A calm lake reflecting colorful autumn trees and a clear blue sky.

Holiday Homes in Chittenden

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chittenden holiday homes

1. 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$828
includes taxes & fees
31 Aug - 1 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

2. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
The price is AU$243
includes taxes & fees
14 Sept - 15 Sept
Cozy Rutland Retreat

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is AU$377
includes taxes & fees
30 Aug - 31 Aug
Luxury Condo Tucked in the Heart of Killington
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

4. 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$325
includes taxes & fees
8 Sept - 9 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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.

5. 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$809
includes taxes & fees
30 Aug - 31 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

6. 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$938
includes taxes & fees
30 Aug - 31 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
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.

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

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$374
includes taxes & fees
30 Aug - 31 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

8. 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, (5 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$643
includes taxes & fees
6 Sept - 7 Sept
large ski ranch hot tub close to killington pets ok
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

9. 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, (20 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is AU$922
includes taxes & fees
1 Sept - 2 Sept
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
A modern living room with a fireplace, a dining area, and a kitchen.

10. Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
The price is AU$1,283
includes taxes & fees
1 Sept - 2 Sept
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
A stone fireplace with a black mantel, framed picture, and decorative items.

11. Snowarts- Game room, Fireplace, Close to golf!

Snowarts- Game room, Fireplace, Close to golf!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
United States
Tammy W.
The price is AU$1,164
includes taxes & fees
2 Sept - 3 Sept
Snowarts- Game room, Fireplace, Close to golf!
A cozy living room with a stone fireplace, a sofa set, and a dining table.

12. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
The price is AU$926
includes taxes & fees
31 Aug - 1 Sept
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
A cozy living room with a leather sofa, a wooden coffee table, and a large plant.

13. HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
The price is AU$740
includes taxes & fees
1 Sept - 2 Sept
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
A two-story wooden cabin with a balcony, illuminated windows, and a front door.

14. BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (13 reviews)
"Place was perfect for us for a group ski weekend."
United States
Kevin F.
The price is AU$1,157
includes taxes & fees
1 Sept - 2 Sept
BearRight- AC, Pool, Hot Tub, Grill, FirePit
A covered porch with a grill, two Adirondack chairs, and a fire pit.

15. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Great communication with host. I highly recommend this home, and will definitely book again."
United States
Edward M.
The price is AU$936
includes taxes & fees
1 Sept - 2 Sept
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
A spacious kitchen with a central island, wooden ceiling, and large windows.

16. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is AU$1,180
includes taxes & fees
31 Aug - 1 Sept
Hot Tub Getaway - Near Killington - Sleeps 12
A room with a large window overlooking a body of water and trees, a wooden floor lamp, and a green sofa with cushions.

17. Stunning Pet Friendly House with Pond View, Sauna and Jetted Tub in the Home

Stunning Pet Friendly House with Pond View, Sauna and Jetted Tub in the Home
The Woods
The price is AU$894
includes taxes & fees
13 Sept - 14 Sept
Stunning Pet Friendly House with Pond View, Sauna and Jetted Tub in the Home
A red barn in a forested area with mountains in the background.

18. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
Ripton
9.8 out of 10, Exceptional, (6 reviews)
"The property was very generously provisioned, pet friendly, clean and comfortable."
United States
Lani C.
Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
A bedroom with a bed, two bedside lamps, and a large window with a mountain view.

19. BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS

BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS
Killington
10.0 out of 10, Exceptional, (15 reviews)
The price is AU$1,113
includes taxes & fees
31 Aug - 1 Sept
BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

20. 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 AU$672
includes taxes & fees
29 Aug - 30 Aug
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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 Chittenden Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"This place was set up even better than I expected. With nature right outside the door, it was so relaxing and stress-free, and the overall atmosphere was elegant and beautiful. Staff members are very friendly, too. The only thing was that the mattress was a bit too soft, which gave me a backache."
Hwajung 3-night trip
Posted 1 hour ago
On The River Inn

Find out more about Chittenden

Chittenden Holiday Homes information

Number of reviews
171
Accommodation
672 Holiday Homes
Lowest Price
AU$243
Highest Price
AU$1,283