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

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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. 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 £132
includes taxes & fees
14 Sept - 15 Sept
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 £176
includes taxes & fees
26 Aug - 27 Aug
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

3. 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 £457
includes taxes & fees
26 Aug - 27 Aug
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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.

4. 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 £395
includes taxes & fees
26 Aug - 27 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock

5. 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 £419
includes taxes & fees
26 Aug - 27 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
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
The price is £450
includes taxes & fees
26 Aug - 27 Aug
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

7. 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 £499
includes taxes & fees
30 Aug - 31 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

8. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is £522
includes taxes & fees
26 Aug - 27 Aug
Breakaway House by Killington Vacation Rentals
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.

9. 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 £200
includes taxes & fees
26 Aug - 27 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
A cozy living room with a fireplace, a television, and a view of a snowy deck.

10. 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, (58 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is £523
includes taxes & fees
27 Aug - 28 Aug
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A spacious living area with a fireplace, a television, and a dining area with natural light.

11. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is £403
includes taxes & fees
26 Aug - 27 Aug
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

12. 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 £484
includes taxes & fees
26 Aug - 27 Aug
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
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, (5 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is £348
includes taxes & fees
6 Sept - 7 Sept
large ski ranch hot tub close to killington pets ok

14. 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, (70 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is £549
includes taxes & fees
26 Aug - 27 Aug
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A modern house with a stone facade, a large deck, and outdoor seating.

15. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
United States
SHEEPDOG 1.
The price is £574
includes taxes & fees
26 Aug - 27 Aug
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

16. Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is £457
includes taxes & fees
27 Aug - 28 Aug
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
A modern living room with a fireplace, a dining area, and a kitchen.

17. 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 £690
includes taxes & fees
26 Aug - 27 Aug
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

18. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
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 £293
includes taxes & fees
22 Sept - 23 Sept
4BR Home | Walk Downtown Rutland + Trails
A spacious living room with a stone fireplace, large windows, and a cozy seating area.

19. 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 £812
includes taxes & fees
26 Aug - 27 Aug
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
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.

20. 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 £285
includes taxes & fees
6 Sept - 7 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!
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

Middlebury Inn

Middlebury Inn

10/10 Excellent
"Another absolutely excellent stay! I've stayed a couple of nights on 12 seperate occasions.One of my favorite places to stay anywhere. I've stayed in 40+ states, 12 countries, and a couple of protectorates across 4 continents. Friendly and accommendating staff who are of great service. Could not recommend highly enough, especially because of their pet policy. Thank you!"
sean 2-night trip
Posted 2 hours ago
Middlebury Inn

Find out more about Chittenden

Chittenden Holiday Homes information

Number of reviews
205
Accommodation
660 Holiday Homes
Lowest Price
£132
Highest Price
£812