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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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 £175
includes taxes & fees
19 Jul - 20 Jul
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 £316
includes taxes & fees
12 Jul - 13 Jul
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, (5 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 £348
includes taxes & fees
7 Jul - 8 Jul
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 £553
includes taxes & fees
30 Jun - 1 Jul
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
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 £539
includes taxes & fees
30 Jun - 1 Jul
Breakaway House by Killington Vacation Rentals
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, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is £381
includes taxes & fees
30 Jun - 1 Jul
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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 £207
includes taxes & fees
30 Jun - 1 Jul
CozyDen - AC, Grill, Bike to Mountain, Porch!
Exterior

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
8.8 out of 10, Excellent, (30 reviews)
"Great house conveniently located, excellent communication with owner!"
United States
Kim C.
The price is £268
includes taxes & fees
1 Jul - 2 Jul
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
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 £565
includes taxes & fees
30 Jun - 1 Jul
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Fridge, microwave, oven, stovetop

Feel the real VT! Lakes, hikes, a foodies delight!

Feel the real VT! Lakes, hikes, a foodies 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 £436
includes taxes & fees
30 Jun - 1 Jul
Feel the real VT! Lakes, hikes, a foodies delight!
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (15 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is £301
includes taxes & fees
30 Jun - 1 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
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, (86 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
The price is £250
includes taxes & fees
30 Jun - 1 Jul
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
TV, fireplace, Netflix, table football

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, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is £554
includes taxes & fees
30 Jun - 1 Jul
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy with a working hot tub. Would highly recommend"
United States
Justin E.
The price is £291
includes taxes & fees
1 Jul - 2 Jul
Cozy Moonship Yurt in the woods
Fridge, microwave, oven, stovetop

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, (111 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is £317
includes taxes & fees
1 Jul - 2 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
TV, fireplace, video games, table football

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, (69 reviews)
"Great stay. Killer location!"
United States
Matthew P.
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
TV

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 £472
includes taxes & fees
30 Jun - 1 Jul
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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 £521
includes taxes & fees
30 Jun - 1 Jul
The Tower House | Hot Tub | Firepit | Dog-Friendly
Property grounds

Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
Modern Farm House…minutes to Okemo; 2 King beds!
Smart TV

Family and friend friendly upper ski cabin with bunks, sleeps 8

Family and friend friendly upper ski cabin with bunks, sleeps 8
Killington
Family and friend friendly upper ski cabin with bunks, sleeps 8
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"The room was very large and had a lovely view of the grounds and river. And having a grocery store across the street was a plus. I do have two suggestions. First, the room was not well lit. As I said, the room was quite spacious, but only had two small lamps so it was quite dim. There were many electrical outlets, so a couple of stand lamps would be great and not very expensive. Second, there was a lot of open space in the room, so a small table and chairs would have been great as we ate dinner in the room. I ended up carrying in a table from outside to have a place to eat and use my computer."
Philip 1-night trip
Posted 10 hours ago
The Shire Woodstock

Find out more about Rutland

Rutland Holiday Homes information

Number of reviews
426
Accommodation
897 Holiday Homes
Lowest Price
£175
Highest Price
£565