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Top Holiday Rentals in Woodstock

Our top choices for Woodstock holiday rentals

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (220)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (23)
"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is £191
includes taxes & fees
24 Aug - 25 Aug
Mountain Green

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (163)
"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

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is £157
includes taxes & fees
24 Aug - 25 Aug
Treehouse at Wise Pines- SoBo

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

9.0 out of 10, Wonderful, (54)
"There were dead bugs in the bathroom sink and bath, but it's fairly easy to clean them. Everything else in the room is great!"
The price is £130
includes taxes & fees
25 Aug - 26 Aug
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (11)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (21)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

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

9.8 out of 10, Exceptional, (175)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is £252
includes taxes & fees
8 Sept - 9 Sept
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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

3.0 star property
9.6 out of 10, Exceptional, (12)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (114)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar

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

8.0 out of 10, Very good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (140)
"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Vineyard Cabin

10.0 out of 10, Exceptional, (1)
"The cabin was quaint and perfect for what we were looking for. We were close to town, but felt way more isolated. The cabin was off grid, but had running water and electricity. We were comfortable and very happy with our stay. It was beautiful and wildlife was abundant. The hosts were attentive, but not intrusive. We will definitely be back."
Vineyard Cabin

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (60)
"Small and cozy"
Custom-built Tiny House on forested lot near Quechee
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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Top Woodstock Hotel Reviews

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, 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 36 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. While here, VINS Nature Center and Saskadena Six Ski Area 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.