A winding road surrounded by autumn foliage.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 338
AED 694 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Rutland Retreat
A small, enclosed room with wooden walls and a single electric heater on a stone base.

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 house with a wooden deck, a pink flamingo decoration, and a small garden with green plants.

3. Cozy 2 Bedroom w/whirlpool tub close distance to downtown.

Cozy 2 Bedroom w/whirlpool tub close distance to downtown.
Rutland
The price is AED 533
AED 620 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom w/whirlpool tub close 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 720
AED 1,855 total
includes taxes & fees
16 Nov - 17 Nov
large ski ranch hot tub close to killington pets ok
A spacious living room with a sofa, armchair, ottoman, and a television on a stand.

5. 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 AED 575
AED 2,005 total
includes taxes & fees
19 Oct - 20 Oct
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.

6. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,377
AED 2,703 total
includes taxes & fees
19 Oct - 20 Oct
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

7. 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 1,328
AED 2,994 total
includes taxes & fees
18 Oct - 19 Oct
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A two-story house with a covered porch and a car parked in front.

8. 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 727
AED 1,484 total
includes taxes & fees
16 Nov - 17 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.

9. 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 406
AED 1,147 total
includes taxes & fees
28 Oct - 29 Oct
Luxury Condo Tucked in the Heart of Killington
A cozy living room with a fireplace, a television, and a view of a snowy deck.

10. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
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.
The price is AED 463
AED 1,000 total
includes taxes & fees
21 Oct - 22 Oct
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
9.2 out of 10, Wonderful, (39 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 1,116 total
includes taxes & fees
18 Oct - 19 Oct
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
A forested area with a wooden structure and a red and blue playset.

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Killington
9.6 out of 10, Exceptional, (72 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is AED 642
AED 2,797 total
includes taxes & fees
18 Oct - 19 Oct
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A bedroom with a large bed, a sofa, a desk, and two windows.

14. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods
The price is AED 539
AED 1,340 total
includes taxes & fees
16 Nov - 17 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
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.

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
10.0 out of 10, Exceptional, (1 review)
"The only struggle was we got on late at night. We couldn’t find the driveway and then it said the lower, condo we did not realize we had to go downstairs. But once found it everything was great. It was a fully functioning kitchen, towels, soaps, clean and even a working grill with a beautiful view to sit on the porch. We would rent again!"
United States
Annette G.
The price is AED 686
AED 1,828 total
includes taxes & fees
18 Oct - 19 Oct
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A compact kitchen with a refrigerator, stove, microwave, and sink.

16. 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
18 Oct - 19 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

18. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AED 726
AED 2,347 total
includes taxes & fees
18 Oct - 19 Oct
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A spacious living room with a fireplace, a television, and a large window.

19. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is AED 898
AED 2,714 total
includes taxes & fees
18 Oct - 19 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
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.

20. 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 391
AED 2,019 total
includes taxes & fees
18 Oct - 19 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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

Turn of River Lodge

Turn of River Lodge

10/10 Excellent
"We stayed here last minute on our way through. The owner was delightful to talk to about the area. Rooms were clean and the breakfast was just right for us including homemade donuts and muffins. The only downfall was the stairs as we are both in our sixties."
Deb 1-night trip
Posted 6 hours ago
Turn of River Lodge