Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

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."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We had a great time-- the apartment was clean and cute and the linens fresh. "
The price is €263
includes taxes & fees
16 Apr - 17 Apr
Mountain Green

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (204)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (100)
"We had a wonderful stay at Wanda and Eran's condo in Quechee. The home was beautiful, very clean, and looks just like the photos. The kitchen is well stocked with dishes, pots and pans and spices/cooking oils. Wanda was extremely helpful with restaurant suggestions, local activities and was very responsive."
Beautifully renovated with fireplace and coffee bar

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

9.8 out of 10, Exceptional, (206)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

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

9.2 out of 10, Wonderful, (27)
"Perfect location for a ski trip to Okemo! Very close to the mountain and shops in town. Hot tub was great!"
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, (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

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 €168
includes taxes & fees
22 Apr - 23 Apr
Treehouse at Wise Pines- SoBo

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

8.6 out of 10, Excellent, (17)
"Thanks for everything "
The price is €328
includes taxes & fees
9 Apr - 10 Apr
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

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

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (30)
"The view from the front rooms and porch of the house are breathtaking throughout the day and evening. The kitchen is well stocked. It feels private and remote but is 15 minutes from groceries and hardware and good restaurants. The listing is exactly as promised."
Spacious country home, beautiful sunsets, 40 acres

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 €246
includes taxes & fees
9 Apr - 10 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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, (7)
"The location of this unit was ideal for people who like to vacation without having to drive. We literally skied to The Sunrise Cafe for dinner the first night. All of our outdoor adventures started right from our door with excellent access to trails. The Community center had a great hot tub and free equipment to use. We would definitely go back. "
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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, (38)
"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

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

10.0 out of 10, Exceptional, (106)
"Great house. Great location. Clean and well stocked house "
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Charming Lakefront Cottage on Lake Mascoma

10.0 out of 10, Exceptional, (5)
"Beautiful location, easy to get to. Gorgeous main floor with open floor plan and loads of nice design touches. Bedrooms are great. There's a nice little space adjacent to the LR with childrens books, games and toys, which kept our 18 month grandson busy. We skiied Mt Sunapee only 30 min away. highly recommend "
The price is €476
includes taxes & fees
6 Apr - 7 Apr
Charming Lakefront Cottage on Lake Mascoma

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

8.6 out of 10, Excellent, (28)
"I would recommend to friends and family "
The price is €250
includes taxes & fees
8 Apr - 9 Apr
Comfortable mountain gem with pool, mountain views, & indoor parking space

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 €296
includes taxes & fees
6 Apr - 7 Apr
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
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, (507)
"All the staff, whether the bartender, wait staff, men at the front door, desk clerk everyone greeting my wife and I with a smile and were very helpful."
The price is €337
includes taxes & fees
6 Apr - 7 Apr
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (734)
"Great stay!"
The price is €131
includes taxes & fees
10 Apr - 11 Apr
The Shire Woodstock

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (986)
"Beautiful pool setting"
The price is €229
includes taxes & fees
8 Apr - 9 Apr
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.