A lakeside community with houses and docks.

Holiday Homes in Castleton

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Castleton holiday homes

A dining table set with plates, glasses, and a vase with a plant.

1. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is AU$275
includes taxes & fees
26 Oct - 27 Oct
Cozy Rutland Retreat
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

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
9.8 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$340
includes taxes & fees
28 Sept - 29 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A two-story house with a covered porch and a gabled roof.

3. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.0 out of 10, Wonderful, (36 reviews)
"Very nice house to stay in Fair Haven VT. Worked perfectly for us and beautiful area. Clean and has everything you need."
United States
Amy G.
The price is AU$537
includes taxes & fees
30 Sept - 1 Oct
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

4. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is AU$619
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

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 AU$779
includes taxes & fees
28 Sept - 29 Sept
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

6. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$637
includes taxes & fees
28 Sept - 29 Sept
large ski ranch hot tub close to killington pets ok
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AU$817
includes taxes & fees
28 Sept - 29 Sept
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

8. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is AU$410
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

9. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"Clean comfy quiet spot."
United States
Dillon B.
The price is AU$336
includes taxes & fees
26 Oct - 27 Oct
Peaceful 1-bedroom bungalow with AC in charming Wells
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AU$1,359
includes taxes & fees
28 Sept - 29 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

11. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is AU$1,030
includes taxes & fees
28 Sept - 29 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

12. 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$830
includes taxes & fees
27 Sept - 28 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock

13. 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$837
includes taxes & fees
28 Sept - 29 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

14. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
CozyDen - AC, Bike to Mountain, Porch!
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

15. 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 AU$1,045
includes taxes & fees
27 Sept - 28 Sept
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

16. 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 AU$1,153
includes taxes & fees
28 Sept - 29 Sept
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

17. 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 AU$701
includes taxes & fees
28 Sept - 29 Sept
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is AU$697
includes taxes & fees
28 Sept - 29 Sept
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

19. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
The price is AU$661
includes taxes & fees
28 Sept - 29 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A modern kitchen with stainless steel appliances, a dining table, and a wooden floor.

20. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (7 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$555
includes taxes & fees
29 Sept - 30 Sept
4BR Home | Walk Downtown Rutland + Trails
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 Castleton Hotel Reviews

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. Everything was great."
Sherry 1-night trip
Posted 5 hours ago
Emrose Luxury Cabins

Find out more about Castleton

Castleton Holiday Homes information

Number of reviews
90
Accommodation
552 Holiday Homes
Lowest Price
AU$275
Highest Price
AU$1,359