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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 53 Chalets in Rutland with updated reviews, rates, and availability.

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)
"Fun family get away!"
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
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)
"We had 4 families with a range of kids from 16-5. The house was the perfect space to spread out to give everyone space and things to do! The house was clean and stocked with whatever you needed during the stay. We’ve done a lot of VRBO rentals and this was one of our best experiences! Plus, the trail was amazing to have in the backyard! "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Dining

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

10.0 out of 10, Exceptional, (6)
"Relaxing stay in a great area."
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
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,
BearHaus- Central AC, HUGE Hot Tub, FirePit
Pool

BearHaus- Central AC, HUGE Hot Tub, FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
The price is AED 1,000
AED 3,118 total
includes taxes & fees
15 May - 16 May
BearHaus- Central AC, HUGE Hot Tub, FirePit
"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, (34)
"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
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Smart TV, DVD player, books, stereo

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

9.8 out of 10, Exceptional, (44)
"Have always wanted to stay in a chalet and now we have. Had a very nice time in a unit that was well equipped. Thank you Janie. "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Private kitchen

Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

9.6 out of 10, Exceptional, (5)
"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
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
The price is AED 1,725
AED 4,297 total
includes taxes & fees
14 May - 15 May
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Property grounds

Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun

2.0 star property
10.0 out of 10, Exceptional, (11)
"The place was nice, the hosts were really excellent and responsive- and the location is very nice. It’s not too far to go hiking, swimming or kayaking!!!"
The price is AED 731
AED 1,761 total
includes taxes & fees
7 Jun - 8 Jun
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
South View Chalet!
Fridge, microwave, oven, stovetop

South View Chalet!

9.2 out of 10, Wonderful, (26)
"The house was perfect for our group. The outdoor space was great and the view is beautiful. Would certainly stay here again!"
South View Chalet!
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)
"Had a great time here this week, quick access to Okemo, hope to stay again next season."
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Interior

Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

10.0 out of 10, Exceptional, (1)
The price is AED 1,034
AED 2,962 total
includes taxes & fees
14 May - 15 May
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Aerial view

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

10.0 out of 10, Exceptional, (10)
"Great house, made our ski weekend easy and fun. House is better than the pictures."
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
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
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 AED 2,505
AED 5,670 total
includes taxes & fees
14 May - 15 May
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

10.0 out of 10, Exceptional, (68)
"House is beautiful, well stocked. Kat was exceptional as host; all my questions were promptly answered. Location is ideal"
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Okemo 6 Bedroom Chalet.
Smart TV, fireplace, video games, stereo

Okemo 6 Bedroom Chalet.

9.4 out of 10, Exceptional, (23)
"We enjoyed our stay at this cozy chalet! The 5 bedrooms and 2 living spaces allow for plenty of room for everyone. The location is convenient for skiing at okemo and close to everything in town. Communication with the owner was very good, especially when we had an issue with the hot tub. I highly recommend this home and am already looking forward to coming back! For large groups I might recommend bringing extra towels and for some reason the kitchen was short on bowls."
Okemo 6 Bedroom Chalet.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

10.0 out of 10, Exceptional, (39)
"This was the second time we have stayed at this property and it did not disappoint. Plenty of room for everyone. Clean and well furnished. Highly recommend it."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Property grounds

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

8.8 out of 10, Excellent, (5)
"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
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 Rutland

Stunning Wedding & Retreat Venue (19 bedrooms)
Dining

Stunning Wedding & Retreat Venue (19 bedrooms)

10.0 out of 10, Exceptional, (2)
"We hosted an intimate company retreat at the beautiful, idyllic Red Clover and we could not have had a better experience. Everything was seamless, from the planning stage with Carol and her team, check-in, throughout the weekend, and checking out. The property was perfectly kept and equipped-- we had everything we needed and more-- and this has set the bar VERY high for future events. Thanks so much Red Clover Team!!!"
Stunning Wedding & Retreat Venue (19 bedrooms)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ultimate relaxing vacation

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (189)
"It was our 4th time to staying in the cabin and we will be back again, definitely "
The price is AED 551
AED 708 total
includes taxes & fees
19 May - 20 May
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.