Woodstock Holiday Rentals

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Our top choices for Woodstock holiday rentals

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Amazing place! "
United States
Tara
The price is AU$775
includes taxes & fees
4 Apr - 5 Apr
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"Cleanness, quiet, and friendly "
United States
Zhongchun
The price is AU$271
includes taxes & fees
6 Apr - 7 Apr
Treehouse at Wise Pines- NoBo

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is AU$317
includes taxes & fees
26 Apr - 27 Apr
Addie's Place: A Quiet and Quirky Guesthouse

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AU$1,408
includes taxes & fees
5 Apr - 6 Apr
Cozy Vermont Cabin · Mountain Views · Near Okemo

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is AU$558
includes taxes & fees
4 Apr - 5 Apr
Killington condo 5 min to killington resort

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.
Killington
9.6 out of 10, Exceptional, (72 reviews)
"Amazing ski-in/out property slope-side! We enjoyed our stay very much! "
United States
Jason
The price is AU$1,589
includes taxes & fees
4 Apr - 5 Apr
Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (36 reviews)
"Great ski-in, ski-out property."
United States
Kristi C.
The price is AU$1,173
includes taxes & fees
4 Apr - 5 Apr
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful house! It had everything we needed for a fun and relaxing week. "
United States
Joshua
The price is AU$541
includes taxes & fees
4 Apr - 5 Apr
Killington Retreat | Deck-Fire Pit-Mountain Views!

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Okemo Village
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time , the location was amazing and the owner responded very quickly for any questions or concerns "
United States
Thomas B.
The price is AU$786
includes taxes & fees
5 Apr - 6 Apr
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AU$463
includes taxes & fees
8 Apr - 9 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is AU$443
includes taxes & fees
7 Apr - 8 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

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, (14 reviews)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
The price is AU$595
includes taxes & fees
6 Apr - 7 Apr
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (23 reviews)
"I enjoy the location "
United States
troy
The price is AU$338
includes taxes & fees
7 Apr - 8 Apr
Mountain Green

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is AU$426
includes taxes & fees
6 Apr - 7 Apr
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall

The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall
Killington
9.2 out of 10, Wonderful, (48 reviews)
"One of the best vrbo to date thank you!!!"
United States
jim c.
The price is AU$1,648
includes taxes & fees
6 Apr - 7 Apr
The Matterhorn House: Killington Chalet w/ Hot Tub, Views, Game Room - Ideal Spring to Fall

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is AU$1,772
includes taxes & fees
6 Apr - 7 Apr
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is AU$437
includes taxes & fees
7 Apr - 8 Apr
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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 AU$348
includes taxes & fees
5 Apr - 6 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Killington
10.0 out of 10, Exceptional, (82 reviews)
"It is a very cozy 1BR and we enjoy our stay very much!"
United States
Yongsheng X.
The price is AU$417
includes taxes & fees
6 Apr - 7 Apr
Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.

BruinsDen- Fooseball, Hot Tub, Mountain Views

BruinsDen- Fooseball, Hot Tub, Mountain Views
Killington
9.8 out of 10, Exceptional, (18 reviews)
"We loved our stay, felt like home away from home. A perfect place to relax after a day on the slopes. Grateful for our time there. #recommend!"
United States
Jennifer C.
The price is AU$1,819
includes taxes & fees
5 Apr - 6 Apr
BruinsDen- Fooseball, Hot Tub, Mountain Views
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 favourite 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 depend 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 AU$317 per night. Entering your travel dates in the search wizard might find you 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 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?

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock: This holiday home rental outside of Woodstock is located on a river, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.