Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (64)
"This was a perfect spot for two to stay. Close walk to town and quick drive to Okemo. Had everything you would need to cook simple meals also."
The price is AU$497
includes taxes & fees
10 Mar - 11 Mar
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"David was a great host. Place was as described, clean, conveniently located on Okemo mountain, walk right up to sachem trail, stay towards the left at the bottom and the quad bubble lift is right there."
Ski In/Out Studio at Okemo on Sachem Trail

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (42)
"My fiancé and I stayed here over Christmas break for 4 nights. Snowboarded on Killington for 3 of those days. We were in close proximity to not only the mountain, but the shops to get our boards waxed and restaurants/bars. Those restaurants/bars were essential as this rental unit only has a microwave and mini fridge (as advertised). But for a place to just kick back and relax, clean up, and sleep. It was in a prime location. The spa services were available to us and while we didn't get to use...
The price is AU$291
includes taxes & fees
18 Feb - 19 Feb
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (92)
"We had a great winter weekend! The accommodations were just what we needed, perfect location and the coffee bar was amazing! We cant wait to come back again!"
Beautifully renovated with fireplace and coffee bar

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy Mountain Condo with Ski-In/Ski-Out Access, and Electric Fireplace

Cozy Mountain Condo with Ski-In/Ski-Out Access, and Electric Fireplace

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (201)
"Beautiful cozy cottage, but the road is a little loud. The creek and backyard are gorgeous."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (22)
"This place was great, Communication with the Killington Rental Associates was wonderful. The house was as it photographs. It was a perfect spot to ring in the New Year. After skiing, the hot tub and Sauna were a welcome retreat for the weary skiing crowd, the Kitchen was well stocked with just about anything you could need to prepare meals for a large crowd. The Bar was an added highlight for apre-Ski. There was enough space for a large crowd to gather in one spot, and enough spots to...
Spectacular opportunity to enjoy the finest property in Killington Summit

Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

9.4 out of 10, Exceptional, (35)
"Apartment was exactly as described. Great place to relax when not skiing. Property manager was prompt in responding to questions."
Killington Condo Penthouse Mountain View Underground parking Pool Hot Tub - 3F10

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (91)
"Great location in town and close to shuttle. Able to walk to restaurants. Host very responsive and answered quickly. Comfortable beds. Great for 5 adults. Easily fit 3 cars in driveway."
The price is AU$793
includes taxes & fees
4 Mar - 5 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The place is everything it describes, however I missed the part where the bathrooms are in a separate building and they are shared. Thankfully for us there was nobody else staying there. Everything was very clean. Other than that I was satisfied. "
The price is AU$299
includes taxes & fees
10 Feb - 11 Feb
Treehouse at Wise Pines- SoBo

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

9.2 out of 10, Wonderful, (66)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is AU$505
includes taxes & fees
10 Feb - 11 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

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

8.4 out of 10, Very good, (27)
"Very nice property. Clean and well appointed."
The price is AU$564
includes taxes & fees
12 Feb - 13 Feb
Comfortable mountain gem with pool, mountain views, & indoor parking space

Efficient condo near slopes with kitchenette & great location

9.2 out of 10, Wonderful, (27)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is AU$364
includes taxes & fees
13 Feb - 14 Feb
Efficient condo near slopes with kitchenette & great location

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.8 out of 10, Excellent, (14)
"The property was exactly as advertised and clean. The pool was open and it was a good option to relax. The acces to parking was terrible - muddy, sandy, icy gravel. It is clear that nobody was thinking about this at all. The access to lifts was not ski in/out, but shuttle was great, and running all time! There was a ski locker, which was convenient, though nobody told us about it and we figured it out ourselves. Card for pool did not work but the office was open and provided the correct one,...
The price is AU$663
includes taxes & fees
10 Feb - 11 Feb
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families
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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Other types of properties in Woodstock you may be interested in

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (501)
"Great trip! "
The price is AU$594
includes taxes & fees
9 Mar - 10 Mar
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (722)
"Super clean and they were extremely accommodating being we got in really late!!! "
The price is AU$290
includes taxes & fees
10 Feb - 11 Feb
The Shire Woodstock

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (456)
"The suite was lovely and spacious. Perfect for a family trip away"
The price is AU$179
includes taxes & fees
10 Feb - 11 Feb
Sleep Woodstock Motel
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.

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Red Wagon Toy Company, 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?

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge: This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 29 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. Other popular places to visit in the area include Killington Resort and Okemo Mountain Resort.

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.