Winhall holiday lettings

We found 689 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

Private kitchen
Exterior
Sports court
Exterior
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
£19,212
for 7 nights, 1 home
£2,745 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
£20,201
for 7 nights, 1 home
£2,886 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
Private kitchen
Interior
Room
Bar (on property)
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

16% off
£13,509
for 7 nights, 1 home
£1,930 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Sitting room looking into the kitchen.
Interior
Private kitchen
View from upstairs guest room
Exceptional
(8 reviews)

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

Bondville

8% off
£8,833
for 7 nights, 1 home
£1,262 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
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
Main house top floor river room with deck overlooking the pool and backyard.
Exceptional
(38 reviews)

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

Wardsboro

8% off
£12,016
for 7 nights, 1 home
£1,717 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Private kitchen
Interior
Dining
Interior
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
£9,276
for 7 nights, 1 home
£1,325 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Exterior
Porch -Summer
Porch - Winter
Antique Cabin
Exceptional
(89 reviews)

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

Jamaica

8% off
£3,119
for 7 nights, 1 home
£446 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
Dining area
Bedroom 1: Queen Bed
Exceptional
(18 reviews)

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

Wardsboro

8% off
£4,479
for 7 nights, 1 cabin
£640 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Dining room
Living area
Front door
View from mudroom
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

7% off
£2,047
for 7 nights, 1 cabin
£292 per night
includes taxes & fees
Wishing Well Cabin
Plenty of room for relaxing.
Exterior
Dining
Private kitchen
Exceptional
(33 reviews)

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

Bondville

8% off
£5,045
for 7 nights, 1 chalet
£721 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Exterior
Terrace/patio
Interior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
£5,296
for 7 nights, 1 home
£757 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
let it snow!
Outdoor dining
main entrance
Stratton mtn fire tower view
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

8% off
£2,878
for 7 nights, 1 home
£411 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
South side of house, deck and hot tub
Living area
Dining
Kitchen and dining Area - seats 9 with bench / 2 at counter
Exceptional
(32 reviews)

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

West Wardsboro

5% off
£4,861
for 7 nights, 1 home
£694 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
Living area
Property grounds
Exterior
Room
Exceptional
(28 reviews)

Bear Pass Bunkhouse

Manchester

8% off
£1,619
for 7 nights, 1 home
£231 per night
includes taxes & fees
Bear Pass Bunkhouse
Living Room
Property grounds
Exterior
Screened in porch dining area
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
£3,013
for 7 nights, 1 home
£430 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Wood burning stove 1
Large dining area accommodates family sized gatherings
Backyard - Fire Pit area
Welcome to Tallwood Timber VT
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

7% off
£3,666
for 7 nights, 1 home
£524 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Private kitchen
Available weekend, weekly or monthly spring or summer rental.
Interior
Outdoor dining
Exceptional
(32 reviews)

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

Jamaica

8% off
£2,278
for 7 nights, 1 apartment
£325 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
Private kitchen
Exterior
Pool
Room
Exceptional
(21 reviews)

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

Bondville

8% off
£7,083
for 7 nights, 1 home
£1,012 per night
includes taxes & fees
Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!
Interior
Exterior
Interior
Living area
Exceptional
(9 reviews)

Enchanting barn in E Dover with 50 mile view

East Dover

16% off
£1,297
for 7 nights, 1 home
£185 per night
includes taxes & fees
Enchanting barn in E Dover with 50 mile view
rear of house
deck
entrance view
Living area
Exceptional
(8 reviews)

Accessible Manchester Home with Amazing Views!

Manchester Center

8% off
£3,799
for 7 nights, 1 home
£543 per night
includes taxes & fees
Accessible Manchester Home with Amazing Views!
Property grounds
Interior
Private kitchen
Living area
Exceptional
(40 reviews)

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

Stratton

8% off
£9,823
for 7 nights, 1 apartment
£1,403 per night
includes taxes & fees
Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking
- Open dining area with rustic wooden table and modern chairs   - Seamless access to patio and backyard through sliding doors   - Ideal for group meals with mountain view ambiance
- 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
- 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
- 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
Exceptional
(6 reviews)

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

Manchester Center

11% off
£3,027
for 7 nights, 1 home
£432 per night
includes taxes & fees
Escape to The Clyde’s View Hideaway in Manchester, Vt. New Home 3 Bed 2 Bath
Master Bedroom with walk out patio
Completely new, Hi-end Kitchen with granite countertops & lots of cabinet space
Kitchen island & Family Room with wood burning fireplace
Mudroom & Laundry located just off the kitchen
Exceptional
(93 reviews)

Beautiful -Slope-side- Stratton Mountain Condo, Walk to Chairlift, Village & Gym

Stratton

8% off
£6,271
for 7 nights, 1 apartment
£896 per night
includes taxes & fees
Beautiful -Slope-side- Stratton Mountain Condo, Walk to Chairlift, Village & Gym
- 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
- 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
- Vibrant fall view with mountains and colorful forest canopy   - Breathtaking seasonal scenery from your private balcony   - Capture nature’s beauty from this mountain getaway
Exceptional
(56 reviews)

Stratton base condo w/ pool & hot tub

Stratton

12% off
£10,022
for 7 nights, 1 apartment
£1,432 per night
includes taxes & fees
Stratton base condo w/ pool & hot tub
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    Enjoy full kitchens, pools, gardens and more
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    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.
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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