A winding road surrounded by autumn foliage.

Search Vacation Homes in Rutland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rutland vacation 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 AED 305
AED 620 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 327
AED 810 total
includes taxes & fees
4 Nov - 5 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 AED 539
AED 592 total
includes taxes & fees
4 Nov - 5 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 AED 526
AED 1,524 total
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 AED 575
AED 1,906 total
includes taxes & fees
4 Nov - 5 Nov
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

6. 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 3,318 total
includes taxes & fees
8 Nov - 9 Nov
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

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 AED 1,550
AED 2,777 total
includes taxes & fees
3 Dec - 4 Dec
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 AED 661
AED 1,331 total
includes taxes & fees
4 Nov - 5 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 AED 291
AED 952 total
includes taxes & fees
4 Nov - 5 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 AED 490
AED 986 total
includes taxes & fees
9 Nov - 10 Nov
CozyDen- Fireplace, Ski Off/ Shuttle On

11. 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 552
AED 1,317 total
includes taxes & fees
4 Nov - 5 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

12. 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.
The price is AED 768
AED 2,480 total
includes taxes & fees
11 Nov - 12 Nov
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AED 724
AED 3,574 total
includes taxes & fees
4 Nov - 5 Nov
Slopeside Estate Guesthouse: Hot tub, AC, Grill

14. 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 AED 473
AED 1,979 total
includes taxes & fees
4 Nov - 5 Nov
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

15. 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 clean and comfortable. Would definitely rent again!"
United States
Molly T.
The price is AED 496
AED 1,063 total
includes taxes & fees
4 Nov - 5 Nov
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

16. 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.

17. 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
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

18. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
United States
Gifford F.
The price is AED 690
AED 1,754 total
includes taxes & fees
4 Nov - 5 Nov
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

19. 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 2,248 total
includes taxes & fees
4 Nov - 5 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

20. 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 AED 708
AED 1,729 total
includes taxes & fees
4 Nov - 5 Nov
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Rutland Hotel Reviews