A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Woodstock holiday rentals

A deck with outdoor furniture, a flag, and a view of a forested hill.

1. Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway

Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Woodstock
The price is HK$2,471
HK$4,086 total
includes taxes & fees
22 Sept - 23 Sept
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

2. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is HK$1,843
HK$2,436 total
includes taxes & fees
24 Sept - 25 Sept
Fat Sheep Farm & Cabins
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

3. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is HK$612
HK$1,826 total
includes taxes & fees
20 Sept - 21 Sept
Mountain Green
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

4. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is HK$404
HK$1,821 total
includes taxes & fees
20 Sept - 21 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A living room with a fireplace, a sofa, a coffee table, and a television.

5. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$733
HK$2,979 total
includes taxes & fees
20 Sept - 21 Sept
Resort condo with mountain views, full kitchen, and free WiFi
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

6. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is HK$437
HK$2,315 total
includes taxes & fees
30 Sept - 1 Oct
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

7. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (1 review)
"Lovely cabin, as described. Very clean and comfortable. Our only comments, which are not criticisms, but suggestions are: 1). Post the wifi password. We only got the password in an older communication and, fortunately one of us had that open on an older message and could see it. Otherwise, there was no cell service and we were unable to find it. 2) Leave some towels in the bathroom instead of all in the front linen closet. Thanks for a great stay."
United States
Peter C.
The price is HK$2,330
HK$6,994 total
includes taxes & fees
21 Sept - 22 Sept
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A sunroom with wicker furniture, large windows, and string lights.

8. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (18 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$1,020
HK$1,826 total
includes taxes & fees
21 Sept - 22 Sept
Addie's Place: A Quiet and Quirky Guesthouse
A person standing on a sandy beach by a river with trees in the background.

9. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
The price is HK$2,189
HK$4,087 total
includes taxes & fees
20 Sept - 21 Sept
Cabin on the hill Ascutney Vt - 4 bedrooms

10. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is HK$1,288
HK$3,143 total
includes taxes & fees
12 Oct - 13 Oct
The Suites at Killington Center
A large house with a fire pit and outdoor seating.

11. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is HK$2,322
HK$5,043 total
includes taxes & fees
27 Sept - 28 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
A two-story house with a green roof, a covered porch, and a driveway with a parked car.

12. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is HK$941
HK$1,810 total
includes taxes & fees
23 Sept - 24 Sept
Bridgewater Living - Ski VT Suite
A cabin with a deck and a stone chimney.

13. 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$2,716
HK$8,610 total
includes taxes & fees
21 Sept - 22 Sept
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A view of a grassy area with a ski lift and a building in the background.

14. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Property is on 4th floor almost at the end, so you have to walk the most with heavy bags..that was pain.. had problems with heating and cooling system. Also requested for 1 hour late check out at the time of booking, never received any response on top cleaning stuffs were sent to the property sharp at 10 am. Our friends rented another property on the same building and they could easily checked out late at 12:00 pm. Otherwise we enjoyed our stay and proximity to the slope is unparallel."
United States
Indrajit A.
The price is HK$593
HK$2,002 total
includes taxes & fees
14 Oct - 15 Oct
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A golf course with a winding path, trees, and a distant mountain range.

15. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is HK$783
HK$1,819 total
includes taxes & fees
18 Sept - 19 Sept
Efficient condo near slopes with kitchenette & great location
A two-story house with a porch, a staircase, and a front door.

16. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is HK$783
HK$1,872 total
includes taxes & fees
18 Sept - 19 Sept
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A two-story house with a porch, a staircase, and a front door.

17. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is HK$824
HK$2,129 total
includes taxes & fees
18 Sept - 19 Sept
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

18. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (54 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is HK$1,687
HK$3,331 total
includes taxes & fees
21 Sept - 22 Sept
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A residential area with multiple houses, a sign for 'FALL LINE', and a well-maintained lawn.

19. Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Killington
8.0 out of 10, Very good, (6 reviews)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
The price is HK$699
HK$1,956 total
includes taxes & fees
20 Sept - 21 Sept
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
A spacious restaurant with high ceilings, exposed ductwork, and a mix of wooden and metal furniture.

20. Killington resort: Walk to Mountain, Bike, Pool

Killington resort: Walk to Mountain, Bike, Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is HK$875
HK$2,744 total
includes taxes & fees
22 Sept - 23 Sept
Killington resort: Walk to Mountain, Bike, Pool
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 Woodstock Hotel Reviews

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"To be clear, this isn't a five-star hotel, but it was an excellent stay--the property was clean, quiet, and pretty new. The bed was comfortable, wifi was stable, and HVAC worked just fine. I didn't try most of the amenities so can't answer to that. If I had any negatives, one of the elevators was down during my three-day stay. And the location isn't ideal if you're looking to be near something walkable. Totally recommend for a clean and quiet stay."
David 2-night trip
Posted 1 hour ago
Hilton Garden Inn Hanover Lebanon

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

Look no further and take a look at our great range of rental properties in Woodstock!

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your holiday.

What are some of the best holiday rentals that Woodstock has to offer?

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated holiday home rental in Woodstock is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind. Other favourite homes for rent in Woodstock are Classic, cozy farmhouse in the 4 season playground of VT's prettiest town! and Scenic Ridge Cabin with Sweeping Vermont Views.

How many holiday rentals are there in Woodstock?

Expedia has 35 holiday rentals for your stay in Woodstock.

What’s there to see and do in Woodstock?

Cultural attractions include Woodstock Town Hall Theatre and Billings Farm and Museum, whereas Marsh-Billings-Rockefeller National Historical Park and Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Green Mountain National Forest are other places worth a visit.

What’s a holiday rental in Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.