Holiday Homes in Rutland

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 June - 28 June
In three months
24 July - 26 July
In four months
21 Aug - 23 Aug

Our top choices for Rutland holiday homes

Private kitchen

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 AU$335
includes taxes & fees
29 Apr - 30 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$604
includes taxes & fees
29 Apr - 30 Apr
large ski ranch hot tub close to killington pets ok
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (4 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 AU$594
includes taxes & fees
29 Apr - 30 Apr
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Microwave, oven, stovetop, dishwasher

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AU$876
includes taxes & fees
29 Apr - 30 Apr
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AU$423
includes taxes & fees
29 Apr - 30 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AU$438
includes taxes & fees
10 May - 11 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is AU$774
includes taxes & fees
29 Apr - 30 Apr
Large Killington Area Home | Sleeps 7 | Game Room
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$378
includes taxes & fees
29 Apr - 30 Apr
CozyDen - AC, Grill, Bike to Mountain, Porch!
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is AU$826
includes taxes & fees
30 Apr - 1 May
New Ludlow Village Home with Stunning Okemo Mountain View
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AU$900
includes taxes & fees
29 Apr - 30 Apr
The Tower House | Hot Tub | Firepit | Dog-Friendly
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AU$978
includes taxes & fees
29 Apr - 30 Apr
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"Very easy check in and out and clean home. Streets nearby can be hard to travel without 4 wheel drive. "
United States
Andrew O.
The price is AU$670
includes taxes & fees
29 Apr - 30 Apr
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AU$1,068
includes taxes & fees
29 Apr - 30 Apr
Breakaway House by Killington Vacation Rentals
Fridge, microwave, oven, stovetop

Feel the real VT! Ski Killington and a foodie’s delight!

Feel the real VT! Ski Killington and a foodie’s delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."
United States
Rebecca
The price is AU$776
includes taxes & fees
11 May - 12 May
Feel the real VT! Ski Killington and a foodie’s delight!
Smart TV, fireplace, video games, stereo

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (19 reviews)
"A very pleasant stay at this place. Nice furnishings, everything clean, the hot tub was utilized. Would recommend this to any group or family seeking nearby cozy accommodations near the slopes. "
United States
Tom W.
The price is AU$911
includes taxes & fees
29 Apr - 30 Apr
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
TV, fireplace, table football, stereo

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is AU$641
includes taxes & fees
29 Apr - 30 Apr
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Outdoor spa tub

Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great hosts with a great location to Killington"
United States
Ed P.
Walk to Pickle Barrel & Jax. Hot tub & Views
Exterior detail

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit

Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit
Castleton
9.0 out of 10, Wonderful, (12 reviews)
"Very nice property, beautiful time of year to visit Vermont. Colors were wonderful."
United States
Teresa V.
The price is AU$995
includes taxes & fees
1 May - 2 May
Pastoral, dog-friendly home surrounded by lush woodland with free WiFi & firepit
Interior

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 AU$765
includes taxes & fees
29 Apr - 30 Apr
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

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 AU$765
includes taxes & fees
29 Apr - 30 Apr
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

On The River Inn

On The River Inn

10/10 Excellent
"I was at the inn for one night only, and I really enjoyed it. It's very clean and pleasant. My room was spacious, comfortable, and had a lovely view toward the river. The fire pit under a starry night was magical. The only part of the experience that left to be desired was the breakfast. It was unremarkable."
Claudio 1-night trip
Posted 9 hours ago
On The River Inn

Find out more about Rutland

Rutland Holiday Homes information

Number of reviews
225
Accommodation
903 Holiday Homes
Lowest Price
AU$335
Highest Price
AU$1,068