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

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

9.2 out of 10, Wonderful, (11)
"Everything was perfect "
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

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 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 NZ$485
includes taxes & fees
24 Feb - 25 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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 NZ$322
includes taxes & fees
2 Mar - 3 Mar
Efficient condo near slopes with kitchenette & great location

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

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

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is NZ$719
includes taxes & fees
23 Feb - 24 Feb
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

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

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (94)
"Nice place. we had a great time. "
Beautifully renovated with fireplace and coffee bar

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

9.0 out of 10, Wonderful, (45)
"Great simple, easy to get to. Close to the mountain! Everything was clean and well set up. As other reviewers have noted, its not recently updated (although furniture is all newer and very nice/comfortable) but not needed. Great for a couple or small family for an easy convenient stay near the mountain. I would highly recommend it and would likely come again!"
The price is NZ$337
includes taxes & fees
16 Mar - 17 Mar
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

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

8.4 out of 10, Very good, (15)
"Beautiful ski condo, very conveniently located, super clean with a very comfy bed! Had a great stay."
The price is NZ$624
includes taxes & fees
23 Feb - 24 Feb
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (169)
"Great house for family. Enjoyed our trip. So close to Okemo. "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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 NZ$324
includes taxes & fees
5 Mar - 6 Mar
Treehouse at Wise Pines- SoBo

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

Ski-in/ski-out condo with mountain view, private balcony, & fireplace

7.4 out of 10, Good, (3)
"Fun trip and great stay at this condo. Family of 3 easily fit comfortably and enjoyed the proximity to the base lodge lifts."
Ski-in/ski-out condo with mountain view, private balcony, & fireplace

Well-appointed studio right downtown - less than a mile to Okemo Mountain

9.2 out of 10, Wonderful, (11)
"Easy check in clean place "
The price is NZ$446
includes taxes & fees
27 Feb - 28 Feb
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

9.6 out of 10, Exceptional, (48)
"Everything was great with this rental. Easy to get to, convenient location, plenty of space, and instructions were clear. Nice living room with a smart TV in case you have to stay inside."
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (22)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

9.8 out of 10, Exceptional, (165)
"Great central location for Okemo skiing. Okemo was super busy so MOOver was perfect and super easy and convenient for getting to/from mountain! Walkable to some great restaurants. Apartment had everything you need for your home away from home but DON’T FORGET TO BRING LINENS! "
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
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 resort, beautiful property-only issue was room was cold - aside from that, loved the stay "
The price is NZ$649
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (727)
"We spend a weekend at the shire every winter and absolutely love it! It’s walkable to the heart of Woodstock, close to Killington, and even allows us to bring our dog! Can’t wait for next year!"
The price is NZ$293
includes taxes & fees
25 Feb - 26 Feb
The Shire Woodstock

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (964)
"It’s been our second time going to On the River Inn VT and we’ve been amazed both times we went there! The view of the lake/courtyard is beautiful and the hotel in general is very clean. My daughter loved the pool and the game room. The staff were very helpful with everything we asked for and the breakfast was top notch. Definitely worth the trip!"
The price is NZ$399
includes taxes & fees
23 Feb - 24 Feb
506 On the River Inn
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?

Idyllic Lakefront House Suited Two Families: 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 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. 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.