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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Compare 35 Chalets in Middlesex with updated reviews, rates, and availability.

Classic Stowe Ski Chalet by RedAwning
"Building","House","Cabin","Cottage","Log Cabin"

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
Blue Jay's Blue Chalet - 2 mins from SKI hill
Covered with snow

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
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 AED 918
AED 1,715 total
includes taxes & fees
11 Feb - 12 Feb
Magnificent any time of year
Owls Head Estate - Unmatched & Unforgettable Views
Enjoy Amazing Views from our Owl`s Head Luxury Post and Beam Home

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
Large Cozy -2 floor, 2-bedroom condo with WiFi, Game Room, 5 Minutes to Stowe
Room

Large Cozy -2 floor, 2-bedroom condo with WiFi, Game Room, 5 Minutes to Stowe

9.4 out of 10, Exceptional, (8)
"Great house, great area"
The price is AED 731
AED 1,526 total
includes taxes & fees
20 Jan - 21 Jan
Large Cozy -2 floor, 2-bedroom condo with WiFi, Game Room, 5 Minutes to Stowe
Maple ridge chalet
Exterior

Maple ridge chalet

10.0 out of 10, Exceptional, (7)
"We stayed here for a family wedding that was about 20 min away. The house was very clean and easy to get to. The porch was our favorite place to sit at with the nice views and being secluded from everyone. Would definitely come back and stay here again."
Maple ridge chalet
Copper Roof Chalet - 3 mins from SKI hill.
Exterior -Winter

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
Relax in the Living room with amazing Mountain Views

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
A cozy family retreat perfectly located between Stowe Village & Trapp’s Lodge
A perfect family get-away! A well provisioned house w an expansive outdoor deck

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
Vintage Chalet Chalet w/fireplace, 2 mins from SKI hill
Vintage Chalet - Front winter

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
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
Modern Mountain Home at Wildewood
Fabulous floor to ceiling windows grace the living room

Modern Mountain Home at Wildewood

Modern Mountain Home at Wildewood
World-Class Villa @ Stowe & Trapp
Snowing at the Villa

World-Class Villa @ Stowe & Trapp

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. "
World-Class Villa @ Stowe & Trapp
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 AED 999
AED 1,711 total
includes taxes & fees
20 Jan - 21 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
Classic Stowe Ski 3 Bedroom Chalet by RedAwning
Exterior

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
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
Large Ski Chalet minutes from Smuggler's Notch!
Exterior

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
Exterior

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
Relaxing Retreat: 7 mins to both Mountain and Village: Ski, Bike, Hike & Unwind
Entrance to chalet in summer - surround by nature.

Relaxing Retreat: 7 mins to both Mountain and Village: Ski, Bike, Hike & Unwind

10.0 out of 10, Exceptional, (29)
"Great long weekend in Stowe! Great location between the eats/drinks and the mountain activities. Look forward to returning during the ski season!!"
Relaxing Retreat: 7 mins to both Mountain and Village: Ski, Bike, Hike & Unwind
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
Exterior

Stowe Cabins in the Woods

2.5 star property
8.8 out of 10, Excellent, (278)
"Great owners, easy to use, close to everything. Awesome price for 6 people and a dog. Thank you"
Stowe Cabins in the Woods
#319 | Studio | Sunny Spruce | 3rd Floor Village & Mountain Views

#319 | Studio | Sunny Spruce | 3rd Floor Village & Mountain Views

10.0 out of 10, Exceptional, (84)
"We had a great time in our family holiday ski trip! The location was amazing, convenient for everything."
#319 | Studio | Sunny Spruce | 3rd Floor Village & Mountain Views
Clean & Bright Condo near Slopes & Lakes with Amazing Walkable Locale

Clean & Bright Condo near Slopes & Lakes with Amazing Walkable Locale

8.4 out of 10, Very Good, (53)
"There are a lot of good things about our stay. We loved being able to walk through Stowe at all hours. We loved the convenience of having a market right next door. And I was able to get a haircut right downstairs. The rec path was close and delightful to walk on. But we had no hot water--none--for the entire stay. Before arriving we were told the hot water heater needed a part that wouldn't be available for 3 days. We were even offered another rental to use instead, but it wasn't right downtown...
Clean & Bright Condo near Slopes & Lakes with Amazing Walkable Locale
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.