Woodstock Vacation Rentals

Vacation Rentals in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Idyllic Lakefront House Suited Two Families
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (142)
"Perfect family weekend ,! House clean & plenty of room for 5 adults & 1 child. Picture perfect, boating fishing, Crowley's cheese factory 10 minutes away. Definitely would love to return !"
The price is $234
$513 total
includes taxes & fees
22 Jun - 23 Jun
Idyllic Lakefront House Suited Two Families
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (58)
"Was just visiting Vermont to fish for the weekend so I didn’t need anything fancy but it was quite nice"
Beautifully renovated with fireplace and coffee bar
Lakefront home with amazing views, fireplace, firepit, & gas grill
Fridge, microwave, oven, stovetop
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Interior
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
8.0 out of 10, Very Good, (14)
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Killington Center Inn & Suites by Killington VR - Studios
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
The price is $106
$337 total
includes taxes & fees
4 Jun - 5 Jun
Killington Center Inn & Suites by Killington VR - Studios
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, (38)
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Treehouse at Wise Pines- SoBo
1 bedroom
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is $165
$203 total
includes taxes & fees
4 Jun - 5 Jun
Treehouse at Wise Pines- SoBo
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Aerial view
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, (7)
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The price is $138
$344 total
includes taxes & fees
4 Jun - 5 Jun
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Outdoor spa tub
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, (12)
"Nothing but positive things to say about the house. Would stay there again."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (107)
"Clean home close to downtown. Responsive owner. Highly recommended"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (28)
"Loved everything about it. Will look to book again"
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Don't see what you're looking for?
See all available properties in Woodstock
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.

Woodstock Vacation Rental Travel Info

Number of vacation rentals
5
Popular accommodation
Woodstock private vacation homes
Known landmarks
Suicide Six Ski Area, Woodstock Town Hall Theatre and Woodstock Country Club
International airports
Rutland, VT (RUT-Rutland Southern Vermont Regional) and Lebanon, NH (LEB-Lebanon Municipal)

Other types of properties in Woodstock you may be interested in

Woodstock Inn & Resort
Lobby
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (444)
"Lovely inn, always taking great care of visitors."
The price is $399
$479 total
includes taxes & fees
4 Jun - 5 Jun
Woodstock Inn & Resort
The Shire Woodstock
Property grounds
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (557)
"Fantastic "
The price is $183
$213 total
includes taxes & fees
4 Jun - 5 Jun
The Shire Woodstock
Sleep Woodstock Motel
Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (352)
"This is a very nice hotel, very clean, close to Woodstock town very good value. "
The price is $149
$164 total
includes taxes & fees
4 Jun - 5 Jun
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.

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as CNY768 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to Red Wagon Toy Company, or you can choose a more remote option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your vacation.

How many vacation rentals are there in Woodstock?

Expedia has 27 vacation 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 Mount Tom Peak are a couple of picturesque spots to enjoy the outdoors. While here, VINS Nature Center and Vermont Institute of Natural Science are other places worth a visit.

What’s a vacation rental in Woodstock like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Woodstock. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.

Recent reviews of Woodstock properties
Expedia 亿客行 verified reviews

The Shire Woodstock

The Shire Woodstock

5/5 Excellent
"Fantastic "
A verified traveler stayed at The Shire Woodstock
Posted 23 hours ago
The Shire Woodstock