat | Close Stowe Mt. Resort & Village

10.0 out of 10, Exceptional, (17)
"Myself and 8 of my closest friends and family stayed at Kyle and Alexa’s beautiful Stowe chalet! It was a beautiful home. It had everything we needed and more! It is truly the ideal getaway house. The location was perfect! We were never traveling more than 10 minutes to get to town, a brewery, a mountain resort, etc. the only thing we’d recommend, being in a house full of girls, is a full body mirror somewhere! We all hope to make it back to Stowe some day and would LOVE to stay in their home...
Modern Chalet Retreat | Close Stowe Mt. Resort & Village
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 Middlesex

Stowe Cabins in the Woods

2.5 star property
8.8 out of 10, Excellent, (275)
"Not bad. Needs an update but for the price it was adorable. "
Stowe Cabins in the Woods

Smugglers' Notch Resort

3.0 star property
8.0 out of 10, Very Good, (106)
"I didn’t like that we did not have shampoo or conditioner in our unit! I also thought each unit should carry salt and pepper! The facility was not full and we had a person next to us! I would think you would separate your guests out for more privacy and quietness! "
Smugglers' Notch Resort

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 AED 882
AED 1,715 total
includes taxes & fees
6 Jan - 7 January 2025
Stetson Hollow Cabin by Stetson Brook
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.