Winhall holiday homes

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

Interior
Exterior
Sports court
Exterior
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
NZ$43,731
for 7 nights, 1 home
NZ$6,247 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
NZ$48,519
for 7 nights, 1 home
NZ$6,931 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
View from upstairs guest room
Interior
Sitting room looking into the kitchen.
Primary bedroom balcony
Exceptional
(8 reviews)

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

Bondville

8% off
NZ$19,314
for 7 nights, 1 home
NZ$2,759 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Antique Cabin
Porch -Summer
Exterior
Antique Cabin
Exceptional
(89 reviews)

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

Jamaica

8% off
NZ$7,490
for 7 nights, 1 home
NZ$1,070 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Room
Interior
Bar (on property)
Private kitchen
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
NZ$30,283
for 7 nights, 1 home
NZ$4,326 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Interior
Interior
Dining
Exterior
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
NZ$22,280
for 7 nights, 1 home
NZ$3,183 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Dining area
Large open-concept living and kitchen area
Bedroom 1: Queen Bed
3-Season porch (new addition 2023)
Exceptional
(18 reviews)

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

Wardsboro

8% off
NZ$10,712
for 7 nights, 1 cabin
NZ$1,530 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Living area
Exterior
Private kitchen
Plenty of room for relaxing.
Exceptional
(33 reviews)

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

Bondville

8% off
NZ$11,571
for 7 nights, 1 chalet
NZ$1,653 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
NZ$12,720
for 7 nights, 1 home
NZ$1,817 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
let it snow!
Outdoor dining
Stratton mtn fire tower view
main entrance
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

7% off
NZ$6,913
for 7 nights, 1 home
NZ$988 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Kitchen and dining Area - seats 9 with bench / 2 at counter
Living area
Loft with surround sound Entertainment
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
NZ$10,989
for 7 nights, 1 home
NZ$1,570 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
NZ$3,887
for 7 nights, 1 home
NZ$555 per night
includes taxes & fees
Bear Pass Bunkhouse
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
NZ$8,128
for 7 nights, 1 home
NZ$1,161 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Living area
Exterior
Pool
Private kitchen
Exceptional
(21 reviews)

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

Bondville

8% off
NZ$15,897
for 7 nights, 1 home
NZ$2,271 per night
includes taxes & fees
Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!
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
NZ$5,472
for 7 nights, 1 apartment
NZ$782 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
Living area
deck
kitchen
entrance view
Exceptional
(8 reviews)

Accessible Manchester Home with Amazing Views!

Manchester Center

8% off
NZ$9,123
for 7 nights, 1 home
NZ$1,303 per night
includes taxes & fees
Accessible Manchester Home with Amazing Views!
Private kitchen
Exterior
Interior
Interior
Exceptional
(9 reviews)

Enchanting barn in E Dover with 50 mile view

East Dover

16% off
NZ$3,019
for 7 nights, 1 home
NZ$431 per night
includes taxes & fees
Enchanting barn in E Dover with 50 mile view
Exposed Hand Hewn Beams
Screened in porch with scenic view of private lake
Favorite haunt sun-glass porch
Living room with flat screen TV
Exceptional
(77 reviews)

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

Bondville

8% off
NZ$3,894
for 7 nights, 1 home
NZ$556 per night
includes taxes & fees
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Property grounds
Interior
Private kitchen
Dining
Exceptional
(40 reviews)

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

Stratton

8% off
NZ$22,669
for 7 nights, 1 apartment
NZ$3,238 per night
includes taxes & fees
Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking
Kitchen
Entering the condo view, living room, kitchen & dining room
Living area
Living area
Exceptional
(14 reviews)

Stratton Mountain-Spacious Multi-Level 1830 Ft. Premium Townhouse

Bondville

8% off
NZ$10,832
for 7 nights, 1 apartment
NZ$1,547 per night
includes taxes & fees
Stratton Mountain-Spacious Multi-Level 1830 Ft. Premium Townhouse
Room
Interior
Exterior
Private kitchen
Exceptional
(23 reviews)

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

Dorset

8% off
NZ$2,628
for 7 nights, 1 apartment
NZ$375 per night
includes taxes & fees
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • 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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Winhall holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Winhall to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.