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Woodstock Holiday Rentals

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Our top choices for Woodstock holiday rentals

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is NZ$411
includes taxes & fees
10 July - 11 July
Mountain Green

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (11 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is NZ$353
includes taxes & fees
13 July - 14 July
Cozy Rutland Retreat

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (17 reviews)
"Was good"
United States
Ariel W.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (1 review)
"Great stay as always. "
United States
debbie r.
The price is NZ$307
includes taxes & fees
6 July - 7 July
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is NZ$588
includes taxes & fees
7 July - 8 July
Resort condo with mountain views, full kitchen, and free WiFi

Brookside Cabin - Your Vermont Offgrid Escape

Brookside Cabin - Your Vermont Offgrid Escape
Brookfield
The price is NZ$637
includes taxes & fees
7 July - 8 July
Brookside Cabin - Your Vermont Offgrid Escape

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is NZ$444
includes taxes & fees
19 July - 20 July
Addie's Place: A Quiet and Quirky Guesthouse

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

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
The price is NZ$463
includes taxes & fees
3 July - 4 July
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is NZ$427
includes taxes & fees
7 July - 8 July
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is NZ$826
includes taxes & fees
7 July - 8 July
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is NZ$899
includes taxes & fees
7 July - 8 July
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is NZ$760
includes taxes & fees
30 July - 31 July
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location, "
United States
Bryan R J.
The price is NZ$617
includes taxes & fees
20 July - 21 July
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is NZ$393
includes taxes & fees
9 July - 10 July
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Mendon
The price is NZ$851
includes taxes & fees
28 July - 29 July
Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is NZ$470
includes taxes & fees
7 July - 8 July
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Top-floor condo with mountain views & covered parking space

Top-floor condo with mountain views & covered parking space
Killington
9.0 out of 10, Wonderful, (31 reviews)
"Eceptional views, loved the covered parking, ammenities were clean."
United States
Mark A.
The price is NZ$645
includes taxes & fees
7 July - 8 July
Top-floor condo with mountain views & covered parking space

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
Efficient condo near slopes with kitchenette & great location
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, 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 NZ$411 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?

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This highly rated holiday home rental in Woodstock is located in a rural location, 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 games. Another good choice for your trip to Woodstock is Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town.

How many holiday rentals are there in Woodstock?

Expedia has 31 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 Ottaquechee River are a couple of picturesque spots to enjoy the outdoors. While here, Red Wagon Toy Company 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.