Woodstock Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Woodstock holiday rentals

Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse
Hartford
10.0 out of 10, Exceptional, (5 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is NZ$333
includes taxes & fees
22 Feb - 23 Feb
Addie's Place: A Quiet and Quirky Private Guesthouse

Fall Line Condos by Killington VR - Studios

Fall Line Condos by Killington VR - Studios
2.0 star property
Killington
7.0 out of 10, Good, (2 reviews)
"Yes by a shuttle very easy"
United States
Philip
The price is NZ$895
includes taxes & fees
17 Feb - 18 Feb
Fall Line Condos by Killington VR - Studios

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is NZ$344
includes taxes & fees
11 Mar - 12 Mar
Vermont Suite | 10 Min to Killington & Woodstock

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.0 out of 10, Good, (46 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is NZ$448
includes taxes & fees
11 Mar - 12 Mar
Clean & bright condo with mountain views & modern kitchen - walk to lifts

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$462
includes taxes & fees
8 Mar - 9 Mar
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.6 out of 10, Exceptional, (5 reviews)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
The price is NZ$343
includes taxes & fees
17 Feb - 18 Feb
Cozy Rutland Retreat

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is NZ$610
includes taxes & fees
4 Mar - 5 Mar
Jack S`Bearo - Slopes, Fireplace, Pool.

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (20 reviews)
"Great !"
United States
Raul
The price is NZ$458
includes taxes & fees
11 Mar - 12 Mar
Mountain Green

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.2 out of 10, Wonderful, (13 reviews)
"Great property, as advertised."
United States
Chris A.
The price is NZ$539
includes taxes & fees
10 Mar - 11 Mar
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

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
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is NZ$547
includes taxes & fees
11 Mar - 12 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Killington
10.0 out of 10, Exceptional, (24 reviews)
"Really enjoyed our time there. It's a simple and straightforward apartment. Easy to get to, and a really nice location."
United States
Matthew G.
The price is NZ$591
includes taxes & fees
4 Mar - 5 Mar
CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
Rutland
9.4 out of 10, Exceptional, (10 reviews)
The price is NZ$315
includes taxes & fees
16 Mar - 17 Mar
Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (20 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
The price is NZ$969
includes taxes & fees
16 Feb - 17 Feb
Charming Lakefront Cottage on Lake Mascoma

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, (7 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is NZ$475
includes taxes & fees
5 Mar - 6 Mar
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.6 out of 10, Exceptional, (67 reviews)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is NZ$550
includes taxes & fees
22 Feb - 23 Feb
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

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

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very good, (38 reviews)
"Great place. Met our needs. "
United States
Sean K.
The price is NZ$490
includes taxes & fees
11 Mar - 12 Mar
Cozy condo on ski shuttle route with free WiFi & full ktichen

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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is NZ$567
includes taxes & fees
10 Mar - 11 Mar
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (23 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is NZ$473
includes taxes & fees
8 Mar - 9 Mar
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is NZ$450
includes taxes & fees
16 Mar - 17 Mar
Efficient condo near slopes with kitchenette & great location

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is NZ$502
includes taxes & fees
25 Feb - 26 Feb
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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$315 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 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?

Idyllic Lakefront House Suited Two Families: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Woodstock?

Expedia has 29 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 Lakota Lake and Green Mountain National Forest 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.