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Windham County vacation rentals

We found 1,893 vacation rentals — enter your dates for availability

Select from 633 houses, 98 apartments, and other vacation rentals to find the perfect place for your stay in Windham County. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Windham County

Showing deals for:Jun 19 - Jun 26

Image gallery for New Lakefront Log Home

Summer view from the lake
9.8 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

New Lakefront Log Home

Wilmington

13% off
Price is $689
$4,820 for 7 nights
All fees included
New Lakefront Log Home

Find spaces that suit your style

Find out more about Windham County

Why visit Windham County

  • Thrilling Ski Resorts: Windham County is home to fantastic ski resorts, perfect for winter sports enthusiasts.
  • Outdoor Adventures: Enjoy activities like hiking, biking, and water sports amid stunning natural landscapes.
  • Cultural Experiences: Explore local art galleries and historic neighborhoods that showcase the region's rich culture.
  • Serene Lakes: Relax by picturesque lakes, ideal for fishing, kayaking, or simply unwinding.
  • Diverse Accommodations: Choose from cozy cabins to luxurious rentals, catering to all preferences and budgets.

Popular types of accommodation in Windham County

Discover the perfect getaway in Windham County with Vrbo's diverse selection of vacation rentals. Whether you’re looking for a cozy cabin, a modern condo, or a spacious private home, we have listings that cater to every need. Many of our Vermont houses offer ground-floor options for easy access. Explore your ideal accommodations in Windham County, VT, and make unforgettable memories on your next vacation.

  • Houses: The top choice for travelers, offering spacious and comfortable stays for families or groups in Windham County.
  • Condos: A popular option for those seeking modern amenities and convenient locations, perfect for couples or small families.
  • Cabins: A charming retreat for nature lovers, providing a cozy atmosphere amidst the scenic beauty of Windham County.
  • Chalets: These distinctive lodgings blend rustic charm with comfort, ideal for a unique getaway experience.
  • Apartments: A practical choice for travelers wanting a home-like setting with easy access to local attractions.**

Top attractions in Windham County

Windham County, Vermont, is a fantastic destination for ski enthusiasts and adventure seekers alike. Visitors can explore a variety of attractions, including national parks, serene lakes, and art galleries. Whether you're looking for outdoor activities, cultural experiences, or family-friendly fun, this region offers something for everyone. Enjoy the natural beauty and rich local culture as you embark on your unforgettable vacation.

  • Brattleboro Common: This charming urban park offers a delightful atmosphere for families and city dwellers. With ample green space, it’s perfect for picnics, leisurely strolls, and outdoor activities, all while enjoying the vibrant community vibe.
  • Lake Raponda: A serene lake that exudes romance and beauty, Lake Raponda is ideal for outdoor enthusiasts. Enjoy swimming, sunbathing on the beach, or simply soaking in the picturesque scenery that surrounds the water.
  • Jamaica State Park: This national park is a haven for adventure seekers, featuring scenic trails and breathtaking views. Explore the lush landscapes, hike along the river, and immerse yourself in the great outdoors.

Things to do recommended for couples

For a romantic getaway in Windham County, indulge in a round of golf at the Brattleboro Country Club, where luxury meets scenic beauty. Afterward, explore quaint local shops and enjoy a cozy dinner at a charming restaurant for a memorable evening together.

Things to do recommended for families

Your family vacation in Windham County, Vermont, can include thrilling activities like visiting the local farms for berry picking, exploring the scenic trails at the Green Mountain National Forest, and enjoying seasonal festivals. Don't miss out on the fun at the nearby water parks for a refreshing day.

Things to do recommended for groups

Groups visiting Windham County can enjoy hiking the scenic trails of Mount Monadnock, explore the charming village of Weston with its artisan shops, and experience a wine tasting at local vineyards. Don't miss the vibrant farmers' markets for a taste of Vermont's freshest produce.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windham County

If you’re traveling with a group, family, or pets, or if you’re considering longer stays, be sure to apply the appropriate filters for your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Windham County with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Windham County with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windham County: For many families, a trip isn’t truly complete without their furry companion by their side. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windham County: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windham County

Windham County, Vermont, offers an unforgettable vacation experience, perfect for adventure seekers and families alike. With its stunning ski resorts and charming historic neighborhoods, visitors can enjoy a friendly atmosphere while exploring the picturesque landscapes. Whether you're looking for budget-friendly options or luxurious stays, Windham County caters to all. Discover quaint homes for sale, indulge in outdoor sports, or simply relax amidst the beautiful surroundings—there's something for everyone in this delightful region.

  • Stratton: Nestled in the heart of Windham County, Stratton is a premier destination for outdoor enthusiasts. Known for its exceptional skiing, this vibrant city boasts a top-notch ski resort that attracts visitors from all over. Alongside thrilling slopes, travelers can enjoy breathtaking views of the surrounding mountains and the serene Stratton Lake. The nearby national and state parks provide ample opportunities for hiking, mountain biking, and exploring the stunning natural landscape. Whether you're hitting the slopes in winter or enjoying summer adventures, Stratton promises an unforgettable experience.
  • West Dover: Just a stone's throw from Stratton, West Dover is another gem in Windham County that offers a similar allure for adventure seekers. This charming city is well-known for its ski fields and resorts, making it a fantastic winter getaway. In addition to skiing, visitors can revel in the beauty of the nearby lakes and mountains, perfect for summer recreation like fishing, kayaking, and hiking. West Dover's warm community atmosphere and stunning scenery create a perfect backdrop for both relaxation and thrilling outdoor activities.
  • Brattleboro: As one of the larger towns in Windham County, Brattleboro offers a unique blend of outdoor adventure and cultural experiences. While it may not be as ski-focused as Stratton and West Dover, it is an excellent base for exploring the nearby mountains and lakes. Brattleboro is also known for its vibrant arts scene, with galleries, theaters, and local shops that showcase the talent of the community. Visitors can enjoy outdoor activities in the surrounding national and state parks, making it an ideal spot for those seeking both adventure and culture.

Booking with Vrbo is simple

Are you eager to save on your upcoming travel plans? We recommend having some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for an extended stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you can quickly access exclusive member savings and earn OneKeyCash on eligible reservations. Sign up today to start enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last stopped, or organize your travel plans all in one place. You'll find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The captivating area of Windham County awaits your stay

The area's entertainment and monuments are just a few of the reasons to vacation in Windham County. Renowned for its skiing, shopping and snowboarding, this city welcomes all visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windham County

Do you want to find top things to see and do during your stay? Travelers enjoy Windham County for its skiing, snowboarding and hiking. Venture out of your cozy vacation rental and experience everything that Windham County has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Stratton Mountain Resort (15 mi / 24.2 km)
  • Harris Hill Ski Jump (9.8 mi / 15.7 km)
  • Mount Snow Golf Course (11.2 mi / 18 km)
  • The Hermitage Golf Club (13.2 mi / 21.2 km)
  • The Hermitage Club (13.3 mi / 21.4 km)
  • Mount Snow (13.5 mi / 21.7 km)

Exploring the mountains and other natural features in Windham County

Whether you're looking for adventure or just want to appreciate the scenery, Windham County is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Brattleboro Common (10.1 mi / 16.3 km)
  • Wantastiquet Mountain (10.3 mi / 16.6 km)
  • Madame Sherris Castle Ruins (10.8 mi / 17.4 km)
  • Madame Sherri Forest (10.9 mi / 17.5 km)
  • Hogback Mountain Conservation Area (11.1 mi / 17.9 km)
  • Lake Raponda (11.2 mi / 18.1 km)

Transportation options to and around Windham County

If you'd rather travel by train, make your way to Brattleboro Station or Bellows Falls Station to see more of the city.

Frequently asked questions

What is the best area to stay in Windham County when booking a vacation rental?
One of the most sought-after areas to book your vacation home in Windham County is Wilmington. Spend your trip here and visit some top attractions, including Lake Raponda and The Ledge.
What is the most popular type of vacation rental accommodation in Windham County?
The most sought-after types of vacation rentals in Windham County are condos. After something a little different? Vrbo has numerous options to match the diverse needs of our guests, so you'll see properties in all sizes, and for all budgets. The ideal fit is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Windham County?
Different things influence what you'll pay for a vacation rental in Windham County, such as the time of year, property type and length of stay. Still, all of our vacation homes have one thing in common — exceptional value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Windham County?
Prices for beach houses in Windham County may vary depending on the size and style of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and how many guests to view your rental options and prices. From there you can use our filter tool to tailor your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Windham County?
Yes. You'll have a choice of 133 vacation rentals that cater to pets in Windham County. Several of our pet-friendly vacation rentals even come with an outdoor space for your furry pal to run around in, dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
Are there large group vacation rentals in Windham County?
With 356 properties that can sleep 10 guests or more in Windham County, you don't have to hold back on your invites. From extended family vacations to events like Christmas or New Year's Eve parties, Vrbo can help you find a large group rental to match the occasion.
Are there one-bedroom vacation rentals in Windham County?
Yes, Windham County has 106 one-bedroom rentals available. Typically located in sought-after areas because of their smaller size, a one-bedroom property is perfect if you're getting away with a friend or your partner. And with comforts like full kitchens and more privacy, you'll be able to relax while sightseeing around this incredible destination.
Can I find two-bedroom vacation rentals in Windham County?
Take off with your loved ones and enjoy peace, privacy and comfort in one of the 135 two-bedroom vacation properties Windham County has to offer.
Are there vacation rentals with WiFi in Windham County?
Whether you want to stay in touch with world events, check emails or update your social media accounts, there are 362 vacation homes with WiFi in Windham County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Windham County?
Windham County has 300 vacation rentals where you can relax in air-conditioned comfort. To book a property on Vrbo offering this perk, enter your dates of travel and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Windham County?
The minimum required age is generally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Windham County stay before making a booking.
How long can I rent a vacation rental in Windham County for?
The amount of time you can rent a Windham County vacation home for is down to the property. Just put in your dates of travel to browse available options that offer extended stays. They feature all the things you need to make your extended trip more enjoyable and convenient, like air conditioning and laundries. Some Vrbo vacation homes may also offer weekly or monthly discounts, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Windham County?
Short break or a well-deserved long vacation, Vrbo has some great deals and discounted options in Windham County that'll suit your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what's recently been added with one of our newly listed homes. Whatever kind of getaway you're after, you'll find the ideal place to stay — at an affordable rate.

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