Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

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
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
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!!
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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
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
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
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is €487
includes taxes & fees
22 Jun - 23 Jun
Idyllic Lakefront House Suited Two Families
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 €192
includes taxes & fees
29 May - 30 May
Treehouse at Wise Pines- SoBo
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
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
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 €310
includes taxes & fees
29 May - 30 May
Killington Center Inn & Suites by Killington VR - Studios
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is €270
includes taxes & fees
29 May - 30 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
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
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
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
Outdoor spa tub
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, (11)
"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
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!
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
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 €326
includes taxes & fees
29 May - 30 May
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Outdoor dining
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
"This house was everything we needed. Ample space for a large group. Tom and Carla were very responsive. Our group had a terrific experience!"
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
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.

Other types of properties in Woodstock you may be interested in

Lobby
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (442)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."
The price is €411
includes taxes & fees
2 Jun - 3 Jun
Woodstock Inn & Resort
Property grounds
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (555)
"While the location is convenient, because of its walkable distance to the town center, restaurants and shops, it also has the dreamiest riverbank in the back. We absolutely loved our access to the fire pits by the river in the evening. Our room was spotless, spacious with a comfortable bed. We’ll definitely be returning again. "
The price is €196
includes taxes & fees
4 Jun - 5 Jun
The Shire Woodstock
Deluxe Suite
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (352)
"This was one of the cleanest room I have ever been in. Everything was spotless and very well appointed. Great room."
The price is €151
includes taxes & fees
29 May - 30 May
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodstock holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as €192 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 holiday.

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 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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: 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 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Woodstock?

Expedia has 27 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 Mount Tom Peak are a couple of picturesque spots to enjoy the outdoors. While here, Red Wagon Toy Company 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.

Recent reviews of Woodstock properties
Expedia verified reviews

Align Inn Vermont

Align Inn Vermont

5/5 Excellent
"Very nice hotel right by Quechee Gorge. Good breakfast choices. I took a nice walk down the gorge in the morning. "
A verified traveller stayed at Align Inn Vermont
Posted 2 days ago
Align Inn Vermont