A mountainous landscape with autumn-colored trees and rocky outcrops.

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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 Wallingford holiday homes

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.

1. 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 HK$872
HK$3,040 total
includes taxes & fees
6 Sept - 7 Sept
Killington Retreat | Deck-Fire Pit-Mountain Views!

2. 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 HK$713
HK$1,464 total
includes taxes & fees
29 Sept - 30 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.

3. 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 HK$727
HK$1,849 total
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

4. 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 HK$1,058
HK$3,846 total
includes taxes & fees
31 Aug - 1 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

5. 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 HK$1,383
HK$3,760 total
includes taxes & fees
6 Sept - 7 Sept
large ski ranch hot tub close to killington pets ok

6. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is HK$622
HK$2,146 total
includes taxes & fees
31 Aug - 1 Sept
Luxury Condo Tucked in the Heart of Killington
A deck with outdoor furniture, a table, and a view of a forested hillside.

7. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (20 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is HK$1,505
HK$4,188 total
includes taxes & fees
17 Sept - 18 Sept
Modern Farm House…minutes to Okemo; 2 King beds!
A two-story house with a covered porch and a garage.

8. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is HK$1,948
HK$6,920 total
includes taxes & fees
1 Sept - 2 Sept
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
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 HK$988
HK$2,135 total
includes taxes & fees
2 Sept - 3 Sept
CozyDen - AC, Grill, Bike to Mountain, Porch!
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

10. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
2.0 star property
Killington
The price is HK$1,568
HK$3,863 total
includes taxes & fees
2 Sept - 3 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

11. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking
Rutland
The price is HK$2,940
HK$5,769 total
includes taxes & fees
1 Sept - 2 Sept
Relaxing Rutland Retreat Near Skiing, Dining & Hiking
A covered porch with wooden flooring and a railing, featuring outdoor seating and a view of a bridge and greenery.

12. Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Perfect location. Neat place. Very clean!"
United States
Frank F.
The price is HK$1,270
HK$3,942 total
includes taxes & fees
31 Aug - 1 Sept
Okemo's Back Room - in the heart of the village on the shuttle route!
A two-story house with a covered porch and a gabled roof.

13. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.0 out of 10, Wonderful, (34 reviews)
"Very nice house to stay in Fair Haven VT. Worked perfectly for us and beautiful area. Clean and has everything you need."
United States
Amy G.
The price is HK$1,568
HK$3,039 total
includes taxes & fees
20 Sept - 21 Sept
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

14. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is HK$1,748
HK$5,564 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

15. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$1,665
HK$5,697 total
includes taxes & fees
31 Aug - 1 Sept
Breakaway House by Killington Vacation Rentals
A cabin with a deck and a stone chimney.

16. 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 HK$2,771
HK$8,653 total
includes taxes & fees
31 Aug - 1 Sept
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

17. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered 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 HK$1,540
HK$5,035 total
includes taxes & fees
31 Aug - 1 Sept
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

18. 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 HK$1,549
HK$5,040 total
includes taxes & fees
31 Aug - 1 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

19. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is HK$584
HK$2,034 total
includes taxes & fees
31 Aug - 1 Sept
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

20. 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 HK$1,474
HK$3,071 total
includes taxes & fees
1 Sept - 2 Sept
4BR Home | Walk Downtown Rutland + Trails
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 Wallingford Hotel Reviews

Lake Bomoseen Lodge

Lake Bomoseen Lodge

10/10 Excellent
"The view was gorgeous and the rental home was perfect for few adults along with few kids. Would visit again! The lodge tap room was a delight each night and the boating rental and free boat access was enjoyed by all. We loved the access to sit in Adirondack chairs along the lake any time of day or night"
Raska 4-night trip
Posted 6 hours ago
Lake Bomoseen Lodge

Find out more about Wallingford

Wallingford Vacation Homes information

Number of reviews
215
Accommodation
1074 Vacation Homes
Lowest Price
HK$1,464
Highest Price
HK$8,653

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