Best Vacation Homes in Windsor
House
10.0(76 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R3,777/Night
7 Nights - R26,450
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1948.27 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Internet
R8,350/Night
7 Nights - R58,454
Resort
9.0(830 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Air Conditioner
Child Friendly
R3,389/Night
7 Nights - R23,731
Cabin
10.0(64 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,138/Night
7 Nights - R21,968
House
10.0(1 Review)
4 Bedrooms
4 Baths
9 Guests
3465.98 ft²
Hot Tub- Fireplace/Heating
- Parking
- Internet
R15,035/Night
7 Nights - R105,240
Condo
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Hot Tub
Skiing- Fireplace/Heating
Pool
R3,871/Night
7 Nights - R27,093
Cabin
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
520 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,426/Night
7 Nights - R37,986
Cabin
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
520 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,639/Night
7 Nights - R39,469
Windsor Luxury Rentals
House
16 Bedrooms
19 Baths
39 Guests
- Internet
- Child Friendly
Security/Safety
R65,379/Night
7 Nights - R457,643
House
8.0(2 Reviews)
4 Bedrooms
3 Baths
9 Guests
3464 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R13,377/Night
7 Nights - R93,638
House
10.0(1 Review)
5 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R9,948/Night
7 Nights - R69,644
House
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,675/Night
7 Nights - R60,728
Cabin
4 Bedrooms
2 Baths
7 Guests
1532 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R8,509/Night
7 Nights - R59,558
House
9.8(42 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,029/Night
7 Nights - R56,196
House
10.0(21 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R7,859/Night
7 Nights - R55,009
Cabin
9.8(98 Reviews)
4 Bedrooms
4 Baths
14 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R7,314/Night
7 Nights - R51,203
Windsor Pet Friendly Vacation Rentals
Cabin
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
520 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,562/Night
7 Nights - R38,942
Cabin
2 Bedrooms
1 Bath
4 Guests
520 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,655/Night
7 Nights - R39,584
Cabin
2 Bedrooms
1 Bath
4 Guests
520 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,546/Night
7 Nights - R38,826
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
1950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,914/Night
7 Nights - R48,401
House
8.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
R6,528/Night
7 Nights - R45,698
Cabin
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,892/Night
7 Nights - R34,245
House
10.0(30 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,238/Night
7 Nights - R43,671
Condo
9.6(12 Reviews)
3 Bedrooms
2 Baths
8 Guests
1350 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,703/Night
7 Nights - R39,914
Windsor Large Vacation Homes
Villa
9.6(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,981/Night
7 Nights - R27,867
Villa
9.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,575/Night
7 Nights - R25,033
Villa
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R4,221/Night
7 Nights - R29,548
Villa
9.6(17 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R4,922/Night
7 Nights - R34,459
Condo
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,845/Night
7 Nights - R33,915
House
10.0(1 Review)
15 Bedrooms
15 Baths
32 Guests
14500 ft²
Spa- Fireplace/Heating
Lake View- Balcony/Terrace
R67,567/Night
7 Nights - R472,969
Villa
3 Bedrooms
3 Baths
7 Guests
- Air Conditioner
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
R8,652/Night
7 Nights - R60,563
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,312/Night
7 Nights - R44,182
Why Choose Rent By Owner for your Windsor 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 Windsor
When should you plan your Vacation Rentals stay?
Timing your visit to this charming area can enhance your experience, as the region offers unique attractions and natural beauty throughout different seasons, making it essential to choose the right time for a memorable stay.
Peak Season Highlights
Summer (June to August)
Experience the warmest weather and vibrant outdoor activities in the region during these months, making it an ideal time for exploring the area's scenic beauty and local events.
Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
Fall (September to November)
Enjoy the stunning fall foliage that transforms the landscape into a tapestry of colors, attracting visitors seeking picturesque views and seasonal festivities.
Average Temperature Daytime: 60°F - 70°F - Nighttime: 40°F - 50°F
Off-Season Highlights
Winter (December to February)
During this period, the area offers a peaceful retreat with crisp air and snow-covered scenery, perfect for cozying up indoors or enjoying winter sports nearby.
Average Temperature Daytime: 25°F - 35°F - Nighttime: 10°F - 20°F
Early Spring (March to April)
As winter transitions to spring, you can experience fewer crowds while witnessing the first signs of nature's renewal in this picturesque destination.
Average Temperature Daytime: 45°F - 55°F - Nighttime: 30°F - 40°F
Weekly Weather Forecast for Windsor
How to Book Your Windsor 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 Windsor
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 patio or deck to relax and dine amidst scenic views.
- Take advantage of well-maintained gardens or landscaped yards for outdoor leisure.
- Make use of a barbecue grill to host cookouts in the fresh air.
- Discover nearby hiking trails or nature paths accessible from your rental.
- Utilize outdoor seating areas perfect for morning coffee or evening gatherings.
- Access to spacious lawns ideal for outdoor games and activities.
- Benefit from outdoor fire pits for cozy evenings under the stars.
Top Attractions Around Windsor
What attractions are nearby?
Enjoy a variety of outdoor activities and local attractions just moments from your vacation rentals, offering you the perfect opportunity to explore the scenic beauty and charming culture of this destination.
Family Activities
- Windsor County Fairgrounds: Experience family-friendly events and outdoor activities that offer a glimpse into local traditions and community spirit in the region.
- Vermont Institute of Natural Science (VINS): Discover wildlife exhibits and nature trails perfect for engaging children and teaching them about the area's rich natural environment.
- Downtown Windsor Historic District: Stroll through this charming district to enjoy boutique shops, historic architecture, and casual dining options suitable for all ages.
- Local Parks and Recreation Areas: Relax and play at scenic parks with picnic areas, playgrounds, and walking paths nestled within the region’s lush landscapes.
Adult Activities
- Windsor County Scenic Drive: Embark on a picturesque journey through the area's stunning landscapes, perfect for a relaxing day of sightseeing and appreciating Vermont's natural beauty.
- The Vermont History Museum: Delve into the region's rich history and cultural heritage, offering an engaging experience that connects you with the local story.
- Vermont Pub & Brewery Tour: Enjoy exploring some of the region’s renowned craft breweries, tasting locally brewed beers in a vibrant and welcoming atmosphere.
- Golfing at the Windsor Golf Course: Take advantage of the region's well-maintained golf courses, ideal for a leisurely round amid scenic surroundings.
Other Places to Stay in Windsor, VT
Path of Life Garden
Harpoon Brewery
Mt Ascutney Hospital and Health Center: Primary Care - Windsor
The Sustainable Farmer
Paradise Park
Brownsville Trail
South Congregational Church
American Precision Museum
Old Constitution House
Ascutney
Mount Ascutney
Mt Ascutney State Park
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore local attractions nearby: Take advantage of the region’s scenic beauty by visiting outdoor spots that showcase the area's natural charm, making your stay truly memorable.
- Plan your dining experiences: Savor the best of local cuisine at nearby eateries to enjoy authentic flavors and support the area's vibrant culinary scene.
- Check out seasonal events: Align your visit with local festivals or markets to immerse yourself in the regional culture and make lasting connections.
- Customize your accommodations: Choose vacation rentals that provide personalized amenities to enhance your comfort and ensure a relaxing stay in this destination.
Transportation Options
- Windsor Transit Services: Local bus options provide affordable and convenient transportation throughout the area, making it easy for you to explore without the need for a car.
- Amtrak Vermont Rail: The nearby rail station connects this destination to major cities, offering a scenic and comfortable way to arrive or depart from your vacation rental here.
- Rental Car Services: Several car rental agencies operate in the region, giving you the flexibility to discover Windsor and its surrounding attractions at your own pace.
- Taxis and Ride-Sharing: Taxis and ride-sharing services are readily available, providing quick and reliable transportation options during your stay in this destination.
Local Customs Options
- Local Craftsmanship: You will notice a deep appreciation for traditional Vermont craftsmanship reflected in the area's handcrafted goods and artisanal products.
- Farmers’ Market Traditions: Visiting local farmers' markets offers insight into the region’s agricultural customs and fresh produce that are cherished here.
- Seasonal Festivals: Participating in seasonal festivals allows you to experience the vibrant community spirit and time-honored celebrations of this destination.
- Respect for Nature: The community here emphasizes environmental preservation and outdoor etiquette, integral to enjoying the scenic landscapes in the area.
Frequently Asked Questions About Windsor?
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:
- Meadow View- 35 Acres outside your door
- Sunset Cabin - your private romantic hideaway
- Long Range Mountain Views in West Windsor
- Inviting Vermont Home On Mount Ascutney!
- Snapdragon Inn
- Antique farmhouse with spectacular mountain view in a bucolic setting.
- Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
- Inviting Vermont Home On Mount Ascutney!
- Villa Near Biking and Hiking Trails
2. Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
3. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 72 in the Windsor 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 Windsor.
4. What is the cancellation policy for vacation rentals in Windsor, Vermont?
Cancellation policies vary depending on the property listing. You should review the specific rental’s terms before booking or contact the owner for detailed information about cancellations and potential refunds.
5. How can I ensure my reservation in Windsor, Vermont, is secure?
Reservations are typically secured through the booking platform with secure payment options. It’s advisable to read the host’s safety guidelines and verify their contact information to ensure a smooth experience.
6. Are there any additional fees associated with booking here?
Additional fees such as cleaning, service charges, or taxes are usually specified in the listing details. Always check the full breakdown of costs before finalizing your booking to avoid surprises.
7. What amenities are included in Windsor, Vermont, vacation rentals?
Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, and parking. Review the property description carefully or contact the owner directly to confirm the amenities available during your stay.
8. Is there a minimum stay requirement for booking a vacation rental here?
Minimum stay requirements can differ among listings. Be sure to read the booking details or reach out to the property owner to understand any restrictions or special conditions for your desired dates.
Windsor Top Rated Vacation Rentals
Cottage
9.6(84 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R3,464/Night
7 Nights - R24,242
Resort
8.8(211 Reviews)
7 Baths
47 Guests
991.82 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,307/Night
7 Nights - R16,150
Condo
6.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
969 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
R5,383/Night
7 Nights - R37,689
House
1 Bedroom
1 Bath
4 Guests
699.65 ft²
- Private Pool
- Hot Tub
- Spa
- Skiing
R3,543/Night
7 Nights - R24,802
House
3 Bedrooms
1 Bath
7 Guests
2000 ft²
- Spa
- Fireplace/Heating
- Pool
- Lake View
R9,542/Night
7 Nights - R66,793
Condo
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R8,701/Night
7 Nights - R60,909
Condo
2 Bedrooms
2 Baths
6 Guests
969 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
R7,737/Night
7 Nights - R54,169
Condo
1 Bedroom
1 Bath
4 Guests
699 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Pool
R6,402/Night
7 Nights - R44,825
