South Woodstock holiday rentals

We found 900 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in South Woodstock that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a pool. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – South Woodstock

Showing deals for:18 Dec - 25 Dec

Living area
Living area
Private kitchen
Property grounds
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
AU$16,306
for 7 nights, 1 cabin
AU$2,329 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
Carrara marble counters, breakfast bar and eat in table
living room with fireplace and gorgeous custom details
Room
Property grounds
Exceptional
(125 reviews)

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

Bridgewater Corners

12% off
AU$11,013
for 7 nights, 1 home
AU$1,573 per night
includes taxes & fees
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
lots of room to relax in front of fireplace
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
AU$11,286
for 7 nights, 1 home
AU$1,612 per night
includes taxes & fees
Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section
Indoor Pool at the Quechee Club
Dining
Enjoy the outdoor hot tub available late fall to early spring.
Welcome to our Quechee Home!
Exceptional
(33 reviews)

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

White River Junction

8% off
AU$8,815
for 7 nights, 1 home
AU$1,259 per night
includes taxes & fees
6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont
Exterior
Interior
Room
Interior
Exceptional
(105 reviews)

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

Killington

8% off
AU$10,379
for 7 nights, 1 home
AU$1,483 per night
includes taxes & fees
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
Interior
Small views of all 3 living room spaces and wet bar
Private kitchen
Outdoor spa tub
Exceptional
(67 reviews)

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

Bridgewater Corners

13% off
AU$19,948
for 7 nights, 1 home
AU$2,850 per night
includes taxes & fees
Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
Outdoor dining
Pool
Property grounds
Interior
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
AU$42,706
for 7 nights, 1 home
AU$6,101 per night
includes taxes & fees
Reading Farms Estate
Terrace/patio
Exterior
Private kitchen
Living area
Wonderful
(5 reviews)

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

Ludlow

6% off
AU$12,661
for 7 nights, 1 home
AU$1,809 per night
includes taxes & fees
Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit
Covered outdoor patio with views of the lake, connecting to king bedroom
Front of home (late fall sunset)
View (summer) from the covered / screened-in outdoor patio
The Great Room and dining table - seats 10
Exceptional
(20 reviews)

5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C

Ludlow

8% off
AU$15,295
for 7 nights, 1 home
AU$2,185 per night
includes taxes & fees
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
Fully stocked kitchen with breakfast nook and island
IMG 1540
Coffee options galore!
Outdoor dining
Exceptional
(7 reviews)

Stylish new A Frame with Lake Rescue dock access

Ludlow

8% off
AU$7,755
for 7 nights, 1 home
AU$1,108 per night
includes taxes & fees
Stylish new A Frame with Lake Rescue dock access
Lower Level Bar/Kitchenette
Image from trailhead
Living Room - looking out over mountains
Bedroom 3 - queen bed
Exceptional
(67 reviews)

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

Killington

8% off
AU$14,619
for 7 nights, 1 home
AU$2,088 per night
includes taxes & fees
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
House from Outside
Living room and dining area with views of Ascutney Mountain
Kitchen with soapstone counters, cherry wood floors, and walk-in food closet.
Second master with ensuite bathroom
Exceptional
(42 reviews)

Exquisite Log Home with views near Woodstock, Vermont

Brownsville

15% off
AU$4,332
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
Exquisite Log Home with views near Woodstock, Vermont
Front of house in winter
Chef's Kitchen
Yoga Studio
Dining area
Exceptional
(60 reviews)

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

Plymouth

14% off
AU$14,928
for 7 nights, 1 home
AU$2,133 per night
includes taxes & fees
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
Dining
Interior
Living area
Private kitchen
Exceptional
(9 reviews)

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

Killington

8% off
AU$12,782
for 7 nights, 1 home
AU$1,826 per night
includes taxes & fees
5 Min to Lodges & Town; Arcade & Ping Pong Table; Hot Tub; Renovated
Bedroom #2
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
AU$6,862
for 7 nights, 1 home
AU$980 per night
includes taxes & fees
Lake Front home on Lake Rescue. Sunset views, peaceful home with a private dock.
Outdoor pool in summer months
beautiful arial view of Sunrise in the fall
work out room at Sunrise
open floor plan condo with tons of amenities
Exceptional
(49 reviews)

True ski in/out condo at The Lodges - Trailside Luxury w/ pool & hot tub access

Killington

8% off
AU$12,688
for 7 nights, 1 apartment
AU$1,813 per night
includes taxes & fees
True ski in/out condo at The Lodges - Trailside Luxury w/ pool & hot tub access
Sun room, facing the lake
(amazing) Photo by guest
Photo by guest
Porch/Bar overlooking the lake
Exceptional
(119 reviews)

Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8

Ludlow

8% off
AU$4,397
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8
Main room facing north.
Terrace/patio
The Shepherds' Cabin
Main room facing northwest
Exceptional
(107 reviews)

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow

12% off
AU$3,743
for 7 nights, 1 cabin
AU$535 per night
includes taxes & fees
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
This closet provides plenty of room for coats and ski equipment.
Side of building
Living room with a new queen sleeper--view of Tribou Park
Bar with five stools for additional seating
Exceptional
(71 reviews)

Charming and Chic Village Rental

Woodstock

7% off
AU$3,683
for 7 nights, 1 apartment
AU$526 per night
includes taxes & fees
Charming and Chic Village Rental
Dining
Private kitchen
Exterior
Exterior detail
Exceptional
(101 reviews)

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

Mount Holly

8% off
AU$2,971
for 7 nights, 1 cabin
AU$424 per night
includes taxes & fees
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Living area
Living area
Pool
Exterior
Exceptional
(30 reviews)

3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside

Killington

8% off
AU$11,276
for 7 nights, 1 apartment
AU$1,611 per night
includes taxes & fees
3 Bed 3 Bath Luxury Ski-In/Ski-out Condo Killington Sunrise Village Slopeside
Interior
Outdoor dining
Exterior
Private kitchen
Exceptional
(83 reviews)

As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.

Ludlow

8% off
AU$5,679
for 7 nights, 1 home
AU$811 per night
includes taxes & fees
As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.
Interior
View from living room
Lake view
Interior
Exceptional
(187 reviews)

Idyllic Lakefront House Suited Two Families

Ludlow

8% off
AU$3,344
for 7 nights, 1 home
AU$478 per night
includes taxes & fees
Idyllic Lakefront House Suited Two Families
Living/Dining room with gas stove
Deck with chiminea
Stairs to the 2nd floor
Living room, antique wardrobe with TV and stereo
Exceptional
(85 reviews)

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor

8% off
AU$2,212
for 7 nights, 1 cottage
AU$316 per night
includes taxes & fees
Cozy Historic Hilltop Cottage with Mount Ascutney View

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Travel to friendly South Woodstock

Learn about the unique charm of South Woodstock with a stay in a holiday home rental. Travellers especially like the bars, restaurants and horse riding in this welcoming and romantic city. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around South Woodstock

Are you hoping to find attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that South Woodstock has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Saskadena Six Ski Area (6.8 mi / 10.9 km)
  • Sugarbush Farm (7.6 mi / 12.2 km)
  • Quechee Ski Hill (7.8 mi / 12.5 km)
  • Quechee State Park (7.9 mi / 12.7 km)
  • Upper Valley Aquatic Center (10.8 mi / 17.4 km)
  • Fox Run Golf Course (13.4 mi / 21.5 km)

Exploring the natural landscape of South Woodstock

Whether you're an adventurous traveller or just want to appreciate the scenery, South Woodstock is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Marsh-Billings-Rockefeller National Historical Park (4.7 mi / 7.6 km)
  • Quechee Gorge Bridge (7.9 mi / 12.8 km)
  • Mount Ascutney (9.3 mi / 14.9 km)
  • Echo Lake (10.5 mi / 17 km)
  • Lake Rescue (11.6 mi / 18.7 km)
  • Silver Lake State Park (12.2 mi / 19.7 km)

Transport options to and around South Woodstock

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 11.9 mi (19.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Springfield, VT (VSF-Hartness State), which is 15.4 mi (24.8 km) away.

Frequently asked questions

What is the best area to stay in South Woodstock when booking a holiday rental?
When considering a holiday rental in South Woodstock, Vermont, the area surrounding the picturesque village centre is often regarded as the best choice. This charming neighbourhood not only provides easy access to local amenities but also boasts stunning natural beauty. One of the top attractions nearby is the Marsh-Billings-Rockefeller National Historical Park, which offers delightful trails and insights into conservation history. Additionally, the Billings Farm & Museum provides a fantastic opportunity to learn about Vermont's rural heritage and enjoy interactive exhibits.In terms of accommodation options, South Woodstock features a variety of properties that cater to different preferences and budgets. Many of these rentals are set in serene locations, allowing guests to fully appreciate the tranquil Vermont landscape.
Where are the best South Woodstock ski resort rentals?
For the best ski resort rentals near South Woodstock, travellers should consider the picturesque village itself and the surrounding areas, particularly closer to the Okemo Mountain Resort, which is just a short drive away. In South Woodstock, visitors can find charming holiday homes and cosy cabins that often feature amenities like wood-burning stoves, spacious living areas, and fully equipped kitchens, making them great for families or groups after a day on the slopes.Properties in this area frequently come with outdoor spaces, such as decks or patios, allowing guests to enjoy the serene views of the Vermont countryside. Many rentals also offer easy access to local trails for cross-country skiing or snowshoeing, enhancing the winter experience.Additionally, the nearby town of Woodstock is known for its quaint New England atmosphere and offers a variety of lodging options, including converted barns and historic inns that provide a unique stay. These accommodations often include amenities like complimentary breakfast, hot tubs, and communal areas for relaxation. The region is also rich in local dining and shopping options, ensuring that guests can enjoy the charm of Vermont both on and off the slopes.
What is the most popular type of holiday rental accomodation in South Woodstock?
In South Woodstock, holiday houses are the predominant type of holiday rental, with several available throughout the area. These homes typically provide spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and inviting living areas for relaxation after a day of exploring the scenic Vermont countryside. Many of these properties also offer outdoor spaces, such as decks or gardens, where guests can enjoy the tranquil surroundings.
Are there any family house rentals in South Woodstock?
In South Woodstock, Vermont, there are several family-friendly house rentals available, making it an excellent destination for those travelling with children. The area is known for its picturesque countryside and proximity to outdoor activities, including hiking and skiing. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy nature.Visitors can explore nearby attractions such as the Marsh-Billings-Rockefeller National Historical Park, which provides beautiful trails and educational opportunities about the local environment. Additionally, the charming village centre, with its quaint shops and restaurants, is just a short drive away, superb for family outings.
Can I rent a holiday home with a pool or hot tub in South Woodstock?
In South Woodstock, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, making it an excellent choice for travellers seeking relaxation and leisure. This picturesque town offers a charming rural setting, ideal for enjoying the natural beauty of the Green Mountains. Many of these properties come equipped with private pools or hot tubs, spacious outdoor areas, and well-appointed kitchens, allowing guests to unwind after a day of exploring.The area provides access to various outdoor activities, including hiking, cycling, and even skiing during the winter months, making these rentals superb for year-round getaways.
Are there pet-friendly house rentals in South Woodstock?
In South Woodstock, there are several pet-friendly house rentals available, offering a charming escape in the Vermont countryside. Many of these properties come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam and play.The area is known for its picturesque landscapes, providing a serene setting for nature walks and outdoor activities. Nearby, the Marsh-Billings-Rockefeller National Historical Park offers beautiful trails that are great for walking your dog while enjoying the stunning natural surroundings. Additionally, the quaint village atmosphere of South Woodstock features local shops and eateries that welcome pets, creating a delightful experience for both travellers and their furry companions.
Are there any remote work holiday rentals in South Woodstock?
In South Woodstock, Vermont, there are several holiday rentals suitable for remote work. These properties typically feature amenities such as dedicated desks and complimentary Wi-Fi, ensuring a productive environment for those working away from home. The serene surroundings offer a peaceful backdrop, ideal for focusing on work tasks while enjoying the beauty of the Vermont countryside.Travellers can expect comfortable accommodations with features that support both relaxation and productivity, allowing for a balanced experience of work and leisure. South Woodstock also provides access to local attractions, such as the picturesque Marsh-Billings-Rockefeller National Historical Park, where one can take breaks amidst nature. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in South Woodstock?
In South Woodstock, popular rental amenities include well-equipped kitchens that allow guests to prepare their own meals, balconies for enjoying the scenic views, and coffee and tea makers for a comforting start to the day. Additionally, many rentals come with desks and desk chairs, providing a functional workspace for those who may need to catch up on tasks during their stay.
When is the best time to visit South Woodstock for a holiday rental?
The best time to visit South Woodstock for a holiday rental is during the peak season from July to September, when the vibrant summer atmosphere draws visitors eager to experience the charm of Vermont. This period offers an abundance of outdoor activities like hiking the scenic trails, exploring nearby state parks, and enjoying the lush landscapes that come alive in the warm weather.In July, the town is particularly lively, with comfortable temperatures ranging from 15 to 25 degrees Celsius, great for outdoor adventures and leisurely strolls through the picturesque village. Many visitors take advantage of the beautiful conditions to engage in activities such as biking and enjoying local festivals, making it a great time to immerse yourself in the local culture.If you're looking for a more budget-friendly option, consider visiting in February. While this month is quieter, it offers a great experience with the serene beauty of winter landscapes. You can enjoy activities like snowshoeing or cross-country skiing, all while experiencing the peaceful charm of South Woodstock without the crowds.Ultimately, the best time for your visit will depend on whether you prefer the energetic summer vibe with plenty of outdoor activities or the tranquil beauty of winter for a more reflective escape.
What are the top attractions in South Woodstock?
In South Woodstock, visitors can enjoy a selection of picturesque attractions that highlight the area's natural beauty and charm. The Marsh-Billings-Rockefeller National Historical Park is a key highlight, offering scenic trails and a glimpse into the region's history of conservation and forestry. The park's walking paths are superb for leisurely hikes, and the historic mansion within the park is open for guided tours.The nearby Woodstock Village is also a must-visit, with its quaint shops, local eateries, and the iconic Woodstock Inn, which provides a lovely backdrop for a day of exploration. For those interested in outdoor activities, the Kedron Valley is great for hiking and enjoying the serene landscape.
Are all fees included in the South Woodstock holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any South Woodstock holiday homes with parking?
Stayz offers a wide selection of holiday homes in South Woodstock with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for South Woodstock holiday homes?
You can find great discounts on holiday homes in South Woodstock on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my South Woodstock holiday home booking on Stayz?
To find South Woodstock holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Woodstock?
A long-stay holiday home in South Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a South Woodstock holiday home?
Book your South Woodstock holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Woodstock?
Prices for holiday homes in South Woodstock vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Woodstock to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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