A winding road surrounded by autumn foliage.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Rutland vacation homes

Dining

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 688 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Rutland Retreat
Private kitchen

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 340
AED 841 total
includes taxes & fees
27 Sep - 28 Sep
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Dining

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

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 582
AED 1,575 total
includes taxes & fees
27 Sep - 28 Sep
large ski ranch hot tub close to killington pets ok
Microwave, oven, stovetop, dishwasher

4. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AED 1,377
AED 2,555 total
includes taxes & fees
27 Sep - 28 Sep
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Property grounds

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 2,077
AED 4,912 total
includes taxes & fees
9 Oct - 10 Oct
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
TV, fireplace, music library, video library

6. 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 AED 1,616
AED 4,419 total
includes taxes & fees
9 Oct - 10 Oct
Cortina Mountain Chalet - Outdoor Hot Tub - Close to Pico and Killington Mountains
Coffee/tea maker, fridge, microwave, oven

7. 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
29 Sep - 30 Sep
4BR Home | Walk Downtown Rutland + Trails
TV, stereo

8. 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 AED 601
AED 1,658 total
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
Exterior detail

9. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is AED 321
AED 1,042 total
includes taxes & fees
29 Sep - 30 Sep
Luxury Condo Tucked in the Heart of Killington
Interior

10. 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 AED 495
AED 995 total
includes taxes & fees
1 Oct - 2 Oct
CozyDen - AC, Bike to Mountain, Porch!
TV, fireplace, Netflix, foosball

11. 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.
The price is AED 1,487
AED 3,549 total
includes taxes & fees
27 Sep - 28 Sep
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Exterior

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, (36 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 727
AED 1,386 total
includes taxes & fees
27 Sep - 28 Sep
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Children's area

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, (71 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is AED 978
AED 3,089 total
includes taxes & fees
28 Sep - 29 Sep
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Property grounds

14. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is AED 983
AED 2,708 total
includes taxes & fees
29 Sep - 30 Sep
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
TV, streaming services, music library, video library

15. 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.
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
TV

16. 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 1,235
AED 3,043 total
includes taxes & fees
28 Sep - 29 Sep
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Smart TV, offices

17. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,315
AED 2,974 total
includes taxes & fees
27 Sep - 28 Sep
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Desk, WiFi, bed sheets

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AED 602
AED 3,441 total
includes taxes & fees
28 Sep - 29 Sep
Slopeside Estate Guesthouse: Hot tub, AC, Grill
Interior

19. 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 489
AED 2,129 total
includes taxes & fees
27 Sep - 28 Sep
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

20. 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 489
AED 2,009 total
includes taxes & fees
27 Sep - 28 Sep
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. Everything was great."
Sherry 1-night trip
Posted 7 hours ago
Emrose Luxury Cabins