A winding road surrounded by autumn foliage.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Rutland vacation homes

A dining table set with plates, glasses, and a vase with a plant.

1. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is AED 349
AED 705 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Rutland Retreat
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

2. 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 327
AED 851 total
includes taxes & fees
1 Nov - 2 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A bedroom with a bed, a framed collage, a window with floral curtains, and a striped rug.

3. Cozy 2 Bedroom Suite walking distance to downtown

Cozy 2 Bedroom Suite walking distance to downtown
Rutland
The price is AED 551
AED 641 total
includes taxes & fees
12 Oct - 13 Oct
Cozy 2 Bedroom Suite walking distance to downtown
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

4. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (9 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 639
AED 1,752 total
includes taxes & fees
3 Nov - 4 Nov
large ski ranch hot tub close to killington pets ok
A rustic cabin with a stone fire pit, wooden deck, and a chimney.

5. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
Mendon
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful mountain home in a peaceful setting. Very thoughtfully designed and well maintained with everything you need to have a quiet getaway."
United States
Heidi S.
The price is AED 861
AED 3,645 total
includes taxes & fees
3 Nov - 4 Nov
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

6. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

7. 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
13 Oct - 14 Oct
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

8. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Rutland
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a large group to enjoy Rutland, Killington, and the surrounding area. Plenty of beds for everyone, and bathrooms so no one felt cramped whatsoever. Beautiful home and safe neighborhood. All around a great stay. If we come back for the US Open of MTB next year, this house would be high on our list to stay in again."
United States
Matthew T.
The price is AED 1,341
AED 3,009 total
includes taxes & fees
12 Oct - 13 Oct
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A modern kitchen with stainless steel appliances, a dining table, and a wooden floor.

9. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (7 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 724
AED 1,480 total
includes taxes & fees
9 Nov - 10 Nov
4BR Home | Walk Downtown Rutland + Trails
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

10. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
The price is AED 355
AED 1,087 total
includes taxes & fees
3 Nov - 4 Nov
Luxury Condo Tucked in the Heart of Killington
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

11. CozyDen- Location, Ski Off/ Shuttle On

CozyDen- Location, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
CozyDen- Location, Ski Off/ Shuttle On
A two-story house with a covered porch and a gabled roof.

12. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.0 out of 10, Wonderful, (37 reviews)
"Very nice house to stay in Fair Haven VT. Worked perfectly for us and beautiful area. Clean and has everything you need."
United States
Amy G.
The price is AED 496
AED 1,104 total
includes taxes & fees
18 Oct - 19 Oct
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

13. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AED 741
AED 3,789 total
includes taxes & fees
13 Oct - 14 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A compact kitchen with a refrigerator, stove, microwave, and sink.

14. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AED 655
AED 2,093 total
includes taxes & fees
12 Oct - 13 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A cozy room with a wooden ceiling, a large window with a snowy view, a sofa, and a dining table with chairs.

15. Family and friend friendly upper ski cabin with bunks, sleeps 8

Family and friend friendly upper ski cabin with bunks, sleeps 8
Killington
The price is AED 797
AED 2,065 total
includes taxes & fees
12 Oct - 13 Oct
Family and friend friendly upper ski cabin with bunks, sleeps 8
A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

16. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Killington
9.4 out of 10, Exceptional, (6 reviews)
"We had a great time at this property! The hot tub was very clean, and the listing described it very well! "
United States
Briana S.
The price is AED 1,022
AED 2,381 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

17. 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)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 601
AED 2,288 total
includes taxes & fees
14 Oct - 15 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

18. 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 615
AED 2,299 total
includes taxes & fees
12 Oct - 13 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, a dining table with chairs, and a hanging light fixture.

19. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved this house. Our stay was perfect. It was so close to the mountain and all the restaurants. It was not on a busy street, so private and clean and overall amazing place to stay. We would definitely choose to stay again here!!"
United States
Sandra G.
The price is AED 872
AED 2,463 total
includes taxes & fees
14 Oct - 15 Oct
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 907
AED 2,702 total
includes taxes & fees
13 Oct - 14 Oct
The Tower House | Hot Tub | Firepit | Dog-Friendly
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Breakfast very good"
Sonia G 1-night trip
Posted 7 hours ago
Mountain Meadows Lodge