Winhall holiday lettings

We found 695 holiday rentals — enter your dates for availability
Select from 98 homes, 13 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:4 Dec - 11 Dec

Exterior
Living area
Room
Exterior
Exceptional
(7 reviews)

Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

Bondville

11% off
£4,200
for 7 nights, 1 chalet
£600 per night
includes taxes & fees
Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms
Interior
Exterior
Private kitchen
Sports court
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
£17,018
for 7 nights, 1 home
£2,431 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)

September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views

Bondville

8% off
£14,513
for 7 nights, 1 home
£2,073 per night
includes taxes & fees
September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views
Private kitchen
Interior
View from upstairs guest room
Sitting room looking into the kitchen.
Exceptional
(8 reviews)

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

Bondville

8% off
£8,824
for 7 nights, 1 home
£1,261 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Main house top floor river room with deck overlooking the pool and backyard.
Main house top floor river room with sounds of the river out the windows.
View of the Main house living room from the kitchen bar
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
£12,003
for 7 nights, 1 home
£1,715 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
View of the living area from the loft.
Large windows allowing natural light in.
Upstairs entry to mudroom.
Hot tub on a cold night.
Exceptional
(16 reviews)

Mountain House near Mount Snow & Stratton w/ 2 Fireplaces, Hot Tub & Sauna

Wardsboro

7% off
£3,530
for 7 nights, 1 cabin
£504 per night
includes taxes & fees
Mountain House near Mount Snow & Stratton w/ 2 Fireplaces, Hot Tub & Sauna
Dining
Interior
Exterior
Private kitchen
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
£7,944
for 7 nights, 1 home
£1,135 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Upper level
Living room
View of loft bedroom
Exterior
Exceptional
(8 reviews)

Family Friendly Stratton Home for All Seasons, 7 min to ski mountain

Bondville

8% off
£6,402
for 7 nights, 1 home
£915 per night
includes taxes & fees
Family Friendly Stratton Home for All Seasons, 7 min to ski mountain
Private kitchen
Interior
Room
Bar (on property)
Exceptional
(77 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

19% off
£5,539
for 7 nights, 1 home
£791 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Outdoor spa tub
One of a kind woodwork, beautiful handmade furniture and built ins.....
The tile work in all bathrooms and kitchen are unique hand made tiles
Inside, Outside - take your pick - it's always magical
Exceptional
(53 reviews)

One of a Kind Post and Beam Home on Private 100 acre Island

Jamaica

8% off
£5,089
for 7 nights, 1 home
£727 per night
includes taxes & fees
One of a Kind Post and Beam Home on Private 100 acre Island
Exterior
Interior
Private kitchen
Living area
Exceptional
(7 reviews)

Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!

Bondville

8% off
£13,729
for 7 nights, 1 home
£1,961 per night
includes taxes & fees
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
Interior
Terrace/patio
Interior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
£5,566
for 7 nights, 1 home
£795 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
3-Season porch (new addition 2023)
Large open-concept living and kitchen area
Dining area
Terrace/patio
Exceptional
(18 reviews)

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

Wardsboro

8% off
£2,675
for 7 nights, 1 cabin
£382 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
living room
Outdoor dining
Stratton mtn fire tower view
main entrance
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

7% off
£2,707
for 7 nights, 1 home
£387 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Kitchen and dining Area - seats 9 with bench / 2 at counter
Living area
Dining
Loft with surround sound Entertainment
Exceptional
(32 reviews)

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

West Wardsboro

5% off
£4,856
for 7 nights, 1 home
£694 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
- Rustic living room with a grand stone fireplace and mountain lodge charm   - Cozy seating, wood beams, and large windows for natural light   - Perfect for relaxing after skiing or mountain adventures
- Relaxing hot tub with forest and snow views for ultimate serenity   - Covered deck with private spa perfect for chilly nights   - Mountain cabin stay offering true relaxation and luxury comfort
- Bright open living area with stone fireplace and timber beams   - Rustic modern decor blending warmth and mountain style   - Ideal cabin stay for family gatherings and cozy nights
- Stunning view of colorful fall trees surrounding the cabin   - Perfect for autumn walks and cozy nights by the fire   - Experience Vermont’s breathtaking seasonal beauty
Exceptional
(14 reviews)

Cozy chalet w/ hot tub & fire pit

Stratton

11% off
£8,178
for 7 nights, 1 chalet
£1,168 per night
includes taxes & fees
Cozy chalet w/ hot tub & fire pit
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

7% off
£3,662
for 7 nights, 1 home
£523 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Private kitchen
Property grounds
Living area
Room
Exceptional
(26 reviews)

Bear Pass Bunkhouse

Manchester

8% off
£1,693
for 7 nights, 1 home
£242 per night
includes taxes & fees
Bear Pass Bunkhouse
Private kitchen
Exterior
Plenty of room for relaxing.
Living area
Exceptional
(33 reviews)

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

Bondville

8% off
£4,134
for 7 nights, 1 chalet
£591 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Living area
Property grounds
Dining
Exterior
Exceptional
(24 reviews)

Gorgeous Mountain View in Manchester, Shopping, Dining, Spa. 5 min walk to town.

Manchester

7% off
£3,772
for 7 nights, 1 home
£539 per night
includes taxes & fees
Gorgeous Mountain View in Manchester, Shopping, Dining, Spa. 5 min walk to town.
Extensive glass overlooking deck & pond
Living area
upstairs living room and kitchen area.
Open free form decks
Exceptional
(255 reviews)

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Bondville

8% off
£1,327
for 7 nights, 1 cottage
£190 per night
includes taxes & fees
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Fully enclosed loft space
Newly renovated kitchen with all major appliance, utensils, pots and pans.
Another view of our dining room and newly renovated kitchen.
Interior
Exceptional
(9 reviews)

Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!

Manchester Center

11% off
£2,113
for 7 nights, 1 cabin
£302 per night
includes taxes & fees
Cozy Cabin - walking distance to town and 10 minutes to Bromley. Pet friendly!
Screened in porch dining area
Property grounds
Living Room
Exterior
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
£1,919
for 7 nights, 1 home
£274 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Interior
Available weekend, weekly or monthly spring or summer rental.
Outdoor dining
Private kitchen
Exceptional
(32 reviews)

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

Jamaica

8% off
£2,352
for 7 nights, 1 apartment
£336 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
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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.
How much does it cost to rent a holiday home in Winhall?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winhall to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winhall holiday house rentals?
You can find great discounts on house rentals in Winhall on Vrbo, 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 find long-stay holiday rentals in Winhall?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Winhall holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Winhall holiday rental?
Book your Winhall holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Winhall home rental booking on Vrbo?
To find Winhall holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winhall holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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