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

Search Vacation Homes in Chittenden

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chittenden vacation homes

In-room safe, iron/ironing board, WiFi, bed sheets

1. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is ￥13,747
￥45,016 total
includes taxes & fees
Aug 16 - Aug 17
Luxury Condo Tucked in the Heart of Killington
TV, fireplace, DVD player, table tennis

2. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is ￥66,526
￥137,260 total
includes taxes & fees
Aug 31 - Sep 1
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Dining

3. 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
9.2 out of 10, Wonderful, (5 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.
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Coffee/tea maker, fridge, microwave, oven

4. 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 ￥33,313
￥119,336 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Private kitchen

5. 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 ￥14,764
￥37,560 total
includes taxes & fees
Aug 17 - Aug 18
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Exterior

6. 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 ￥23,816
￥96,838 total
includes taxes & fees
Aug 16 - Aug 17
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

7. 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 ￥23,816
￥96,838 total
includes taxes & fees
Aug 16 - Aug 17
Ski Home/Arcade Mountain Views Near Killington/Woodstock
TV, offices

8. 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 ￥31,081
￥107,526 total
includes taxes & fees
Aug 17 - Aug 18
The Tower House | Hot Tub | Firepit | Dog-Friendly
Dining

9. 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 ￥28,095
￥76,381 total
includes taxes & fees
Aug 16 - Aug 17
large ski ranch hot tub close to killington pets ok
House, 6 Bedrooms | Living area

10. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is ￥41,517
￥124,598 total
includes taxes & fees
Aug 16 - Aug 17
Breakaway House by Killington Vacation Rentals
Smart TV

11. 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
Smart TV, fireplace

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 ￥51,999
￥106,928 total
includes taxes & fees
Aug 24 - Aug 25
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Interior

13. 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 ￥32,707
￥72,515 total
includes taxes & fees
Aug 25 - Aug 26
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Smart TV, fireplace, video games, stereo

14. 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)
"Great location and excellent hosts "
United States
Peter G.
The price is ￥40,326
￥105,545 total
includes taxes & fees
Aug 20 - Aug 21
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Coffee/tea maker, fridge, microwave, oven

15. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved this house. Our stay was perfect. It was so close to the mountain and all the restaurants. It was not on a busy street, so private and clean and overall amazing place to stay. We would definitely choose to stay again here!!"
United States
Sandra G.
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Coffee/tea maker, fridge, microwave, oven

16. 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 ￥52,529
￥122,265 total
includes taxes & fees
Sep 9 - Sep 10
Feel the real VT! Lakes, hikes, a foodies delight!
Interior

17. 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 ￥68,658
￥138,312 total
includes taxes & fees
Aug 19 - Aug 20
Snowarts- Game room, Fireplace, Close to golf!
Smart TV, fireplace

18. 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 ￥74,703
￥152,061 total
includes taxes & fees
Aug 19 - Aug 20
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Terrace/patio

19. 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 ￥53,816
￥110,119 total
includes taxes & fees
Sep 1 - Sep 2
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

20. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is ￥51,985
￥102,064 total
includes taxes & fees
Aug 18 - Aug 19
Killington A-frame 2 Bedroom Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chittenden Hotel Reviews

Lake Bomoseen Lodge

Lake Bomoseen Lodge

10/10 Excellent
"Peaceful lake view "
Noreen 2-night trip
Posted 16 hours ago
Lake Bomoseen Lodge

Find out more about Chittenden

Chittenden Vacation Homes information

Number of reviews
50
Accommodation
660 Vacation Homes
Lowest Price
￥72,515
Highest Price
￥152,061