Search Holiday Rentals in Woodstock

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Top Holiday Rentals in Woodstock

Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (57)
"This was a great stay. The condo was located in a quiet safe area in Quechee. Very clean, easy checkin process and it had all the amenities and fully stocked. The host was extremely responsive and easy to deal with. I would highly recommend staying here. Chris"
Beautifully renovated with fireplace and coffee bar
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. "
Killington Center Inn & Suites by Killington VR - Studios
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
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Fridge, microwave, oven, stovetop
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
10.0 out of 10, Exceptional, (16)
"From my first inquiry Dave had been responsive snd helpful. Beautiful house and we couldn’t ask for closer to Okemo trails. So much room in the home for all 17 of us. A fall trip back might be in our future for leave changing views."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Exterior
Charming 1 BR Mountain Green Resort Condo. Steps to the mountain! 3C8
10.0 out of 10, Exceptional, (12)
"I have stayed at a few units in this building and this one is among the nicest. The location of the building is great and the amenities are a nice touch!"
Charming 1 BR Mountain Green Resort Condo. Steps to the mountain! 3C8
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
1 bedroom, free WiFi, bed sheets
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 £151
per night
6 May - 7 May
Treehouse at Wise Pines- SoBo
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (173)
"Very clean and all accommodations Definitely good to go!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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 £232
per night
4 May - 5 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - 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, (156)
"Communication with owners was amazing. Heather was a great respondent and communicator. We were able to get three generations under one roof for a quiet and relaxing family getaway. We shared old stories around the fireplace and played cards late into the night (which is ten thirty pm, for us). Both my father and sister commented, at separate times, that the location was relaxing and peaceful. The pictures represent the property correctly. This was my first experience with VRBO and I am...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
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
Exterior
Amazing Mountain Condo - Right across the street to Killington Resort
9.8 out of 10, Exceptional, (165)
"Great location and very clean. You can walk to Snowshed or Ramshead Lodges. Nathan was great and very communicative. I would highly recommend."
Amazing Mountain Condo - Right across the street to Killington Resort
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
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
Indoor spa tub
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (12)
"Wonderful location located just south of the slopes. A bit of a walk to the lift but doable and fantastic trail to ski home. Very clean, loft area was a great addition. Very nice to have complimentary shampoo/conditioner/soap and dishwasher and laundry detergent. Everything we need for baking/meals. Lots of extra pillows!"
Trail Creek 33 | Condo in Killington
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (29)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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
Outdoor dining
Waterfront Cabin- look down on water from deck, private docks & fire pit
9.6 out of 10, Exceptional, (36)
"We enjoyed our time here!!! Beautiful view !"
Waterfront Cabin- look down on water from deck, private docks & fire pit
Fridge, microwave, oven, stovetop
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (27)
"this was a great house for us. there was space for everyone. the kitchen is very well stocked and the beds comfortable. it is a cozy house with rustic decor. the location is great. there are not enough wine glasses and the towels are small but those are minor details! we would go back, especially in another season to use the screen porch!"
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, (56)
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
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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 Holiday Rental Travel Info

Other types of properties in Woodstock you may be interested in

Deluxe Suite | Individually decorated, desk, blackout curtains, iron/ironing board
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (349)
"This was one of the cleanest room I have ever been in. Everything was spotless and very well appointed. Great room."
The price is £118
per night
5 May - 6 May
Sleep Woodstock Motel
Family Suite, 2 Bedrooms | Private kitchen | Microwave, coffee/tea maker, electric kettle
506 On the River Inn
4.0 star property
9.4 out of 10, Exceptional, (868)
"Quiet Beautiful Friendly Relax ing "
The price is £227
per night
5 May - 6 May
506 On the River Inn
Lobby
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (440)
"Beautiful hotel in a great location. Every member of the staff were friendly and accommodating. Highly recommend! "
The price is £282
per night
6 May - 7 May
Woodstock Inn & Resort
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 £151 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 26 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 Dana House Museum 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.

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