Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

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

Woodstock
9.8 out of 10, Exceptional, (227)
"Lovely property. Peaceful and beautiful surroundings."
United States
Karen G.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Barnard
9.0 out of 10, Wonderful, (12)
"Great location and beautiful setting."
United States
Peter T.
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

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

Woodstock
10.0 out of 10, Exceptional, (59)
"So beautiful and peaceful"
United States
Andrea C.
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
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is €231
includes taxes & fees
30 Nov - 1 Dec
Mountain Green

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €224
includes taxes & fees
1 Dec - 2 Dec
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

2.5 star property
Rutland
The price is €168
includes taxes & fees
1 Dec - 2 Dec
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Killington Retreat

2.0 star property
Killington
9.8 out of 10, Exceptional, (17)
"It was clean and check-in was simple. "
United States
David M.
Killington Retreat

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington
8.4 out of 10, Very good, (38)
"Easy access to Killington Mountain "
United States
Dave S.
The price is €247
includes taxes & fees
30 Nov - 1 Dec
Cozy condo on ski shuttle route with free WiFi & full ktichen

The Cabin that brings people together

Bridgewater
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together

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

Cavendish
10.0 out of 10, Exceptional, (30)
"Beautiful property and excellent accommodations"
United States
Anthony W.
The price is €319
includes taxes & fees
2 Dec - 3 Dec
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Killington
9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
United States
Shawn C.
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

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

Killington
8.2 out of 10, Very good, (38)
"Room was constantly too hot. Otherwise a great stay"
United States
Cameron M.
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
9.8 out of 10, Exceptional, (60)
"Ski in/ Ski out Great locationJoel was very helpful and friendly. Really enjoyed our stay. "
United States
cynthia c.
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

killington
9.6 out of 10, Exceptional, (17)
"Great place to stay. Central location, bedrooms spacious and common areas w/plenty of space to hang out."
United States
Scott B.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mount Holly
9.8 out of 10, Exceptional, (226)
"It was our summer vacation with our family to Vermont and it happens to be our most favorite place to go! We loved the cabin. It was so cute and we enjoyed our stay! Vermont is a place to unwind and relax…..it’s our home away from home! "
United States
Kristen K.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is €165
includes taxes & fees
1 Dec - 2 Dec
Treehouse at Wise Pines- SoBo

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo
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

Find out more about Woodstock

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 €165 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. 

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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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This holiday home rental outside of Woodstock is located in the city centre, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Woodstock?

Expedia has 30 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, 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.