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Our top choices for Rutland holiday homes

1. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (18 reviews)
"WE ENJOYED OUR STAY"
United States
Susan E.
The price is £136
includes taxes & fees
30 Nov - 1 Dec
Cozy Rutland Retreat

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
9.4 out of 10, Exceptional, (8 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 £211
includes taxes & fees
15 Nov - 16 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

3. Kingsley Homestead - 2 Bedroom retreat

Kingsley Homestead - 2 Bedroom retreat
Rutland
The price is £140
includes taxes & fees
18 Nov - 19 Nov
Kingsley Homestead - 2 Bedroom retreat

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, (10 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is £389
includes taxes & fees
15 Nov - 16 Nov
large ski ranch hot tub close to killington pets ok

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 £467
includes taxes & fees
16 Nov - 17 Nov
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

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 £646
includes taxes & fees
15 Nov - 16 Nov
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

7. 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 £525
includes taxes & fees
14 Nov - 15 Nov
Relaxing Rutland Retreat Near Skiing, Dining & Hiking

8. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (8 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 £264
includes taxes & fees
14 Nov - 15 Nov
4BR Home | Walk Downtown Rutland + Trails

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 £177
includes taxes & fees
15 Nov - 16 Nov
Luxury Condo Tucked in the Heart of Killington

10. CozyDen- Fireplace, Ski Off/ Shuttle On

CozyDen- Fireplace, 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 £203
includes taxes & fees
15 Nov - 16 Nov
CozyDen- Fireplace, Ski Off/ Shuttle On

11. 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)
"Great quick stay on the way to the Adirondacks"
United States
Natalie B.
The price is £214
includes taxes & fees
15 Nov - 16 Nov
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay but there was some noise in the bigger bedroom from the heating panels so the sleep was disturbed. Other than this, we had a great time at the accommodation."
Canada
Smriti
The price is £408
includes taxes & fees
15 Nov - 16 Nov
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is £751
includes taxes & fees
16 Nov - 17 Nov
Slopeside Estate Guesthouse: Hot tub, AC, Grill

14. 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 £522
includes taxes & fees
15 Nov - 16 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

15. Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Killington
The price is £409
includes taxes & fees
15 Nov - 16 Nov
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

16. 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

17. 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 £276
includes taxes & fees
15 Nov - 16 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is £469
includes taxes & fees
15 Nov - 16 Nov
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

19. 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
9.0 out of 10, Wonderful, (7 reviews)
"Loved the quiet seclusion of the Shack, but also that we were close to hikes, lakes, markets, and food. We had a wonderful and relaxing stay!!"
United States
Sarah G.
The price is £420
includes taxes & fees
15 Nov - 16 Nov
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

20. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is £413
includes taxes & fees
15 Nov - 16 Nov
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
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.

Learn more about Rutland

Nestled in the Green Mountains, this charming city offers world-class skiing and a vibrant university atmosphere. Catch a show at the historic Paramount Theatre or explore nature's wonders at McLaughlin Falls and Green Mountain National Forest.

A forest with autumn foliage and a distant view of a town.

Top reviews in Rutland