Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (15)
"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
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Beautiful Myrtle Beach Condo with Amenities Galore
8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
9.0 out of 10, Wonderful, (18)
"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, (39)
"Accurate representation of the property. Check in was easy after some confusion as the access door is right next to another unit and not wanting to interfere with another group late at night. Owners were able to clarify and said they would put a better note into the welcome message to alleviate future confusion. Overall, good price and would stay again."
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (20)
"The location of the property was great.. Centrally located to everything we wanted to see. I would have liked to have a vacuum or even a broom available. The place had a few areas that could have been cleaner. "
Trail Creek 33 | Condo in Killington
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (19)
"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"
The price is NZ$303
includes taxes & fees
24 Nov - 25 Nov
Treehouse at Wise Pines- SoBo
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
8.2 out of 10, Very good, (33)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (113)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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$754
includes taxes & fees
23 Nov - 24 Nov
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
8.4 out of 10, Very good, (25)
"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (36)
"This property was just what we were looking for in a weekend getaway in VT. Would highly recommend. "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (153)
"Our stay was wonderful, and the hosts were more than accomadating! Lovely home and very convenient to Ludlow and Okemo. "
Idyllic Lakefront House Suited Two Families
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
9.2 out of 10, Wonderful, (19)
"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
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, (483)
"Lovely hotel. Could do with some updates in areas but a very unique picturesque place . "
The price is NZ$637
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (682)
"The room was surprisingly clean and modern and the view out the back door towards the river and the hills across the river was awesome. The location was great: it was a short walk to downtown. All good. "
The price is NZ$352
includes taxes & fees
26 Nov - 27 Nov
The Shire Woodstock
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (422)
"friendly staff"
The price is NZ$205
includes taxes & fees
24 Nov - 25 Nov
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.
Beautiful view of the beach with palm trees

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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?

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Expedia has 28 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 Green Mountain National Forest and Marsh-Billings-Rockefeller National Historical Park are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and VINS Nature Center 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.