A winding road surrounded by autumn foliage.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Rutland holiday homes

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

1. 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 £179
includes taxes & fees
29 Sept - 30 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A dining table set with plates, glasses, and a vase with a plant.

2. 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 £147
includes taxes & fees
28 Oct - 29 Oct
Cozy Rutland Retreat
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

3. 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 £361
includes taxes & fees
5 Oct - 6 Oct
large ski ranch hot tub close to killington pets ok
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

4. 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.
The price is £401
includes taxes & fees
29 Sept - 30 Sept
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.

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is £546
includes taxes & fees
29 Sept - 30 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

6. 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 £611
includes taxes & fees
29 Sept - 30 Sept
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A rustic cabin with a stone fire pit, wooden deck, and a chimney.

7. 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 £1,075
includes taxes & fees
9 Oct - 10 Oct
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
A spacious living room with a high ceiling, a fireplace, and a dining area with a chandelier.

8. Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains

Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
Mendon
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was great and well taken care of. The location was superb!"
United States
Juan P.
The price is £975
includes taxes & fees
9 Oct - 10 Oct
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
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 £304
includes taxes & fees
26 Oct - 27 Oct
4BR Home | Walk Downtown Rutland + Trails
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is £344
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is £433
includes taxes & fees
29 Sept - 30 Sept
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

12. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is £214
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
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 £733
includes taxes & fees
5 Oct - 6 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
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.

14. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is £215
includes taxes & fees
1 Oct - 2 Oct
CozyDen - AC, Bike to Mountain, Porch!
Winter Wonderland

15. 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 £431
includes taxes & fees
29 Sept - 30 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
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.

16. 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 £455
includes taxes & fees
30 Sept - 1 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

17. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Great property to stay at highly recommend and will hopefully be staying again soon!"
United States
Robert R.
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

18. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is £371
includes taxes & fees
29 Sept - 30 Sept
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

19. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
The price is £352
includes taxes & fees
29 Sept - 30 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

20. Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.

Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Killington
7.6 out of 10, Good, (4 reviews)
"Great location, clean and quiet."
United States
Dr. Stephan B.
The price is £429
includes taxes & fees
29 Sept - 30 Sept
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Spacious suite. Good kitchen. Great scenery"
Ilya 4-night trip
Posted less than an hour ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Rutland

Rutland Holiday Homes information

Number of reviews
61
Accommodation
884 Holiday Homes
Lowest Price
£147
Highest Price
£1,075