Woodstock Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Woodstock

Fridge, microwave, oven, stovetop
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more
9.0 out of 10, Wonderful, (12)
"Everything was perfect "
United States
jennifer
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more
Exterior
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
9.8 out of 10, Exceptional, (225)
"Cute house, convenient to exploring the Woodstock area. Had everything we needed. The house doesn't have central air but once we got the air conditioners turned on in each bedroom and the living room it was plenty cool. Host was very attentive and provided clear communication in advance. "
United States
Lisa R.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (52)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Indoor pool
Mountain Green
Mountain Green
2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
United States
Dennis
The price is HK$1,446
HK$1,939 total
includes taxes & fees
28 Oct - 29 Oct
Mountain Green
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (127)
"Terrific and comfortable place to stay! Amazing firepit!"
United States
Amy S.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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
9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$583
HK$1,968 total
includes taxes & fees
27 Oct - 28 Oct
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Exterior
Killington Retreat
Killington Retreat
2.0 star property
9.6 out of 10, Exceptional, (14)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
United States
shawn c.
Killington Retreat
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
8.0 out of 10, Very good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
United States
John Q.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
The price is HK$1,165
HK$1,497 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Property grounds
Winterplace at Okemo
Winterplace at Okemo
4.0 star property
8.8 out of 10, Excellent, (24)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo
Private kitchen
Solitude Village at Okemo
Solitude Village at Okemo
4.0 star property
8.0 out of 10, Very good, (31)
"Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also."
United States
Larry
Solitude Village at Okemo
Property grounds
Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (23)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
Canada
Victoria M.
The price is HK$1,166
HK$1,453 total
includes taxes & fees
2 Nov - 3 Nov
Treehouse at Wise Pines- SoBo
Exterior
Okemo Mountain Lodging
Okemo Mountain Lodging
3.5 star property
7.8 out of 10, Good, (28)
"I had an amazing time with my family, I will definitely be coming back "
United States
Yenifer
Okemo Mountain Lodging
Property grounds
Idyllic Lakefront House Suited Two Families
Idyllic Lakefront House Suited Two Families
9.6 out of 10, Exceptional, (171)
"We spent 11 nights at the house, everything was great."
United States
Brian C.
Idyllic Lakefront House Suited Two Families
Exterior
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
10.0 out of 10, Exceptional, (113)
"Clean and great location!"
United States
Alex P.
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (124)
"This place was quite simply brilliant. I stay with my wife and four kids. The kids range in age from 10-17 and we had a great stay exploring the Upper Valley area"
United Kingdom
Matthew C.
Beautifully renovated with fireplace and coffee bar
Interior
Killington Vermont Ski and Snowmobiling House
Killington Vermont Ski and Snowmobiling House
9.2 out of 10, Wonderful, (44)
"Spacious and nice location. The home met our needs. Basic home with some necessities lacking like soap, shampoo, washcloths, and paper towels. Coffee maker did not function well. Cooking utensils could use an upgrade. Needs a thorough cleaning and we noticed this right away upon arrival. Hot tub did not seem to work. No air conditioning, which should be clearly noted in the property description."
United States
Jon D.
Killington Vermont Ski and Snowmobiling House
Fridge, microwave, oven, stovetop
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
10.0 out of 10, Exceptional, (112)
"The house is beautiful. We had a great time! Plenty of space of everyone to spread out. Great fire pit for summer use and easy access to Okemo for skiing! The hosts were available to answer any questions and responded very quickly! We will definitely stay here again."
United States
Jill M.
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Living area
Killington Sapphire
Killington Sapphire
9.4 out of 10, Exceptional, (8)
"Everything we needed to enjoy your family trip!"
United States
Kristen B.
Killington Sapphire
Property grounds
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
9.4 out of 10, Exceptional, (21)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
United States
Dan G.
The price is HK$1,165
HK$2,846 total
includes taxes & fees
27 Oct - 28 Oct
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodstock Hotel Reviews

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"The hotel is wonderful! Beds are comfortable, water pressure and temp in the shower is SO good! And the continental breakfast is very good - plus the dining area is relaxing and enjoyable. Would HIGHLY recommend you checking this place out!"
Gretchen 1-night trip
Posted 4 days ago
Fireside Inn & Suites West 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Woodstock?

Expedia has 30 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 Green Mountain National Forest 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.