Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (90)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House

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

Carriage House - 280 Private Acres; Views, Gardens, Skiing, Farm, Serenity

10.0 out of 10, Exceptional, (52)
"Perfect! The home was clean and comfortable for our group of four. Plenty of outdoor activities nearby. Woodstock has lovely shops and restaurants. We will be back."
Carriage House - 280 Private Acres; Views, Gardens, Skiing, Farm, Serenity

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is NZ$467
includes taxes & fees
7 Apr - 8 Apr
Mountain Green

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

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (203)
"Very clean. Well equipped. Close to the ski slope."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

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

8.4 out of 10, Very good, (29)
" Convenient location right off Killington Rd. Short drive to ski or restaurants. One bar/restaurant on site- Vermont Craft. Newly renovated studio, clean on arrival. Check-in as described, did not need to contact host during stay. Thorough details provided in pre arrival communications. "
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (25)
"Very friendly costumer service, we arrived late and we're greated with kindness. "
Solitude Village at Okemo

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (99)
"Our stay was terrific! Such a lovely renovated home! "
Beautifully renovated with fireplace and coffee bar

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

9.8 out of 10, Exceptional, (21)
"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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$456
includes taxes & fees
7 Apr - 8 Apr
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

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

9.0 out of 10, Wonderful, (70)
"Unit is comfortable, clean and very accessible to the Clock tower base of Okemo mtn for skiing. That's why you choose this unit. It definitely can use some updates and general maintenance. Items homeowner could address:Shower drainage issues, several lightbulbs need changing, add some cutlery (There should be enough spoons to cover the amount of people the unit can accomodate), Update lockbox and the door lock on ski closet. "
The price is NZ$460
includes taxes & fees
7 Apr - 8 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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$317
includes taxes & fees
1 Apr - 2 Apr
Treehouse at Wise Pines- SoBo

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

9.8 out of 10, Exceptional, (205)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"Overall great stay for the family and friends. Communication was easy and available as needed. One issue that arose with people in the studio was handled expeditiously by Dave. Great location and layout for kids and adults to have separate areas. Would highly recommend "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (37)
"Really awesome hot tub. The Jets were the strongest Jets I’ve ever felt. I loved it. It’s about a four or five minute walk in ski boots to get to the trail.House was adequately stocked for cooking. I do always bring my own pans and knives.They need to restock the forks apparently everybody must’ve thrown them in the garbage. Overall, great house I’d recommend it for families with kids."
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.2 out of 10, Wonderful, (75)
"We were a mixed group, one family of 4 and two additional adults. So we had private bedrooms for all. The house was a mix of rustic charm and some newer house elements. We were just there one night, so did not spend a whole lot of time at the house, but it was a perfect fit for our needs. Thanks Bethany!"
The price is NZ$545
includes taxes & fees
31 Mar - 1 Apr
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.8 out of 10, Exceptional, (6)
"Everything was excellent. 3 baths 3 beds. Perfect. Bring coffee filters and hangers."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (29)
"House is in a beautiful setting with incredible views from all the front rooms. Kitchen is well outfitted and beds are comfortable. Listing is accurate."
The price is NZ$799
includes taxes & fees
1 Apr - 2 Apr
Spacious country home, beautiful sunsets, 40 acres

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (157)
"This was our third trip back to this house, so needless to say we enjoy staying set the property. It has enough rooms and beds to fit us and our extended family comfortably, has everything we want and need (multiple bathrooms, a fil kitchen,) plus there's the bonus of a working fireplace. The location can't be beat. Right on the lake, about 7 minutes from the Jackson Gore base area, and Erin walking distance to the dust house. We love it. "
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, (504)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is NZ$650
includes taxes & fees
6 Apr - 7 Apr
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (733)
"Clean, nice, great value, nice place"
The price is NZ$283
includes taxes & fees
7 Apr - 8 Apr
The Shire Woodstock

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (982)
"The hotel has a lot of extras that enhance the stay for everyone. Very thoughtfully done and already planning another trip back."
The price is NZ$407
includes taxes & fees
30 Mar - 31 Mar
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?

Beautifully renovated with fireplace and coffee bar: This holiday home rental outside of Woodstock is located on a river, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Expedia has 37 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 Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Green Mountain National Forest 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.