A sunset over a mountainous landscape with rocky outcrops and dense forest.

Winhall holiday lettings

We found 693 holiday rentals — enter your dates for availability

Select from 93 houses, 10 flats and other holiday rentals to find the perfect place for your stay in Winhall. 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:12 Feb - 19 Feb

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

Terrace/patio

Beautiful lakefront home located in Woods on Cole Pond. Near Stratton

Porch -Summer

Escape to This Ski Retreat Minutes from Stratton's Slopes and Village

Pool

Cozy Vermont Home Near Mount Snow & Stratton

Property grounds

Bear Pass Bunkhouse

Property grounds

Enchanting barn in E Dover with 50 mile view

Exterior

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Find the best place to stay - Winhall

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Image of Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Premier Host

Sleeps 12 · 4 bedrooms · 3+ bathrooms

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

Image of 3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

Premier Host

Sleeps 12 · 5 bedrooms · 3+ bathrooms

3 levels w/ Spectacular Mountain Views 8 minutes to either Stratton Base Lodge

Image of 3 levels w/ Spectacular Mountain Views
8 minutes to either Stratton Base Lodge

Premier Host

Sleeps 8 · 5 bedrooms · 4+ bathrooms

Designer 4-bedroom house in charming Stratton home sleeps 16

Image of Designer 4-bedroom house in charming Stratton home sleeps 16

Sleeps 14 · 4 bedrooms · 2+ bathrooms

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

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

Sleeps 10 · 4 bedrooms · 4 bathrooms

Summit View Ski and Golf Retreat w/hot tub & Sauna

Image of Summit View Ski and Golf Retreat w/hot tub & Sauna

Sleeps 8 · 4 bedrooms · 1+ bathroom

Holiday rentals with free cancellation in Winhall

Get a full refund when you cancel at least 30 days before check-in at these properties. Policies vary by property.

Heated Pool, Hot Tub, Outdoor Barrel Sauna, EV Charger, VIP Parking, Shuttle

Sunset exterior with stone chimney, deck and patio seating

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Outdoor spa tub

Mountain Chalet, sleeps 8, with hot tub

The caldron fire pit is a perfect source of radiated heat for cool spring or fall nights. We do provide firewood at the start of the season and do our best to keep a supply available.

Hot Tub, Game Room, Pool Table | Weekend Stratton Shuttle, 5BR

Sun-filled living room with vaulted wood ceiling and windows overlooking the Vermont woods

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

View from lower deck

Preferred Parking, Hot Tub, Sauna, EV Charger

Great room with indoor swing, sectional seating and doors to the mountain-view deck

Hot Tub, 2 Wood Fireplaces, En-Suite Every Bedroom | 9 Min to Stratton

Fire pit blazing at sunset outside Hilltop Hideaway in Winhall, Vermont

Long Trail House South Wing 2B2B Condo

Private kitchen

Cozy Mountain Townhouse with Fireplace near Stratton Mountain, Bondville, VT

Pool

Mountain retreat ideal for families year-round

Living area

Stratton Mountain Escape - 3BR, Fireplace, Shuttle, Pool & Hot Tub

Interior

Magnificent VIEWS at this Bromley Peru House!

Property grounds

3 Luxurious Levels of Living at this Bromley Willows Townhouse

Property grounds

The Fox Borrow at Bromley!

Interior

The spacious Ledges at Bromley!

Living area

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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