Search Chalets in Middletown Springs from CA $480

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middletown Springs Chalets

Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (35)
"Really enjoyed this home. Was a weekend getaway with friends and there was lots of room for us. Especially enjoyed the sauna. Kitchen is well stocked. All was great. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Outdoor spa tub

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (35)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Exterior

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (51)
"All around great stay. Had some slight heat issues day 1 that were fixed imemdiately!"
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Outdoor dining

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

2.0 star property
8.0 out of 10, Very good, (1)
"It was easy to check in and out and there was plenty of parking. There were also ACs in all of the bedrooms but 1. This was important since it was 90 degrees. We only wish the ice machine that was provided worked. The living room furniture, especially the couch, was amazingly comfy. We did a lot of bonding in that space. When we walked in on the first evening, there were some windows open, and there was a furry chicken nugget sitting on the arm of a chair though. The basement had bedrooms in...
The price is CA $646
CA $1,609 total
includes taxes & fees
Aug 10 - Aug 11
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Cozy chalet minutes from Okemo Mtn & VAST
Interior

Cozy chalet minutes from Okemo Mtn & VAST

2.0 star property
Cozy chalet minutes from Okemo Mtn & VAST
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Interior

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
The price is CA $1,375
CA $2,749 total
includes taxes & fees
Aug 10 - Aug 11
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour
Exterior

Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour

9.8 out of 10, Exceptional, (104)
"My family was so fortunate to find this wonderful home away from home. We lacked for nothing. The three floors allowed us privacy when needed and the middle floor accommodated our large family comfortably and cozily. The kitchen had all the supplies for all of us to be comfortably seated AND the kitchen table was big enough to seat 9 of us with room to spare. The location was peaceful. There are many activities to participate in in the area. We especially liked Merck forest but would have been...
Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Property grounds

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

9.8 out of 10, Exceptional, (125)
"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Killington Chalet - Great Space and Location!
Exterior

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Our group of 10 friends had a wonderful stay at the Chalet. Great location to the mountain and local restaurants and entertainment. Plenty of room to spread out and great communal area as well. "
Killington Chalet - Great Space and Location!
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Fridge, microwave, oven, stovetop

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"The house was equipped with everything we needed! Cant wait to come back! "
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
South View Chalet!
Fridge, microwave, oven, stovetop

South View Chalet!

9.2 out of 10, Wonderful, (26)
"Great location and house. Perfect for large groups, there is plenty of space with multiple rooms so your group can spread out. Minutes to Killington mountain. "
South View Chalet!
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Fridge, microwave, oven, stovetop

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

9.6 out of 10, Exceptional, (33)
"We had a fabulous stay here. Owner was v communicative and accommodating."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Classic Alpine Vermont Chalet
Property grounds

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"Easiest vrbo experience we’ve had to date."
Classic Alpine Vermont Chalet
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Pool

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
The price is CA $480
CA $1,317 total
includes taxes & fees
Sep 2 - Sep 3
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Outdoor spa tub

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

10.0 out of 10, Exceptional, (1)
"Awesome property and very responsive staff! Highly recommended. "
The price is CA $938
CA $2,130 total
includes taxes & fees
Aug 10 - Aug 11
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Fridge, microwave, stovetop, dishwasher

Mountain View Chalet Fabulous views large entertaining area just off Killington Road

10.0 out of 10, Exceptional, (1)
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
Interior

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

9.8 out of 10, Exceptional, (59)
"We stayed along with 2 other families while in time visiting Okemo mountain. The house was very welcoming, clean and exactly how the picture showed it. We would stay here again next time we were in time. "
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
The Whimsical Chalet 3 Bedroom Chalet by RedAwning
Chalet, 3 Bedrooms | Dining

The Whimsical Chalet 3 Bedroom Chalet by RedAwning

3.0 star property
The Whimsical Chalet 3 Bedroom Chalet by RedAwning
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

9.8 out of 10, Exceptional, (22)
"Victoria and Erica were wonderful hosts, everything was as expected and they were very responsive. Graciously arranged for extra snow plowing due to some pretty significant snowfall. Had room for three couples and kids, 10 in all, very comfortably. Would stay again!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.
Dining

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

9.0 out of 10, Wonderful, (2)
"Stayed for a ski weekend and it was a nice quiet house on a quiet street but still situated close to the resorts."
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Springs Hotel Reviews

Cortina Inn

Cortina Inn

8/10 Good
"So much potential. The parking lot is unkempt, many facilities are shut down, there only seems to be a single staff member on site. The carpets are beaten down, the whole hotel smelled of cleaning agents, and our room smelled of cigarettes. Putting that aside, rooms were actually clean. No bugs, dirt or anything. It was eerily empty and quiet, but some might like that. The staff member was super friendly and helpful. I feel if this place put any money into recovering the parking lot and physical appearance overall that itd be a 5 star experience."
Christian 2-night trip
Posted 1 day ago
Cortina Inn