A mountainous landscape with autumn foliage.

Holiday Homes in Rutland County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Rutland County holiday homes

Townhome, 3 Bedrooms | Private kitchen | Fridge, coffee/tea maker, toaster

Sunrise Mountain Village by RedAwning

Sunrise Mountain Village by RedAwning
2.0 star property
Killington
Sunrise Mountain Village by RedAwning
House, 4 Bedrooms | Living area | Smart TV, streaming services

Serene Architect-designed Vermont Chalet 4 Bedroom Home

Serene Architect-designed Vermont Chalet 4 Bedroom Home
3.0 star property
Pittsfield
Serene Architect-designed Vermont Chalet 4 Bedroom Home
House, 4 Bedrooms | Living area

The Family Retreat At Bomoseen 4 Bedroom Home

The Family Retreat At Bomoseen 4 Bedroom Home
3.0 star property
Castleton
The Family Retreat At Bomoseen 4 Bedroom Home
House, Multiple Beds (Beechwood Home) | Living area

Beechwood Home

Beechwood Home
3.0 star property
Rutland
Beechwood Home
House, 3 Bedrooms | Living area

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
Killington
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
House, Multiple Beds (Viewmont Chalet) | Living area

Viewmont Chalet

Viewmont Chalet
3.5 star property
Killington
Viewmont Chalet
Apartment, Multiple Beds (Colony Club C12) | Interior

Colony Club C12

Colony Club C12
3.5 star property
Killington
Colony Club C12
House, Multiple Beds (Hemlock Ridge 1D) | Interior

Hemlock Ridge 1D

Hemlock Ridge 1D
3.5 star property
Killington
Hemlock Ridge 1D
House, Multiple Beds (Dean Hill Chalet) | Living area

Dean Hill Chalet

Dean Hill Chalet
3.0 star property
Killington
Dean Hill Chalet
House, 1 Double Bed (Pond View Cabin) | Living area

Pond View Cabin

Pond View Cabin
3.0 star property
Rutland
Pond View Cabin
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
House, 4 Bedrooms | Dining

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
3.0 star property
Killington
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
House, 4 Bedrooms | Living area | Smart TV

The Powder House 4 Bedroom Home

The Powder House 4 Bedroom Home
3.0 star property
Killington
The Powder House 4 Bedroom Home
House, 4 Bedrooms | Property grounds

Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home

Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home
3.0 star property
Rutland
Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home
House, 3 Bedrooms | Living area

Shreadquarters 3 Bedroom Home

Shreadquarters 3 Bedroom Home
3.0 star property
Killington
Shreadquarters 3 Bedroom Home
House, Multiple Beds (Zen Box Farm) | Interior

Zen Box Farm

Zen Box Farm
2.5 star property
Bomoseen
Zen Box Farm
House, Multiple Beds (Winter Lore) | Interior

Winter Lore

Winter Lore
3.0 star property
Rutland
Winter Lore
House | 3 bedrooms

Sweet Life in Pittsfield

Sweet Life in Pittsfield
2.0 star property
Pittsfield
Sweet Life in Pittsfield
House, 4 Bedrooms | Living area | Smart TV

Whitetail Chalet 4 Bedroom Home

Whitetail Chalet 4 Bedroom Home
3.0 star property
Killington
Whitetail Chalet 4 Bedroom Home
House, Multiple Beds (Great Escape Ski Lodge) | Property grounds

Great Escape Ski Lodge

Great Escape Ski Lodge
3.0 star property
Killington
Great Escape Ski Lodge
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 County Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"Staff was kind, the rooms needed a bit of an updating."
Shannon 1-night trip
Posted 10 hours ago
Days Inn by Wyndham Rutland/Killington Area

Find out more about Rutland County

Rutland County Holiday Homes information

Number of reviews
Accommodation
94 Holiday Homes
Lowest Price
Rp13.328.588
Highest Price
Rp13.328.588