Winhall holiday rentals

We found 687 holiday rentals — enter your dates for availability
Select from 94 homes, 12 cottages and other holiday rentals in Winhall to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, which might include parking and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Winhall

Showing deals for:18 Dec - 25 Dec

Exterior
Exterior
Interior
Private kitchen
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
AU$34,937
for 7 nights, 1 home
AU$4,991 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
A look at the main floor family room from above.
Welcome to our 9 bedroom luxury home in the heart of Southern Vermont!
Complete privacy on our property!
Hot tub and firepit are great after a day of fun.
Exceptional
(22 reviews)

Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!

Bondville

8% off
AU$38,396
for 7 nights, 1 home
AU$5,485 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
Primary bedroom balcony
Interior
Sitting room looking into the kitchen.
Private kitchen
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,510
for 7 nights, 1 home
AU$2,216 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Private kitchen
Interior
Room
Dining
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,164
for 7 nights, 1 home
AU$3,452 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
View of the Main house living room from the kitchen bar
Main house top floor river room with sounds of the river out the windows.
2nd - 3rd floor main house stairs
View of the main house from the creek on the property.
Exceptional
(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off
AU$21,900
for 7 nights, 1 home
AU$3,129 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
View from mudroom
Living area
Back porch
Dining room
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,731
for 7 nights, 1 cabin
AU$533 per night
includes taxes & fees
Wishing Well Cabin
Antique Cabin
Porch -Summer
Antique Cabin
Porch - Winter
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,928
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
3-Season porch (new addition 2023)
Large open-concept living and kitchen area
Terrace/patio
Dining area
Exceptional
(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off
AU$8,501
for 7 nights, 1 cabin
AU$1,214 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Private kitchen
Interior
Interior
Dining
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
AU$17,630
for 7 nights, 1 home
AU$2,519 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Private kitchen
Exterior
Living area
Dining
Exceptional
(33 reviews)

Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.

Bondville

8% off
AU$9,140
for 7 nights, 1 chalet
AU$1,306 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Interior
Terrace/patio
Exterior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
AU$10,065
for 7 nights, 1 home
AU$1,438 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
Kitchen and dining Area - seats 9 with bench / 2 at counter
Living area
Dining
South side of house, deck and hot tub
Exceptional
(32 reviews)

Perfect Get-Away House - 6 Miles from Stratton & Mount Snow

West Wardsboro

5% off
AU$8,685
for 7 nights, 1 home
AU$1,241 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
Exterior
Property grounds
Room
Living area
Exceptional
(28 reviews)

Bear Pass Bunkhouse

Manchester

8% off
AU$3,075
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
Bear Pass Bunkhouse
Stratton mtn fire tower view
Outdoor dining
let it snow!
living room
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

8% off
AU$5,470
for 7 nights, 1 home
AU$781 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Living Room
Property grounds
Private kitchen
Exterior
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
AU$5,432
for 7 nights, 1 home
AU$776 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Wood burning stove 1
Large dining area accommodates family sized gatherings
Living Room
Welcome to Tallwood Timber VT
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

8% off
AU$6,455
for 7 nights, 1 home
AU$922 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Outdoor dining
Available weekend, weekly or monthly spring or summer rental.
Interior
Interior
Exceptional
(32 reviews)

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.

Jamaica

8% off
AU$4,329
for 7 nights, 1 apartment
AU$618 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
Living area
Exterior
Private kitchen
Pool
Exceptional
(21 reviews)

Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!

Bondville

8% off
AU$12,807
for 7 nights, 1 home
AU$1,830 per night
includes taxes & fees
Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!
Private kitchen
Exterior
Interior
Interior
Exceptional
(9 reviews)

Enchanting barn in E Dover with 50 mile view

East Dover

16% off
AU$2,437
for 7 nights, 1 home
AU$348 per night
includes taxes & fees
Enchanting barn in E Dover with 50 mile view
entrance view
deck
Living area
kitchen
Exceptional
(8 reviews)

Accessible Manchester Home with Amazing Views!

Manchester Center

8% off
AU$7,221
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Accessible Manchester Home with Amazing Views!
- Functional mudroom with wood bench and black modern accents - Hooks for coats and gear after outdoor adventures - Perfect transition space for guests exploring the outdoors
- Spacious open floor plan with bright natural lighting - Modern kitchen flows seamlessly into dining and living space - Ideal for entertaining with mountain views through large windows
- Sleek kitchen with black granite countertops and island seating - Fully equipped for cooking with stainless steel appliances - Open layout connects easily with living and dining area
- Bright outdoor patio with comfortable seating and green views - Perfect for morning coffee or relaxing afternoons outdoors - Peaceful setting surrounded by trees and mountain air
Exceptional
(6 reviews)

Escape to The Clyde’s View Hideaway in Manchester, Vt. New Home 3 Bed 2 Bath

Manchester Center

11% off
AU$5,755
for 7 nights, 1 home
AU$822 per night
includes taxes & fees
Escape to The Clyde’s View Hideaway in Manchester, Vt. New Home 3 Bed 2 Bath
Living area
Interior
Dining
Property grounds
Exceptional
(40 reviews)

Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking

Stratton

8% off
AU$18,149
for 7 nights, 1 apartment
AU$2,593 per night
includes taxes & fees
Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking
Living room with flat screen TV
Screened in porch with scenic view of private lake
Exposed Hand Hewn Beams
Summer 2015
Exceptional
(77 reviews)

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Bondville

8% off
AU$3,081
for 7 nights, 1 home
AU$440 per night
includes taxes & fees
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
- Lodge lobby with towering stone fireplace and leather seating - Rustic decor and cozy mountain lodge atmosphere - Perfect spot to unwind and connect after outdoor adventures
- Aerial view of resort with pool, paths, and lush greenery - Convenient location near trails and scenic mountain spots - Perfect for families and groups enjoying an outdoor escape
- Heated pool and hot tub with mountain views and privacy - Stone patio with lush landscaping and serene ambiance - Perfect for evening swims and relaxation after skiing
- Modern kitchen with granite counters and island seating - Overlooks cozy living room with fireplace and balcony view - Perfect for cooking and connecting with loved ones
Exceptional
(56 reviews)

Stratton base condo w/ pool & hot tub

Stratton

12% off
AU$18,436
for 7 nights, 1 apartment
AU$2,634 per night
includes taxes & fees
Stratton base condo w/ pool & hot tub

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Winhall getaway

Learn about the unique charm of Winhall with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Winhall

Are you hoping to find top things to see and do while you're in town? Venture out of your holiday home and check out everything that makes Winhall a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Stratton Mountain Golf Course (2.1 mi / 3.4 km)
  • Stratton Mountain Resort (3.8 mi / 6.1 km)
  • Bromley Mountain Ski Resort (4.7 mi / 7.5 km)
  • Jamaica State Park (5.3 mi / 8.5 km)
  • Golf Club at Equinox (7.9 mi / 12.8 km)
  • Magic Mountain Ski Resort (8 mi / 12.8 km)

Exploring the natural landscape of Winhall

Whether you're looking for adventure or just want to spend some time taking in the scenery, Winhall is a great place to spend some time outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Battenkill River (7 mi / 11.2 km)
  • Lowell Lake State Park (8.8 mi / 14.1 km)
  • Equinox Preservation Trust (8.9 mi / 14.3 km)
  • Emerald Lake State Park (9.8 mi / 15.8 km)
  • Mount Equinox (10.4 mi / 16.8 km)
  • Green Mountain National Forest (11.3 mi / 18.1 km)

Transport to and around Winhall

The nearest airport is in Springfield, VT (VSF-Hartness State), located 23.5 mi (37.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.7 mi (41.4 km) away.

Frequently asked questions

What is the best area to stay in Winhall when booking a holiday rental?
When considering a holiday rental in Winhall, Vermont, the area surrounding the Stratton Mountain Resort stands out as an excellent choice. This neighbourhood offers a delightful mix of outdoor activities and scenic beauty, making it a popular destination for visitors year-round. In winter, the resort transforms into a snowy playground, great for skiing and snowboarding, while in the summer, it provides ample opportunities for hiking and mountain biking.In addition to the resort, the nearby Green Mountain National Forest is a fantastic attraction, offering stunning landscapes and numerous trails for nature enthusiasts. For those who appreciate local culture, the charming village centre of Winhall features quaint shops and eateries that showcase the area's unique character.The region is home to a variety of properties, suiting different tastes and budgets, from cosy cabins to luxurious lodges, ensuring that visitors can find something that suits their needs.
When is the best time to visit Winhall for a holiday rental?
The best time to visit Winhall for a holiday rental is during the peak season from July to September. This vibrant period attracts outdoor enthusiasts and families alike, as the warm temperatures create the superb environment for activities like hiking, biking, and enjoying the natural beauty of Vermont's landscapes. With average daytime temperatures ranging from 20 to 25 degrees Celsius, visitors can comfortably explore the picturesque trails and enjoy the stunning views of the Green Mountains.July stands out as the most popular month, drawing a lively crowd eager to experience the local festivals, farmers' markets, and outdoor adventures. The atmosphere is buzzing with energy, making it an ideal time for family gatherings and socialising with fellow travellers.For those who might be seeking a more budget-friendly option, consider planning your visit in November. This quieter month allows you to enjoy the serene beauty of Winhall as the fall foliage transitions into winter, providing a great experience to appreciate the landscape without the hustle and bustle of peak season.
What are the top attractions in Winhall?
In Winhall, Vermont, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. Stratton Mountain Resort is a major draw, offering skiing and snowboarding in winter and mountain biking and hiking in the warmer months. The nearby Green Mountain National Forest provides stunning landscapes and numerous trails for those who enjoy hiking and exploring nature.For a taste of local culture, the quaint village of Bondville is close by, featuring charming shops and eateries. The area also hosts events throughout the year, including farmers' markets in the summer, where visitors can sample local produce and crafts.
Are all fees included in the Winhall 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 Winhall holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winhall 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 Winhall holiday homes?
You can find great discounts on holiday homes in Winhall 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 Winhall holiday home booking on Stayz?
To find Winhall 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 Winhall?
A long-stay holiday home in Winhall 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 Winhall holiday home?
Book your Winhall 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 Winhall?
Prices for holiday homes in Winhall 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 Winhall 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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