Woodstock holiday homes

We found 1,089 holiday rentals — enter your dates for availability
Discover a selection of 34 homes and other holiday rentals in Woodstock that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as air conditioning and a pool. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Woodstock

Showing deals for:20 Nov - 27 Nov

Imagine having mountain trail views while playing bartender!
Welcome to the Highline Lodge!
The great room features your own private bar, gas fireplace, and cozy seating!
Mix up some drinks for your party at the 9 seat bar with 65" smart TV!
Exceptional
(67 reviews)

Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!

Killington

8% off
NZ$28,036
for 7 nights, 1 room
NZ$4,005 per night
includes taxes & fees
Rent An Entire Inn! Sleeps 30! As seen on Staycation TV!
Interior
Pool
Outdoor dining
Property grounds
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
NZ$52,284
for 7 nights, 1 home
NZ$7,469 per night
includes taxes & fees
Reading Farms Estate
Carrara marble counters, breakfast bar and eat in table
living room with fireplace and gorgeous custom details
pond is river fed and very clear water
Room
Exceptional
(122 reviews)

Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!

Bridgewater Corners

12% off
NZ$14,375
for 7 nights, 1 home
NZ$2,054 per night
includes taxes & fees
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
Outdoor spa tub
Small views of all 3 living room spaces and wet bar
Exterior
Private kitchen
Exceptional
(67 reviews)

Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail

Bridgewater Corners

13% off
NZ$14,795
for 7 nights, 1 home
NZ$2,114 per night
includes taxes & fees
Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
Property grounds
Living area
Living area
Private kitchen
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
NZ$12,783
for 7 nights, 1 cabin
NZ$1,826 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
Wide windows bring daylight into the shared living and dining space.
The pass-through counter keeps the kitchen connected to the living room.
From the dining table, the adjoining living room is open and easy to reach.
Sit down for coffee beside the window, with the front door and living room nearby.
Exceptional
(18 reviews)

Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.

Killington

8% off
NZ$19,486
for 7 nights, 1 cabin
NZ$2,784 per night
includes taxes & fees
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
The sauna building!  Just steps from the back door. St your spa experience await
Deck dining above the brook!
spiral stairs lead up to master bedroom suite or down to den & laundry
Lofted master suite with views to the night sky from the king bed
Exceptional
(75 reviews)

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

Woodstock

9% off
NZ$4,309
for 7 nights, 1 chalet
NZ$616 per night
includes taxes & fees
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Private kitchen
Living area
Room
Living area
Exceptional
(6 reviews)

Luxury 5-bedroom house in Quechee near golf and Quechee Club

White River Junction

12% off
NZ$13,669
for 7 nights, 1 home
NZ$1,953 per night
includes taxes & fees
Luxury 5-bedroom house in Quechee near golf and Quechee Club
Den area main level (baby not included!)
Master bedroom looking Southwest (upper level
Winter looking Southeast
Kitchen (main level)
Exceptional
(25 reviews)

All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Mount Holly

8% off
NZ$6,721
for 7 nights, 1 cabin
NZ$960 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
Snowy woods frame the deck hot tub on cold winter days.
Pass plates and drinks through the counter opening without missing what is happening in the living room.
Wood railings and carpeted steps carry the cabin's warm finish into the stairway.
Meals and conversation flow easily between the dining table and the adjoining living room.
Exceptional
(65 reviews)

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington

7% off
NZ$8,482
for 7 nights, 1 cabin
NZ$1,212 per night
includes taxes & fees
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Enjoy the outdoor hot tub available late fall to early spring.
Dining
Welcome to our Quechee Home!
Living area
Exceptional
(33 reviews)

6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont

White River Junction

8% off
NZ$11,170
for 7 nights, 1 home
NZ$1,596 per night
includes taxes & fees
6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont
Living area
Exterior
Terrace/patio
Interior
Wonderful
(5 reviews)

Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit

Ludlow

6% off
NZ$15,355
for 7 nights, 1 home
NZ$2,194 per night
includes taxes & fees
Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit
Outdoor dining
IMG 1540
Main dining space with seating for 12
Coffee options galore!
Exceptional
(7 reviews)

Stylish new A Frame with Lake Rescue dock access

Ludlow

8% off
NZ$8,379
for 7 nights, 1 home
NZ$1,197 per night
includes taxes & fees
Stylish new A Frame with Lake Rescue dock access
House from Outside
Living room and dining area with views of Ascutney Mountain
View from the deck
Kitchen  with soapstone counters, cherry wood floors, and walk-in food closet.
Exceptional
(42 reviews)

Exquisite Log Home with views near Woodstock, Vermont

Brownsville

15% off
NZ$5,344
for 7 nights, 1 home
NZ$763 per night
includes taxes & fees
Exquisite Log Home with views near Woodstock, Vermont
Stretch out on the leather sectional with daylight coming through windows on two sides.
There is space for the group around the central stone fireplace beneath the cabin's exposed timber ceiling.
Cook, serve, and sit down together across an open space centered on the dining table.
Settle into the sectional while the stone fireplace anchors the open main room.
Exceptional
(21 reviews)

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

7% off
NZ$5,166
for 7 nights, 1 cabin
NZ$738 per night
includes taxes & fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Living area
Interior
Private kitchen
Terrace/patio
Exceptional
(9 reviews)

5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated

Killington

8% off
NZ$11,508
for 7 nights, 1 home
NZ$1,644 per night
includes taxes & fees
5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated
Dining area
Chef's Kitchen
Front of House - Summer
Front of house in winter
Exceptional
(60 reviews)

Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!

Plymouth

13% off
NZ$13,720
for 7 nights, 1 home
NZ$1,960 per night
includes taxes & fees
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
Fitness facility
Pool
Interior
Views from one of several decks in the unit
Exceptional
(56 reviews)

Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section

Killington

8% off
NZ$13,578
for 7 nights, 1 home
NZ$1,940 per night
includes taxes & fees
Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section
Room
Interior
Living area
Interior
Exceptional
(105 reviews)

Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub

Killington

8% off
NZ$7,870
for 7 nights, 1 home
NZ$1,124 per night
includes taxes & fees
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
Stairs to the living area
Exterior
Sofa bed
Main house garden
Exceptional
(115 reviews)

Woodstock Village Carriage House

Woodstock

8% off
NZ$3,841
for 7 nights, 1 cottage
NZ$549 per night
includes taxes & fees
Woodstock Village Carriage House
Fireplace from Living area couch
Indoor Pool & Hot tub at Sport center
Ski out path just outside of Condo which is the bottom corner unit
View of Condo and Bear Mtn from parking lot in fall. Note woodshed on left.
Exceptional
(111 reviews)

Ski-on Ski-Off Killington 2 BR Condo at Sunrise, with Pool, Hot Tub and Gym

Killington

8% off
NZ$3,507
for 7 nights, 1 apartment
NZ$501 per night
includes taxes & fees
Ski-on Ski-Off Killington 2 BR Condo at Sunrise, with Pool, Hot Tub and Gym
Exterior
Main deck
Entrance
Dinning Area
Exceptional
(29 reviews)

Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.

Ludlow

8% off
NZ$8,434
for 7 nights, 1 home
NZ$1,205 per night
includes taxes & fees
Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.
view from the Foundry
Living room
Interior
Exterior detail
Exceptional
(61 reviews)

Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

Killington

8% off
NZ$13,188
for 7 nights, 1 home
NZ$1,884 per night
includes taxes & fees
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding
Terrace/patio
Pool
Private kitchen
Dining
Exceptional
(9 reviews)

Soothing family-friendly townhome in Quechee Lakes

Quechee

7% off
NZ$3,168
for 7 nights, 1 home
NZ$453 per night
includes taxes & fees
Soothing family-friendly townhome in Quechee Lakes
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Woodstock

  • Picturesque Village Centre: Enjoy the quaint charm of Woodstock’s historic village, perfect for leisurely strolls and local culture immersion.
  • Outdoor Adventures: From skiing in winter to nature trails in summer, outdoor enthusiasts will find plenty to explore.
  • Rich History: Discover the town’s heritage through its historic homes and landmarks.
  • Family-Friendly Atmosphere: Woodstock offers a welcoming vibe, ideal for families seeking a relaxing yet adventurous break.
  • Stunning Landscapes: Appreciate the breathtaking natural beauty and scenic views that define this charming Vermont destination.

Top attractions in and around Woodstock

Woodstock, Vermont, is a charming destination perfect for outdoor enthusiasts and families alike. With opportunities for skiing and adventure, visitors can explore stunning national parks, historic homes, and breathtaking canyons. The town's rich culture and picturesque landscapes offer a unique experience, making it an ideal spot for those seeking both relaxation and adventure. Discover the delightful attractions that make Woodstock a memorable holiday destination.

  • Mount Tom Peak: Experience adventure and breathtaking scenery atop Mount Tom Peak, nestled within Woodstock’s vibrant outdoors.
  • Billings Farm and Museum: Immerse yourself in local culture at Billings Farm and Museum, a living history site celebrating Woodstock’s agricultural heritage.
  • Quechee Gorge Bridge: Discover outdoor thrills and stunning views at Quechee Gorge Bridge, only 10km from Woodstock, perfect for a scenic day trip.

Things to do recommended for couples

Woodstock offers a charming escape for couples. Enjoy a scenic walk along the Ottauquechee River, explore the quaint shops in the village, or unwind with a couples' massage at a local spa. Don't forget to savour a romantic dinner at a cosy restaurant featuring farm-to-table cuisine.

Things to do recommended for families

Families visiting Woodstock can explore the picturesque Marsh-Billings-Rockefeller National Historical Park, where children can enjoy nature trails and learn about conservation. The Billings Farm & Museum offers interactive experiences with farm animals and historical exhibits, making it a fun and educational day out for all ages.

Things to do recommended for groups

Groups visiting Woodstock can enjoy the local charm by exploring quaint shops, indulging in artisanal foods, and experiencing scenic nature walks in the picturesque countryside.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Woodstock

When travelling with a group, family, pets, or planning an extended stay, it's important to filter your options based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Woodstock with a group: Consider how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for group get-togethers. Luckily, you can use filters on Vrbo to find all of these and more.
  • Traveling to Woodstock with young kids: Journeying with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you'll want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many, a family holiday simply isn’t complete without their furry companion by their side. If that describes you, take a look at Vrbo properties that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of holiday rentals offering deals for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Woodstock

Woodstock, Vermont offers a charming holiday experience with its rich historical vibe and family-friendly atmosphere. Explore its scenic village centre, enjoy outdoor adventures in warmer months, and immerse yourself in the local culture. Whether you’re skiing in winter or enjoying nature trails in summer, Woodstock provides a perfect blend of history and adventure for every traveller.

  • Hanover: Located a mere 21km from Woodstock, Hanover is a vibrant city known for its rich cultural atmosphere and stunning outdoor adventures. Home to a historic college university, the city offers a unique blend of educational experiences and scenic landscapes. Visitors can enjoy activities such as hiking in the nearby mountains, exploring the serene lakes, or taking part in winter sports at local ski fields. Hanover's charming downtown is filled with quaint shops and delightful eateries, making it a perfect spot for a leisurely stroll or a cultural immersion.
  • Quechee: Just 8km from Woodstock, Quechee is renowned for its breathtaking natural beauty and outdoor pursuits. This charming city is a haven for adventure seekers, featuring excellent ski resorts and ski fields that attract winter sports enthusiasts. In addition to skiing, visitors can explore the stunning Quechee Gorge, often referred to as the Grand Canyon of Vermont. The picturesque lake nearby provides opportunities for kayaking and relaxing picnics, while the local historic college university adds to the area's educational charm.
  • White River Junction: Located 16km from Woodstock, White River Junction is a dynamic city offering a perfect blend of adventure and outdoor activities. Renowned for its ski fields and resorts, this city is ideal for winter sports lovers. Visitors can also explore the surrounding landscapes, which include charming lakes and the striking canyon gorge. The area's historic college university enriches the cultural scene, making it a great place to enjoy artistic events and local cuisine. With its easy access to outdoor recreation, White River Junction is a must-visit for those seeking adventure.

Best time to go to Woodstock

If you're planning a trip to Woodstock, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January19.6°F (-6.9°C)Light RainMostly CloudyAverage
February21.6°F (-5.8°C)Light RainMostly CloudySlightly Low
March29.7°F (-1.3°C)Light RainMostly CloudySlightly Low
April42.1°F (5.6°C)Light RainMostly CloudySlightly Low
May55.2°F (12.9°C)Light RainMostly SunnyAverage
June62.8°F (17.1°C)Light RainMostly SunnyAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly High
August66.9°F (19.4°C)Light RainMostly SunnyAverage
September59.7°F (15.4°C)Light RainMostly SunnySlightly High
October48.0°F (8.9°C)Light RainMostly CloudySlightly High
November35.4°F (1.9°C)Light RainMostly SunnyAverage
December26.8°F (-2.9°C)Light RainMostly CloudyAverage

Booking with Vrbo is a breeze

Are you keen to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. You might also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect accommodation for your adventure.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated space where you can start planning new adventures, pick up where you left off, or review and organise your bookings. Your saved or reserved properties are neatly arranged into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The historical city of Woodstock awaits you

Enjoy the area's architecture, history and museums with a rental holiday home in Woodstock. Renowned for its riverfront, restaurants and shopping, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Woodstock

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that makes Woodstock a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Saskadena Six Ski Area (3 mi / 4.9 km)
  • Sugarbush Farm (3.8 mi / 6.1 km)
  • Quechee State Park (5.5 mi / 8.8 km)
  • Upper Valley Aquatic Center (8.8 mi / 14.2 km)
  • Killington Golf Course (13.8 mi / 22.2 km)
  • Killington Resort (13.9 mi / 22.3 km)

Exploring the natural features in Woodstock

Whether you're an adventurous traveller or just want to take in the scenery, Woodstock is a great place to spend some time outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Marsh-Billings-Rockefeller National Historical Park (1.3 mi / 2 km)
  • Quechee Gorge Bridge (5.6 mi / 9 km)
  • Silver Lake State Park (8.9 mi / 14.3 km)
  • Mount Ascutney (12.9 mi / 20.7 km)
  • Echo Lake (13.8 mi / 22.2 km)
  • Lake Rescue (15.1 mi / 24.2 km)

How to get to and around Woodstock

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.5 mi (16.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Springfield, VT (VSF-Hartness State), which is 19.4 mi (31.3 km) away.

Frequently asked questions

What is the best area to stay in Woodstock when booking a holiday home?
If you're thinking of a getaway to Woodstock, West Woodstock is one of the most desirable neighbourhoods to stay. Whether you're looking for a cottage, condo or another property type, you'll always have the entire place to yourself.
What is the most popular type of holiday home accommodation in Woodstock?
Based on our data, houses are the most in-demand holiday property type in Woodstock. But of course, everyone's idea of an awesome trip can vary. Bookabach has holiday homes of all sizes and shapes, and we'll help you locate the perfect fit.
How much does it cost to rent a holiday home in Woodstock?
Different things can affect the price of a holiday home in Woodstock, such as the time of year, property type and length of stay. Still, all Bookabach homes have something in common — unbeatable value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Woodstock?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Woodstock travel dates to view your available options on Bookabach. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday homes in Woodstock?
Pack a tug toy and treats for the pooch in your life because Woodstock has 13 stays that roll out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Woodstock?
Add another level of fun to your adventure by booking one of the three houses with a private pool in Woodstock. Use our search filter to find the kind of property you want on Bookabach, and then spend leisurely days playing and splashing in a swimming pool that's for your exclusive use.
What are popular home amenities in Woodstock?
When it comes to home amenities that people are looking for in Woodstock, mountain views, a garden and a water view rank highest. With Bookabach holiday homes, there are choices to match your style and taste, whether you're going on a trip with your partner, your family or even pets.
Are there large group holiday homes in Woodstock?
Take your pick of seven Bookabach holiday properties in Woodstock that can sleep five or more people. You'll get all the privacy and space you need to hang out with your loved ones — and nobody else.
Are there holiday homes in Woodstock that welcome kids?
Woodstock has 13 family-friendly holiday homes to pick from. And finding a stay that welcomes children is a breeze with Bookabach's "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get conveniences and perks such as bunk beds, private pools and yards.
What are the top attractions for families in Woodstock?
There are plenty of awesome things to do and see with the family in Woodstock, such as:
  • Mount Tom Peak
  • Lakota Lake
  • Union Arena Community Centre
Are there one-bedroom holiday homes in Woodstock?
You can choose from four one-bedroom homes in Woodstock. Whether you're searching for a comfy cottage or a cabin, Bookabach's one-bedroom homes are great if you don't need huge amounts of space. One of the main perks of having your own pad? You'll never need to share your trip with strangers.
Are there holiday homes with WiFi in Woodstock?
Take your pick of five holiday homes with WiFi in Woodstock. If you want to disconnect from the world during your break, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Woodstock?
Woodstock has seven holiday homes where you can relax and recharge in air-conditioned comfort. To locate a property on Bookabach that offers this perk, choose your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Woodstock?
Age restrictions can differ between properties on Bookabach, so check the rules of the holiday home in Woodstock you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Woodstock for?
The amount of time you can book a Woodstock holiday home for is down to the property. Just enter your dates of travel to view options that offer extended stays. They feature everything you need to make your extended trip more enjoyable and comfortable, such as kitchens and laundries. Some Bookabach holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.

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