Best Vacation Homes in Windham
Cabin
10.0(165 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R3,764/Night
7 Nights - R26,351
House
10.0(2 Reviews)
1 Bedroom
3 Baths
8 Guests
3261.46 ft²
Hot Tub
Skiing- Fireplace/Heating
- Balcony/Terrace
R11,952/Night
7 Nights - R83,668
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
Internet
Child Friendly
R3,560/Night
7 Nights - R24,917
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
922 ft²
- Skiing
- Fireplace/Heating
- Kitchen
Parking
R5,170/Night
7 Nights - R36,190
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1614.59 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
R6,086/Night
7 Nights - R42,600
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Skiing
- Fireplace/Heating
- Kitchen
- Parking
R4,452/Night
7 Nights - R31,163
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R3,758/Night
7 Nights - R26,302
Cabin
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Kitchen
- Internet
- Child Friendly
Security/Safety
R7,383/Night
7 Nights - R51,681
Windham Luxury Rentals
House
10.0(57 Reviews)
11 Bedrooms
6 Baths
30 Guests
Private Pool- Hot Tub
Spa- Skiing
R49,071/Night
7 Nights - R343,504
House
9.2(45 Reviews)
8 Bedrooms
4 Baths
15 Guests
6144 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R23,017/Night
7 Nights - R161,123
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
15 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R16,740/Night
7 Nights - R117,188
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R14,977/Night
7 Nights - R104,844
House
4 Bedrooms
3 Baths
15 Guests
3498.27 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Kitchen
R14,283/Night
7 Nights - R99,983
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
3263 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R11,337/Night
7 Nights - R79,350
House
7 Bedrooms
3 Baths
10 Guests
4300 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
R9,963/Night
7 Nights - R69,742
House
5 Bedrooms
3 Baths
10 Guests
2848 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,349/Night
7 Nights - R58,437
Windham Pet Friendly Vacation Rentals
Ski Chalet
10.0(45 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,877/Night
7 Nights - R27,142
Hotel
7.8(139 Reviews)
3 Baths
247.57 ft²
Oceanfront- Skiing
- Fireplace/Heating
Pool
R1,917/Night
7 Nights - R13,415
House
10.0(22 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,296/Night
7 Nights - R51,071
Ski Chalet
10.0(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R7,387/Night
7 Nights - R51,714
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
2500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R6,529/Night
7 Nights - R45,698
Ski Chalet
10.0(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,883/Night
7 Nights - R34,179
House
9.6(5 Reviews)
4 Bedrooms
1 Bath
12 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
R3,873/Night
7 Nights - R27,109
House
9.0(4 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R6,230/Night
7 Nights - R43,605
Windham Large Vacation Homes
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,704/Night
7 Nights - R46,934
House
10.0(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R7,014/Night
7 Nights - R49,093
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
R7,855/Night
7 Nights - R54,977
House
10.0(29 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,337/Night
7 Nights - R44,364
House
10.0(21 Reviews)
5 Bedrooms
5 Baths
8 Guests
3431 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R9,843/Night
7 Nights - R68,902
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Skiing
- Fireplace/Heating
- Pet Friendly
- Kitchen
R11,360/Night
7 Nights - R79,515
Cabin
10.0(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
2900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,306/Night
7 Nights - R37,145
House
4 Bedrooms
3 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R8,748/Night
7 Nights - R61,239
Why Choose Rent By Owner for your Windham 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
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation here ensures you experience the region’s natural beauty and outdoor activities at their best, making your stay in Windham, Vermont, USA truly memorable and enjoyable.
Peak Season Highlights
Winter (December to February)
During the peak winter months, this area transforms into a popular destination for snow sports enthusiasts seeking a scenic escape in Vermont.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 10°F
Fall (September to November)
Autumn draws many travelers with its vibrant foliage and crisp air, making it an ideal time to enjoy the natural beauty of the region.
Average Temperature Daytime: 50°F to 65°F - Nighttime: 30°F to 45°F
Off-Season Highlights
Spring (March to May)
In early spring, the quiet countryside offers a peaceful retreat before the busy summer season begins in this scenic destination.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 25°F to 40°F
Summer (June to August)
Lighter crowds and pleasant weather make summer a favorable time to explore outdoor activities and enjoy the lush landscape here.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Weekly Weather Forecast for Windham
How to Book Your Windham 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
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 outdoor dining with a private BBQ grill, perfect for savoring meals amidst scenic surroundings.
- Take advantage of a spacious patio or deck area to relax and soak in the regional views.
- Benefit from well-maintained garden spaces where you can unwind amid native flora.
- Make use of convenient on-site parking facilities for easy access during your stay.
- Experience scenic walking or hiking trails accessible directly from the property, ideal for exploring the area's natural beauty.
- Utilize the available outdoor fire pit for cozy evenings under the stars.
- Access to outdoor sports facilities such as tennis courts or volleyball areas often found in this destination’s rental properties.
Top Attractions Around Windham
What attractions are nearby?
During your stay, you'll have the opportunity to enjoy outdoor activities such as hiking and skiing in this region, making it an ideal destination for adventure seekers and nature lovers alike.
Family Activities
- Windham Hill Inn & Trails: Explore family-friendly trails for hiking and biking, offering scenic views that make outdoor adventures in this region memorable for all ages.
- Windham Mountain Resort: Enjoy a variety of winter activities like skiing and snowboarding, perfect for creating fun-filled family days on the slopes close to your rental here.
- Windham County Fairgrounds: Attend seasonal fairs and community events, providing engaging entertainment and local culture experiences suitable for children and adults alike.
- Local Nature Centers and Parks: Discover open spaces and nature centers where you can picnic, observe wildlife, and participate in educational programs right in this area.
Adult Activities
- Skiing and Snowboarding: Take advantage of the area’s renowned slopes during winter for exhilarating skiing and snowboarding experiences amidst stunning mountain scenery.
- Hiking and Nature Trails: Explore scenic hiking trails that wind through the region’s lush forests, offering a peaceful escape and breathtaking views for outdoor enthusiasts.
- Local Art Galleries and Studios: Discover vibrant art scenes by visiting local galleries and studios showcasing works inspired by the area's natural beauty and cultural heritage.
- Golfing at Scenic Courses: Play a round on picturesque golf courses that provide both a relaxing activity and panoramic vistas of the surrounding landscape.
Windham Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region’s natural beauty by planning hiking, biking, or skiing adventures right from your Windham vacation rental.
- Discover seasonal events: Check out the area’s calendar for festivals and community events that will enrich your stay and give you a taste of local culture.
- Plan ahead for dining experiences: While here, explore nearby eateries and consider booking reservations in advance to enjoy the region’s best culinary offerings.
- Utilize local resources: Reach out to local visitor centers or hosts for personalized tips on hidden gems and must-see sights during your stay.
Transportation Options
- Windham County Transit Service: Provides reliable bus transportation across the area, making it easy to explore this scenic destination without the need for a car.
- Regional Airport (Rutland Southern Vermont Regional Airport): Offers convenient flights from major cities, connecting you effortlessly to the region for a comfortable arrival or departure.
- Taxi Services and Ridesharing: Local taxis and rideshare options like Uber are readily available here, providing flexible transportation around this peaceful spot in Vermont.
- Car Rental Agencies: Numerous rental companies operate nearby, giving you the freedom to explore the region's natural beauty at your own pace with a rental vehicle.
Local Customs Options
- Welcoming Community Spirit: Residents here take pride in their friendly and inclusive attitude, making newcomers feel like part of the local area from the moment they arrive.
- Respect for Nature: The region values environmental preservation, encouraging visitors to participate in sustainable practices during their stay.
- Local Food Traditions: Enjoy the region’s culinary customs, which emphasize farm-to-table ingredients and seasonal dishes that reflect the area's agricultural heritage.
- Celebrating Seasonal Festivals: Participate in community events and festivals that highlight the area's rich cultural traditions throughout the year.
Frequently Asked Questions About Windham?
1. What are the top vacation rentals in Windham?
There are a lot of options in Windham. If you plan on staying in the Windham 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:
- Private secluded trout cabin- sleeps 2
- Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
- Mountain chalet
- Maple Season Basecamp: 3 mi to Magic, Paved Road Access
- Londonderry Chalet w/Deck, Fire Pit & Views!
- Cozy Ski-In/Ski-Out Condo on Magic Mountain
- New! Cozy, private Chalet with stunning Mountain Views.
- Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing
- Beautiful house w/mountain & pond views, hot tub, pool table, bbq, firepit, w/d
- Family-sized Farmhouse w/deck & access to private Vermont Quarry. Pet Friendly!
2. Which vacation homes in Windham are best for families?
If you are looking for a family-friendly vacation home in Windham, 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:
3. How many Rentbyowner vacation rentals are available in Windham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 77 in the Windham 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.
4. What is the cancellation policy for vacation rentals in Windham, Vermont?
Cancellation policies vary by listing, so it’s important to review the specific terms on each property’s page. Some rentals may offer flexible cancellation options, while others may have stricter policies. Contact the owner directly if you need clarification.
5. How do I find the best vacation rental deals in Windham, Vermont?
To secure the best deals, compare listings based on price, amenities, and reviews. Booking early and checking for special offers or discounts can also help you find more affordable options here. Detailed descriptions and photos are available to assist your decision.
6. Are pets allowed in vacation rentals in Windham, Vermont?
Pet policies vary among individual rentals, with some properties welcoming animals and others not. Be sure to check the pet policy listed on the property’s page or contact the owner to confirm if traveling with your pet.
7. What amenities should I expect from vacation rentals in Windham, Vermont?
Amenities differ between properties but often include essentials like Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. Review each listing carefully to ensure it meets your needs before booking.
8. How do I communicate with hosts for vacation rentals in Windham, Vermont?
Most listings provide a messaging platform or contact details to reach out directly to owners. Using these channels allows you to ask questions about the property, clarify policies, or request additional information before confirming your reservation.
Windham Top Rated Vacation Rentals
Bed & Breakfast
9.2(118 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R2,647/Night
7 Nights - R18,523
Hotel
8.2(700 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R2,034/Night
7 Nights - R14,239
House
10.0(1 Review)
4 Bedrooms
4 Baths
10 Guests
3253 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R6,327/Night
7 Nights - R44,298
House
4 Bedrooms
3 Baths
8 Guests
3900 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R19,739/Night
7 Nights - R138,183
Condo
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
R1,922/Night
7 Nights - R13,447
