Windham holiday homes

We found 674 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Windham that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Windham

Showing deals for:18 Dec - 25 Dec

Exterior
Exterior
Private kitchen
Interior
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
NZ$43,300
for 7 nights, 1 home
NZ$6,186 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
Deer Room - 1st floor bedroom with a queen bed.
Fully stocked kitchen with plenty of room to prepare a family dinner
The first floors open plan is great for large groups.
Welcome to the Blue Moon Bungalow!
Exceptional
(11 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester

8% off
NZ$6,153
for 7 nights, 1 chalet
NZ$879 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
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
NZ$45,398
for 7 nights, 1 home
NZ$6,485 per night
includes taxes & fees
September & October available! Luxury 9BRs Stratton Estate. Pool, Mountain Views
Primary bedroom balcony
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
NZ$19,124
for 7 nights, 1 home
NZ$2,732 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Dining
Interior
Private kitchen
Bar (on property)
Exceptional
(78 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
NZ$29,985
for 7 nights, 1 home
NZ$4,284 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
View of the main house from the creek on the property.
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
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
NZ$27,164
for 7 nights, 1 home
NZ$3,881 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Front door
Living area
Dining room
View from mudroom
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

7% off
NZ$4,708
for 7 nights, 1 cabin
NZ$673 per night
includes taxes & fees
Wishing Well Cabin
Porch - Winter
Porch -Summer
Antique Cabin
Exterior
Exceptional
(89 reviews)

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

Jamaica

8% off
NZ$7,357
for 7 nights, 1 home
NZ$1,051 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Terrace/patio
Large open-concept living and kitchen area
3-Season porch (new addition 2023)
Bedroom 1: Queen Bed
Exceptional
(18 reviews)

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

Wardsboro

8% off
NZ$10,634
for 7 nights, 1 cabin
NZ$1,519 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Plenty of room for relaxing.
Exterior
Private kitchen
Dining
Exceptional
(33 reviews)

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

Bondville

8% off
NZ$11,457
for 7 nights, 1 chalet
NZ$1,637 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
Bedroom #2 Queen bed with large windows & french doors
Front of house, early spring
Open living room with french doors, huge windows & vaulted ceiling
Light filled kitchen
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
NZ$7,262
for 7 nights, 1 home
NZ$1,037 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Screened in porch dining area
Property grounds
Living Room
Private kitchen
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
NZ$6,800
for 7 nights, 1 home
NZ$971 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Welcome to Tallwood Timber VT
Large dining area accommodates family sized gatherings
Backyard - Fire Pit area
Wood burning stove 1
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

8% off
NZ$8,048
for 7 nights, 1 home
NZ$1,150 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Interior
Exterior
Terrace/patio
Interior
Exceptional
(73 reviews)

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Chester

8% off
NZ$3,484
for 7 nights, 1 cabin
NZ$498 per night
includes taxes & fees
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Outdoor dining
Available weekend, weekly or monthly spring or summer rental.
Interior
Private kitchen
Exceptional
(32 reviews)

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

Jamaica

8% off
NZ$5,424
for 7 nights, 1 apartment
NZ$775 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
Private kitchen
Exterior
Living area
Pool
Exceptional
(21 reviews)

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

Bondville

8% off
NZ$15,740
for 7 nights, 1 home
NZ$2,249 per night
includes taxes & fees
Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!
Dining
Interior
Property grounds
Private kitchen
Exceptional
(40 reviews)

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

Stratton

8% off
NZ$22,446
for 7 nights, 1 apartment
NZ$3,207 per night
includes taxes & fees
Newly Renovated 2BR - walk to lift; walk to Stratton Village; easy parking
- Vibrant fall view with mountains and colorful forest canopy   - Breathtaking seasonal scenery from your private balcony   - Capture nature’s beauty from this mountain getaway
- 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
- 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
- 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
Exceptional
(56 reviews)

Stratton base condo w/ pool & hot tub

Stratton

12% off
NZ$22,806
for 7 nights, 1 apartment
NZ$3,258 per night
includes taxes & fees
Stratton base condo w/ pool & hot tub
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
Village Watch #4 prime location overlooking Tamarack Chairlift & trail
Exceptional
(93 reviews)

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

Stratton

8% off
NZ$14,212
for 7 nights, 1 apartment
NZ$2,030 per night
includes taxes & fees
Beautiful -Slope-side- Stratton Mountain Condo, Walk to Chairlift, Village & Gym
Living area
Entering the condo view, living room, kitchen & dining room
Kitchen
A14
Exceptional
(14 reviews)

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

Bondville

8% off
NZ$10,725
for 7 nights, 1 apartment
NZ$1,532 per night
includes taxes & fees
Stratton Mountain-Spacious Multi-Level 1830 Ft. Premium Townhouse
Dining table and chairs for 8 people.
An electric fireplace heater sits in the corner of the sitting area.
Outside view of the apartment, enter through the double doors on the deck
Compact but fully loaded kitchen
Exceptional
(11 reviews)

Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16

Londonderry

8% off
NZ$4,889
for 7 nights, 1 apartment
NZ$698 per night
includes taxes & fees
Apartment at Viking Nordic Center; sleeps 6. Rent with The Farmhouse to sleep 16
Exterior
Dining
Living area
Private kitchen
Exceptional
(22 reviews)

Charming Chester Farmhouse near Near VT Slopes

Chester

8% off
NZ$8,996
for 7 nights, 1 home
NZ$1,285 per night
includes taxes & fees
Charming Chester Farmhouse near Near VT Slopes
- Bright and airy living space with cozy fireplace and lodge vibes   - Mountain décor and tall ceilings create an inviting retreat   - Steps from Stratton slopes with stunning scenic views
- Charming resort exterior with pond, fountain, and mountain views   - Peaceful landscaped grounds perfect for strolls and photos   - Relaxed alpine escape in the heart of Stratton Village
- Open-concept kitchen with granite countertops and rustic bar seating   - Bright living area with mountain charm and warm cabin décor   - Ideal for family meals after a day on Stratton slopes
- Elegant lodge lobby with grand stone fireplace and cozy seating   - Warm mountain ambiance with rustic décor and high-beamed ceiling   - Inviting gathering space after a day on Stratton slopes
Exceptional
(12 reviews)

Mountain condo w/ heated pool & fire pit

Stratton

12% off
NZ$23,104
for 7 nights, 1 apartment
NZ$3,301 per night
includes taxes & fees
Mountain condo w/ heated pool & fire pit
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

Choose a holiday rental for your Windham getaway

Learn about the unique charm of Windham with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Windham

Are you hoping to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Windham a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Magic Mountain Ski Resort (2.6 mi / 4.2 km)
  • Jamaica State Park (4.7 mi / 7.6 km)
  • Viking Nordic Center (4.7 mi / 7.6 km)
  • Stratton Mountain Golf Course (9.7 mi / 15.7 km)
  • Stratton Mountain Resort (10.6 mi / 17.1 km)
  • Vermont Country Store (11.1 mi / 17.9 km)

Exploring the natural landscape of Windham

Whether you're an adventurous traveller or just want to appreciate the scenery, Windham is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (4 mi / 6.5 km)
  • Winhall River (6.2 mi / 10 km)
  • Emerald Lake State Park (16 mi / 25.8 km)
  • Lye Brook Falls (16.2 mi / 26.1 km)
  • Battenkill River (16.4 mi / 26.5 km)
  • Green Mountain National Forest (16.9 mi / 27.2 km)

Transport to and around Windham

The nearest airport is in Springfield, VT (VSF-Hartness State), located 15.5 mi (24.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 26.9 mi (43.3 km) away.

Frequently asked questions

What is the best area to stay in Windham when booking a holiday rental?
When considering a holiday rental in Windham, Vermont, the area surrounding the quaint village is a fantastic option. This picturesque part of the state offers a charming blend of natural beauty and local attractions. The surrounding countryside is dotted with various properties that capture the essence of Vermont's rustic appeal, providing a serene retreat for visitors.Among the highlights in Windham, the nearby Magic Mountain Ski Area is a popular choice for winter sports enthusiasts, offering a range of slopes suitable for all skill levels. In addition, the area boasts stunning hiking trails, such as those leading to the scenic views at the summit of nearby Mount Snow, which are superb for outdoor lovers during the warmer months.Another popular aspect of Windham is its proximity to the vibrant local culture, with opportunities to explore art galleries, farmer's markets, and seasonal festivals that celebrate the region's heritage.
When is the best time to visit Windham for a holiday rental?
March is the most popular month to visit Windham, Vermont, especially for those eager to embrace the winter wonderland that the region has to offer. During this time, the snow conditions are often at their peak, making it ideal for skiing, snowboarding, and enjoying the beautiful snowy landscapes. The charming village atmosphere combined with outdoor activities creates a vibrant experience for visitors.As spring approaches, April begins to usher in a milder climate, with temperatures starting to rise from the chill of winter, averaging around 5 to 15 degrees Celsius. This transition period is great for those who appreciate the quieter moments of nature, with opportunities for early hiking and exploring the local scenery as the snow melts away.The high tourist season in Windham typically runs from July to September, attracting visitors keen on summer activities like hiking, biking, and enjoying local festivals. However, for travellers seeking a more tranquil experience, December offers a unique charm with fewer crowds, allowing for a peaceful retreat amidst the festive winter decorations.For those who are budget-conscious yet still want to enjoy the beauty of Windham, consider visiting in late March or early April. This time not only provides a chance to enjoy the tail end of the skiing season but also to witness the early signs of spring, making it an excellent value for your holiday rental.
What are the top attractions in Windham?
In Windham, Vermont, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Windham Mountain Resort is a popular destination for skiing and snowboarding during the winter months, offering various trails for all skill levels. In the warmer seasons, the resort transforms into a hub for mountain biking and hiking, with picturesque trails that showcase the stunning landscapes.The charming local community is also home to several quaint shops and eateries that reflect the New England character. Nearby, the scenic Green Mountain National Forest provides ample opportunities for outdoor enthusiasts to explore, with hiking trails, lakes, and picnic spots. Additionally, the area around the West River features beautiful views and is ideal for fishing, kayaking, and enjoying leisurely walks along the riverbank.
Are all fees included in the Windham 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 Windham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Windham 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 Windham holiday homes?
You can find great discounts on holiday homes in Windham 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 Windham holiday home booking on Bookabach?
To find Windham 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 Windham?
A long-stay holiday home in Windham 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 Windham holiday home?
Book your Windham 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 Windham?
Prices for holiday homes in Windham 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 Windham 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.