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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Rutland vacation homes

Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 364
AED 889 total
includes taxes & fees
25 May - 26 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AED 701
AED 1,604 total
includes taxes & fees
27 May - 28 May
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 979
AED 2,170 total
includes taxes & fees
25 May - 26 May
large ski ranch hot tub close to killington pets ok
Microwave, oven, stovetop, dishwasher

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AED 1,377
AED 2,703 total
includes taxes & fees
25 May - 26 May
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is AED 476
AED 558 total
includes taxes & fees
7 Jun - 8 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 496
AED 1,220 total
includes taxes & fees
25 May - 26 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AED 496
AED 1,220 total
includes taxes & fees
25 May - 26 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"We had a wondetful time! Thank you! The hosts were so accommodating and the place is the perfect winter wonderland getaway. "
United States
Gabriele K.
The price is AED 496
AED 1,748 total
includes taxes & fees
25 May - 26 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AED 571
AED 2,681 total
includes taxes & fees
25 May - 26 May
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
TV, DVD player, offices

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is AED 1,073
AED 2,489 total
includes taxes & fees
28 May - 29 May
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
25 May - 26 May
CozyDen - AC, Grill, Bike to Mountain, Porch!
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 661
AED 2,403 total
includes taxes & fees
27 May - 28 May
The Tower House | Hot Tub | Firepit | Dog-Friendly
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is AED 698
AED 2,053 total
includes taxes & fees
26 May - 27 May
Large Killington Area Home | Sleeps 7 | Game Room
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AED 724
AED 2,820 total
includes taxes & fees
25 May - 26 May
Breakaway House by Killington Vacation Rentals
Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 391
AED 2,019 total
includes taxes & fees
25 May - 26 May
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 391
AED 2,019 total
includes taxes & fees
25 May - 26 May
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is AED 985
AED 2,197 total
includes taxes & fees
26 May - 27 May
New Ludlow Village Home with Stunning Okemo Mountain View
TV, fireplace, foosball, stereo

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is AED 845
AED 1,717 total
includes taxes & fees
25 May - 26 May
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
The price is AED 735
AED 1,378 total
includes taxes & fees
25 May - 26 May
Cozy Moonship Yurt in the woods
Indoor pool, a heated pool

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Location/proximity to Killington is awesome! A few minutes drive from the parkland lot at Ramshead. The community kept the roads and parking lots plowed well. Communication from the host was excellent. The condo was very comfortable for our family of 3 (2 adults and 4 yr old) and exactly as described. Great spot to relax after our days skiing! We would definitely come back!"
United States
Elizabeth C.
The price is AED 1,099
AED 2,347 total
includes taxes & fees
1 Jun - 2 Jun
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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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Top Rutland Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"The hotel was reasonably well maintianed and had a decent breakfast bar."
Matthew 1-night trip
Posted 11 hours ago
Days Inn by Wyndham Rutland/Killington Area