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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chittenden vacation homes

A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

1. 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 AED 575
AED 2,005 total
includes taxes & fees
15 Oct - 16 Oct
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A spacious living room with a fireplace, a television, and a large window.

2. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is AED 898
AED 2,735 total
includes taxes & fees
15 Oct - 16 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
The price is AED 342
AED 1,069 total
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo Tucked in the Heart of Killington
A dining table set with plates, glasses, and a vase with a plant.

4. 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 AED 338
AED 694 total
includes taxes & fees
20 Oct - 21 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.

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 AED 327
AED 851 total
includes taxes & fees
1 Nov - 2 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

6. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
10.0 out of 10, Exceptional, (2 reviews)
"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...
United States
Heidi P.
The price is AED 943
AED 2,654 total
includes taxes & fees
15 Oct - 16 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A bedroom with a bed, a framed collage, a window with floral curtains, and a striped rug.

7. Cozy 2 Bedroom w/whirlpool tub close distance to downtown.

Cozy 2 Bedroom w/whirlpool tub close distance to downtown.
Rutland
The price is AED 606
AED 705 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 2 Bedroom w/whirlpool tub close distance to downtown.
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.

8. 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 AED 594
AED 2,276 total
includes taxes & fees
18 Oct - 19 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

9. 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 AED 594
AED 2,276 total
includes taxes & fees
18 Oct - 19 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

10. 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 AED 726
AED 2,347 total
includes taxes & fees
18 Oct - 19 Oct
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 907
AED 2,723 total
includes taxes & fees
15 Oct - 16 Oct
The Tower House | Hot Tub | Firepit | Dog-Friendly
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.

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

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful house! It had everything we needed for a fun and relaxing week. "
United States
Joshua
The price is AED 521
AED 1,565 total
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

13. 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, (9 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AED 639
AED 1,752 total
includes taxes & fees
3 Nov - 4 Nov
large ski ranch hot tub close to killington pets ok
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

14. 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 Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A rustic cabin with a stone fire pit, wooden deck, and a chimney.

15. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
Mendon
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful mountain home in a peaceful setting. Very thoughtfully designed and well maintained with everything you need to have a quiet getaway."
United States
Heidi S.
Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.
A spacious living room with a stone fireplace, large windows, and a cozy seating area.

16. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Killington
10.0 out of 10, Exceptional, (3 reviews)
"great rental overall, the unit was well stocked, clean and have everything you need for your stay."
United States
matt d.
The price is AED 1,936
AED 4,439 total
includes taxes & fees
18 Oct - 19 Oct
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
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.

17. CozyDen- Location, Ski Off/ Shuttle On

CozyDen- Location, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
21 Oct - 22 Oct
CozyDen- Location, Ski Off/ Shuttle On
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

18. 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 AED 1,328
AED 2,932 total
includes taxes & fees
15 Oct - 16 Oct
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A wooden cabin with a hot tub in a corner, a sliding glass door leading to a living area, and a window with a view of greenery.

19. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"This company was professional and clear with their communication, very accommodating when we had to change plans. The house was in great shape and stocked with everything we needed"
United States
Kyle L.
The price is AED 1,714
AED 3,671 total
includes taxes & fees
18 Oct - 19 Oct
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
A cozy living room with a fireplace, a sofa set, and a stone wall.

20. Bearmont- Pool, HotTub, Fireplace

Bearmont- Pool, HotTub, Fireplace
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 AED 1,182
AED 2,442 total
includes taxes & fees
15 Oct - 16 Oct
Bearmont- Pool, HotTub, Fireplace
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Convenient location, however we arrived at the hotel late and there were no lights from the main road leading to the hotel ao we missed the driveway/entrance. Pillows were too hard."
Mary Ann 1-night trip
Posted 9 hours ago
My Place Hotel-Randolph VT