Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Woodstock holiday rentals

Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (10 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$1,042
HK$1,850 total
includes taxes & fees
26 May - 27 May
Addie's Place: A Quiet and Quirky Guesthouse
Property grounds

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
9.0 out of 10, Wonderful, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$588
HK$2,023 total
includes taxes & fees
7 May - 8 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is HK$1,234
HK$2,268 total
includes taxes & fees
4 May - 5 May
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is HK$415
HK$2,299 total
includes taxes & fees
5 May - 6 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,042
HK$2,325 total
includes taxes & fees
7 May - 8 May
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

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$384
HK$1,746 total
includes taxes & fees
3 May - 4 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Property grounds

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very good, (36 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is HK$494
HK$2,185 total
includes taxes & fees
3 May - 4 May
Comfortable mountain gem with pool, mountain views, & indoor parking space
Private kitchen

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$776
HK$1,895 total
includes taxes & fees
10 May - 11 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is HK$627
HK$1,526 total
includes taxes & fees
3 May - 4 May
Vermont Double Queen Suite | 10 Mins to Killington
Exterior

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.0 out of 10, Wonderful, (15 reviews)
"The apartment was very comfortable, including a very convenient bathroom. There was everything we needed. Though the apartment did not look like the photo on the internet site. There was no street number on the building which made it difficult to find it. "
United States
lilya l.
The price is HK$627
HK$1,956 total
includes taxes & fees
3 May - 4 May
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is HK$599
HK$1,470 total
includes taxes & fees
10 May - 11 May
Cozy Rutland Retreat
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is HK$881
HK$2,385 total
includes taxes & fees
3 May - 4 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Indoor pool

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.0 out of 10, Good, (48 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is HK$462
HK$1,860 total
includes taxes & fees
8 May - 9 May
Clean & bright condo with mountain views & modern kitchen - walk to lifts
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is HK$979
HK$3,266 total
includes taxes & fees
8 May - 9 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Indoor pool

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, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$580
HK$2,729 total
includes taxes & fees
3 May - 4 May
Resort condo with mountain views, full kitchen, and free WiFi
Living area

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is HK$698
HK$2,417 total
includes taxes & fees
3 May - 4 May
Killington condo 5 min to killington resort
Indoor pool

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (32 reviews)
"Great location."
United States
Dustin S.
The price is HK$627
HK$2,290 total
includes taxes & fees
3 May - 4 May
Welcoming condo near the slopes with free WiFi and full kitchen
Exterior

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is HK$744
HK$1,918 total
includes taxes & fees
5 May - 6 May
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
TV, fireplace, books

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very good, (39 reviews)
"Great place. Met our needs. "
United States
Sean K.
The price is HK$580
HK$2,042 total
includes taxes & fees
3 May - 4 May
Cozy condo on ski shuttle route with free WiFi & full ktichen
Exterior

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$783
HK$1,975 total
includes taxes & fees
3 May - 4 May
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
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

Best Western West Lebanon-Hanover Hotel

Best Western West Lebanon-Hanover Hotel

10/10 Excellent
"Staff and property was Excellent. But EXPEDIA totally messed up the reservation. Their offshore help was friendly but very unhelpful. Their unwillingness to resolve their screw-up cost be $$$ (and I am just a low paid worker), so it made the caused the entire stay to be miserable"
Mark 1-night trip
Posted 16 hours ago
Best Western West Lebanon-Hanover Hotel

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.

How many holiday rentals are there in Woodstock?

Expedia has 31 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 Ottaquechee River are a couple of picturesque spots to enjoy the outdoors. While here, VINS Nature Center and Saskadena Six Ski Area 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.