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
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 Chittenden holiday homes

A bedroom with a bed, curtains, a radiator, and a view of the outside.

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 €176
includes taxes & fees
29 Sept - 30 Sept
Cozy Rutland Retreat

2. 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 €667
includes taxes & fees
7 Oct - 8 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

3. 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 €647
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 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 €211
includes taxes & fees
6 Oct - 7 Oct
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 €472
includes taxes & fees
24 Sept - 25 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

6. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €251
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
A two-story house with a garage, solar panels, and a deck with outdoor furniture.

7. Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games

Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
North Sherburne
9.4 out of 10, Exceptional, (24 reviews)
"House was beautiful & a great getaway for our group! "
United States
GiGi M.
The price is €704
includes taxes & fees
28 Sept - 29 Sept
Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
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.

8. 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 spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

9. 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 €494
includes taxes & fees
4 Oct - 5 Oct
large ski ranch hot tub close to killington pets ok
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

10. 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 €642
includes taxes & fees
24 Sept - 25 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
A modern living room with a fireplace, a dining area, and a kitchen.

11. 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 €839
includes taxes & fees
24 Sept - 25 Sept
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
A stone fireplace with a black mantel, framed picture, and decorative items.

12. 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.
Snowarts- Game room, Fireplace, Close to golf!
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

13. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is €645
includes taxes & fees
24 Sept - 25 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
Slopeside Estate Guesthouse: Hot tub, AC, Grill
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, (4 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.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A covered porch with a grill, two Adirondack chairs, and a fire pit.

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

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (2 reviews)
"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...
United States
Devin
The price is €624
includes taxes & fees
20 Oct - 21 Oct
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
A bedroom with a bed, two bedside tables, and a nightstand.

17. 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 €325
includes taxes & fees
29 Sept - 30 Sept
4BR Home | Walk Downtown Rutland + Trails
A two-story wooden cabin with a balcony, illuminated windows, and a front door.

18. 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 €739
includes taxes & fees
24 Sept - 25 Sept
BearRight- AC, Pool, Hot Tub, Grill, FirePit
A cabin with a deck and a stone chimney.

19. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is €1,498
includes taxes & fees
24 Sept - 25 Sept
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A cozy living room with a stone fireplace, a sofa set, and a dining table.

20. 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 €732
includes taxes & fees
25 Sept - 26 Sept
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 10 hours ago
Woodstock Inn & Resort

Find out more about Chittenden

Chittenden Holiday Homes information

Number of reviews
134
Accommodation
660 Holiday Homes
Lowest Price
€176
Highest Price
€1,498