Best Vacation Homes in Windham County
1000 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
£139/Night
For 7 Nights £970
947.22 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Beach
- Skiing
- Fireplace/Heating
£249/Night
For 7 Nights £1,740
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Spa
- Fireplace/Heating
- Balcony/Terrace
£154/Night
For 7 Nights £1,078
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£138/Night
For 7 Nights £968
2079.59 ft²
20 Guests
10 Bedrooms
12 Bathrooms
Bed & Breakfast
- Private Pool
- Private Beach
- Oceanfront
£464/Night
For 7 Nights £3,250
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Skiing
- Fireplace/Heating
- Pool
£129/Night
For 7 Nights £902
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Skiing
£213/Night
For 7 Nights £1,492
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Spa
- Fireplace/Heating
£161/Night
For 7 Nights £1,125
Windham County Luxury Rentals
15000 ft²
54 Guests
21 Bedrooms
19 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
£2,850/Night
For 7 Nights £19,953
6996.54 ft²
27 Guests
10 Bedrooms
7 Bathrooms
Free Cancellation
House
- Oceanfront
- Hot Tub
- Skiing
£2,721/Night
For 7 Nights £19,048
1 Bathroom
Couples Retreat
Hotel
- Skiing
- Fireplace/Heating
- Parking
£2,627/Night
For 7 Nights £18,388
8 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
£2,531/Night
For 7 Nights £17,715
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£2,358/Night
For 7 Nights £16,506
6000 ft²
24 Guests
10 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
£2,265/Night
For 7 Nights £15,855
7997.59 ft²
32 Guests
1 Bedroom
13 Bathrooms
Free Cancellation
Villa
- Private Pool
- Spa
- Fireplace/Heating
£2,258/Night
For 7 Nights £15,807
30 Guests
11 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
£2,174/Night
For 7 Nights £15,219
Windham County Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£114/Night
For 7 Nights £796
2303.48 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
£351/Night
For 7 Nights £2,453
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£546/Night
For 7 Nights £3,821
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Balcony/Terrace
- Pet Friendly
- Kitchen
£148/Night
For 7 Nights £1,039
1302.43 ft²
8 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
£169/Night
For 7 Nights £1,184
456 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£222/Night
For 7 Nights £1,557
4 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£171/Night
For 7 Nights £1,201
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£107/Night
For 7 Nights £750
Windham County Large Vacation Homes
10 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
£273/Night
For 7 Nights £1,909
2798.62 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
£502/Night
For 7 Nights £3,517
30 Guests
9 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
£1,109/Night
For 7 Nights £7,760
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Spa
- Skiing
£188/Night
For 7 Nights £1,318
1593.06 ft²
8 Guests
5 Bedrooms
3 Bathrooms
Ski Chalet
- Skiing
- Fireplace/Heating
- Balcony/Terrace
£370/Night
For 7 Nights £2,587
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Skiing
£469/Night
For 7 Nights £3,285
2980 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
£464/Night
For 7 Nights £3,246
3000 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
£294/Night
For 7 Nights £2,055
Why Choose Rent By Owner for your Windham County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windham County
When should you plan your Vacation Rentals stay?
Knowing the best time to visit here can enhance your experience, allowing you to enjoy the region's natural beauty and seasonal activities at their peak.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather ideal for outdoor activities and exploring scenic landscapes within Windham County. It's a popular time for families and adventurers seeking a relaxing retreat.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to October)
Autumn offers vibrant foliage and crisp air, making it an excellent season to enjoy the region's natural beauty during your stay. The area is especially popular among travelers looking to experience colorful landscapes.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Spring (April to May)
In spring, the area begins to awaken with blooming flora and milder temperatures, providing a peaceful setting for those seeking fewer crowds and a more relaxed pace in this part of Vermont.
Average Temperature Daytime: 50°F to 65°F - Nighttime: 30°F to 45°F
Winter (December to February)
Winter transforms the region into a snowy wonderland, attracting visitors interested in winter sports and cozy stays. This quieter period offers a serene environment away from peak crowds.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
Weekly Weather Forecast for Windham County
How to Book Your Windham County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windham County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a spacious patio or deck ideal for relaxing or entertaining.
- Benefit from access to scenic hiking trails, perfect for exploring the natural beauty of the area.
- Take advantage of well-maintained gardens and landscaped yards that enhance your outdoor experience.
- Make use of outdoor grilling amenities to enjoy meals al fresco with family or friends.
- Experience the convenience of nearby swimming pools or hot tubs for ultimate relaxation.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Explore the region's outdoor sports facilities, including tennis courts or golf courses, within easy reach.
Top Attractions Around Windham County
What attractions are nearby?
While staying in this charming region, you can enjoy a variety of outdoor activities such as hiking, biking, and exploring scenic trails that showcase the area's natural beauty.
Family Activities
- Hiking at Windham County’s Local Trails: Explore the region’s scenic trails perfect for family hikes, offering stunning views and an opportunity to enjoy the natural beauty of Vermont.
- Visiting Local Farms and Markets: Experience farm-fresh products and educational tours that provide a fun and engaging way for your family to learn about Vermont’s agricultural heritage.
- Exploring Cultural Events and Festivals: Participate in seasonal festivals and community events held throughout the region, perfect for creating memorable family moments in this area.
- Enjoying Outdoor Recreation Activities: Take advantage of lakes, parks, and outdoor sports facilities nearby to enjoy swimming, fishing, or picnicking with loved ones in this welcoming destination.
Adult Activities
- Hiking and Nature Walks: Discover scenic trails through lush forests and rolling hills, allowing you to enjoy the natural beauty of this region firsthand.
- Local Art Galleries and Studios: Explore the vibrant arts scene with visits to galleries showcasing regional artists, offering a unique cultural experience.
- Wine Tasting Tours: Experience tastings at nearby wineries where you can savor local wines amidst picturesque vineyard views.
- Shopping in Charming Towns: Browse independent shops and boutiques in the area’s quaint towns for handcrafted goods and souvenirs.
Other Places to Stay in Windham County, VT
West Dover
Mount Snow Valley
Wilmington
West Halifax
Jamaica
Putney
Halifax
Wardsboro
Brattleboro
Stratton
South Londonderry
Whitingham
Windham County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area's scenic trails and natural landscapes to enjoy hiking, biking, or exploring during your stay.
- Visit seasonal events and festivals: Check out local calendars to partake in community events that showcase the region's unique culture and traditions.
- Plan for year-round dining experiences: Discover the region's farm-to-table restaurants and cozy eateries to savor authentic flavors throughout your visit.
- Utilize local resources for tips: Consult with your hosts or local visitor centers to uncover hidden gems and the best ways to experience this destination fully.
Transportation Options
- Car Rentals: Renting a vehicle provides you with the flexibility to explore Windham County at your own pace and visit its scenic spots conveniently.
- Public Transportation: Local buses serve the area, making it easy to navigate between towns and attractions without the hassle of driving.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber or Lyft are readily available for quick and comfortable transportation within this destination.
- Airport Transfers: Shuttle services and private transfers from nearby airports ensure smooth arrivals and departures in the region.
Local Customs Options
- Local Craftsmanship: The region values traditional craftsmanship, which you can observe in the handmade furniture and artisanal products showcased throughout here.
- Sugar Maple Sugar Shacks: Visiting the sugar shacks during sugaring season offers a unique insight into this sweet local custom rooted in the area's heritage.
- Seasonal Festivals: Participating in seasonal festivals celebrates the area’s vibrant community spirit and outdoor traditions that define this destination.
- Farmers’ Markets: Engaging with local farmers at markets highlights the region's farm-to-table practices and fresh produce that are central to its culture.
Frequently Asked Questions About Windham County?
1. What are the top vacation rentals in Windham County?
There are a lot of options in Windham County. If you plan on staying in the Windham County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windham County:
- Quiet country cottage
- Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
- The Wilmington Inn
- Serenity Cottage in Southern Vermont…
- Grafton Village Haven
- Vikings Villages Resort
- Ski-in-Ski-Out Condo Located on Mount Snow
- 3 BR/2 Bath Post and Beam - Next to Haystack Golf Course.
- Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
- Amazing Luxury 100 Acre Estate 10BRs, Sauna, Hot Tub, Swimming pool, Game House!
2. How many vacation rentals have private pools in Windham County?
There are 71 vacation rentals with private pools near Windham County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windham County are best for families?
If you are looking for a family-friendly vacation home in Windham County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windham County:
4. How many Rentbyowner vacation rentals are available in Windham County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1939 in the Windham County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windham County.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so it’s recommended to review the specific terms on the property page or contact the owner directly for detailed information.
6. How do I know if my booking for a vacation rental in the region is secure?
Bookings are secured through a trusted platform that ensures your payment and personal information are protected. Confirm the security measures on the listing or consult with the host if you have concerns.
7. Are there any additional fees when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes may apply depending on the property. Always review the full pricing details on the listing before finalizing your reservation.
8. What amenities can I expect in vacation rentals around here?
Amenities vary across properties but typically include essentials and sometimes extras like Wi-Fi, parking, or outdoor spaces. Check the property description for a comprehensive list of what’s offered.
9. How can I communicate special requests or questions about my stay in these vacation rentals?
You can reach out directly to the property owner or manager through the messaging feature on the booking platform to discuss any special requests or clarify details about your stay.
Windham County Top Rated Vacation Rentals
3000 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
£298/Night
For 7 Nights £2,086
1450 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Skiing
£647/Night
For 7 Nights £4,529
1450 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Skiing
£647/Night
For 7 Nights £4,529
7000 ft²
27 Guests
10 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
£2,167/Night
For 7 Nights £15,167
4000 ft²
18 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
£546/Night
For 7 Nights £3,823
7250 ft²
18 Guests
9 Bedrooms
7 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
£1,317/Night
For 7 Nights £9,222
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
£110/Night
For 7 Nights £768
2040 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
£363/Night
For 7 Nights £2,539
