Woodstock Holiday Rentals

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Check prices for these dates

Tonight
31 Oct - 1 Nov
Tomorrow
1 Nov - 2 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Woodstock

Interior
A charming 1820's farmhouse
A charming 1820's farmhouse
10.0 out of 10, Exceptional, (29)
"Excellent accommodations! One of the best VRBO’s I’ve ever stayed in. There were 5 women traveling together for a long weekend and Carmen’s place was just the ticket with our own bedrooms and en suite bathrooms. We had the entire place to ourselves and felt very spoiled."
United States
kelly f.
The price is HK$7,025
HK$11,267 total
includes taxes & fees
2 Nov - 3 Nov
A charming 1820's farmhouse
Property grounds
Off Grid Glamping Shed with River Access
Off Grid Glamping Shed with River Access
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$455
HK$727 total
includes taxes & fees
4 Nov - 5 Nov
Off Grid Glamping Shed with River Access
Interior
Addie's Place: A Quiet and Quirky Private Guesthouse
Addie's Place: A Quiet and Quirky Private Guesthouse
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
The price is HK$932
HK$1,703 total
includes taxes & fees
19 Nov - 20 Nov
Addie's Place: A Quiet and Quirky Private Guesthouse
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington
Luxury Condo Tucked in the Heart of Killington
8.0 out of 10, Very good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is HK$923
HK$2,541 total
includes taxes & fees
1 Nov - 2 Nov
Luxury Condo Tucked in the Heart of Killington
Terrace/patio
Killington condo 5 min to killington resort
Killington condo 5 min to killington resort
9.4 out of 10, Exceptional, (8)
"Great little getaway! Loved the fireplace! Super warm and cozy, had everything we needed. "
United States
Erin F.
The price is HK$1,189
HK$3,011 total
includes taxes & fees
10 Nov - 11 Nov
Killington condo 5 min to killington resort
Fridge, microwave, oven, stovetop
The Carol - 10 minutes to Okemo & Newly Renovated
The Carol - 10 minutes to Okemo & Newly Renovated
10.0 out of 10, Exceptional, (6)
"Perfect place for a weekend ski trip to Okemo. The host was very helpful!"
United States
Thomas G.
The price is HK$1,224
HK$2,302 total
includes taxes & fees
6 Nov - 7 Nov
The Carol - 10 minutes to Okemo & Newly Renovated
Property grounds
Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is HK$1,165
HK$1,453 total
includes taxes & fees
6 Nov - 7 Nov
Treehouse at Wise Pines- SoBo
Smart TV, fireplace
Jack S`Bearo - Slopes, Fireplace, Pool.
Jack S`Bearo - Slopes, Fireplace, Pool.
10.0 out of 10, Exceptional, (11)
"Great location for pico and Killington mountain. Cute little condo with a very comfy master bed!"
United States
Summer F.
The price is HK$629
HK$2,116 total
includes taxes & fees
3 Nov - 4 Nov
Jack S`Bearo - Slopes, Fireplace, Pool.
Fridge, microwave, oven, stovetop
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
9.8 out of 10, Exceptional, (73)
"Wonderful, cozy, and comfy (bed is amazing) place to stay. Also very convenient location. Hosts clearly place directions and helpful tips around. Everything was a breeze! "
United States
Vanessa
The price is HK$614
HK$1,782 total
includes taxes & fees
4 Nov - 5 Nov
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Fridge, microwave, oven, stovetop
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
10.0 out of 10, Exceptional, (21)
"Excellent location "
United States
Colin G.
The price is HK$1,042
HK$2,354 total
includes taxes & fees
12 Nov - 13 Nov
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.
Property grounds
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!
10.0 out of 10, Exceptional, (2)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is HK$975
HK$2,224 total
includes taxes & fees
4 Nov - 5 Nov
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
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
4 Nov - 5 Nov
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
2.0 star property
10.0 out of 10, Exceptional, (9)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
United States
Nicholas M.
The price is HK$1,368
HK$2,402 total
includes taxes & fees
4 Nov - 5 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Ben & Jerry Suite | Minutes to Woodstock | Hiking
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is HK$575
HK$1,445 total
includes taxes & fees
17 Nov - 18 Nov
Ben & Jerry Suite | Minutes to Woodstock | Hiking
Exterior
Spacious country home, beautiful sunsets, 40 acres
Spacious country home, beautiful sunsets, 40 acres
9.8 out of 10, Exceptional, (42)
"The accommodations were great with plenty of room. We all wanted to lay on the living room couches because they were so comfortable! The property was nice and peaceful with lots of flowers, bushes and trees to observe."
United States
Karen P.
The price is HK$816
HK$3,490 total
includes taxes & fees
3 Nov - 4 Nov
Spacious country home, beautiful sunsets, 40 acres
Smart TV, fireplace
Wade`s World Ski Home FirePlace Shuttle location
Wade`s World Ski Home FirePlace Shuttle location
2.0 star property
9.6 out of 10, Exceptional, (5)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
The price is HK$680
HK$2,674 total
includes taxes & fees
4 Nov - 5 Nov
Wade`s World Ski Home FirePlace Shuttle location
Fridge, microwave, oven, stovetop
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
2.0 star property
9.8 out of 10, Exceptional, (11)
"Nice time, great location"
United States
Matthew K.
The price is HK$1,085
HK$3,365 total
includes taxes & fees
2 Nov - 3 Nov
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Fridge, microwave, dishwasher, coffee/tea maker
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
9.4 out of 10, Exceptional, (63)
"Great location and nicely appointed. Bus pickup to slopes was super easy"
United States
Robert
The price is HK$692
HK$1,888 total
includes taxes & fees
9 Nov - 10 Nov
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is HK$1,145
HK$3,774 total
includes taxes & fees
2 Nov - 3 Nov
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Golf
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Well-appointed studio right downtown - less than a mile to Okemo Mountain
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is HK$591
HK$1,931 total
includes taxes & fees
3 Nov - 4 Nov
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"very nice"
Brad 2-night trip
Posted 3 days ago
Jackson Gore Village

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?

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more: This highly rated holiday home rental in Woodstock is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.