Best Vacation Homes in Windsor County
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $193/Night
For 7 Nights CA $1,354
2497.23 ft²
8 Guests
3 Bedrooms
4 Bathrooms
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,413/Night
For 7 Nights CA $9,894
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
CA $411/Night
For 7 Nights CA $2,878
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $263/Night
For 7 Nights CA $1,840
1657.64 ft²
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Apartment
- Skiing
- Fireplace/Heating
- Pet Friendly
CA $745/Night
For 7 Nights CA $5,212
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $319/Night
For 7 Nights CA $2,235
1400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Ski Chalet
- Spa
- Fireplace/Heating
- Pool
CA $472/Night
For 7 Nights CA $3,304
1700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $405/Night
For 7 Nights CA $2,837
Windsor County Luxury Rentals
2230 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
CA $6,183/Night
For 7 Nights CA $43,284
39 Guests
16 Bedrooms
19 Bathrooms
Group Friendly
House
- Internet
- Child Friendly
- Security/Safety
CA $5,524/Night
For 7 Nights CA $38,671
35000 ft²
46 Guests
18 Bedrooms
13 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $4,964/Night
For 7 Nights CA $34,745
5960 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $4,395/Night
For 7 Nights CA $30,764
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Spa
- Skiing
CA $4,387/Night
For 7 Nights CA $30,711
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
CA $4,282/Night
For 7 Nights CA $29,977
17 Guests
8 Bedrooms
9 Bathrooms
House
- Skiing
- Fireplace/Heating
- Breakfast
CA $4,280/Night
For 7 Nights CA $29,962
1880 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
CA $4,122/Night
For 7 Nights CA $28,852
Windsor County Pet Friendly Vacation Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $257/Night
For 7 Nights CA $1,802
1948.27 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
CA $706/Night
For 7 Nights CA $4,939
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $211/Night
For 7 Nights CA $1,477
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
CA $545/Night
For 7 Nights CA $3,816
1517.71 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
CA $549/Night
For 7 Nights CA $3,841
1200 ft²
8 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $569/Night
For 7 Nights CA $3,985
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $289/Night
For 7 Nights CA $2,019
1400 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $591/Night
For 7 Nights CA $4,137
Windsor County Large Vacation Homes
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
CA $1,284/Night
For 7 Nights CA $8,987
2002.09 ft²
12 Guests
5 Bedrooms
2 Bathrooms
House
- Private Pool
- Skiing
- Fireplace/Heating
CA $696/Night
For 7 Nights CA $4,874
10 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Fireplace/Heating
CA $654/Night
For 7 Nights CA $4,579
2314.24 ft²
15 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
CA $1,544/Night
For 7 Nights CA $10,810
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
CA $326/Night
For 7 Nights CA $2,280
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Skiing
- Fireplace/Heating
CA $2,377/Night
For 7 Nights CA $16,637
12 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Breakfast
- Internet
- Child Friendly
CA $615/Night
For 7 Nights CA $4,303
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
CA $278/Night
For 7 Nights CA $1,944
Why Choose Rent By Owner for your Windsor 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 Windsor County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, as the region offers unique attractions and natural beauty throughout different seasons, making it essential to consider the best period for your ideal getaway in Windsor County, Vermont.
Peak Season Highlights
Summer (June to August)
During the summer months, this region experiences warm weather that is perfect for outdoor activities and exploring nature. You'll enjoy longer daylight hours, making it ideal for daytime adventures.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall Foliage (September to October)
This season offers stunning autumn foliage, attracting visitors who want to experience vibrant colors and scenic views. It’s a popular time for outdoor sightseeing and photography in the area.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Late Fall and Early Winter (November to December)
Come here during late fall and early winter when the crowds decrease, and you can enjoy a quieter atmosphere. The cooler temperatures are perfect for cozy accommodations and seasonal festivities.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Early Spring (March to April)
In early spring, the area begins to awaken from winter dormancy, offering a peaceful retreat with fewer tourists. This is an ideal time if you prefer a tranquil setting and budding nature scenery.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Windsor County
How to Book Your Windsor 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 Windsor 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 outdoor grilling with a private barbecue area to savor meals amidst scenic surroundings.
- Take advantage of spacious yards ideal for picnics, sports, or relaxing in the fresh air.
- Make use of dedicated fire pits for cozy evenings and roasting marshmallows under the stars.
- Explore nearby hiking trails and access outdoor gear storage to enhance your adventure experience.
- Relax on outdoor patios or decks that provide picturesque views of the surrounding landscape.
- Utilize well-maintained parking areas suitable for multiple vehicles, making excursions easy and convenient.
- Cycle along marked paths or bike-friendly routes conveniently accessible from most properties here.
Top Attractions Around Windsor County
What attractions are nearby?
In this charming region, you can explore a variety of outdoor activities, cultural sites, and scenic attractions that make for memorable experiences during your stay.
Family Activities
- Windsor County Historic Sites Tour: Discover the rich history of this area by exploring its renowned historic sites, offering an educational experience for the whole family.
- Vermont Symphony Orchestra Family Concerts: Enjoy inspiring musical performances that bring families together in a welcoming setting within the region’s vibrant arts scene.
- Outdoor Adventures at Mount Ascutney State Park: Embark on scenic hikes or participate in outdoor activities suitable for all ages, making it an ideal spot for family fun in this part of Vermont.
- Local Farmers' Markets Visit: Explore fresh produce and artisanal goods at the area's farmers' markets, perfect for a leisurely family outing to experience local flavors and crafts.
Adult Activities
- Wine Tasting Tours: Discover local vineyards and enjoy tasting sessions that highlight the region's renowned wine culture.
- Cultural and Historical Museums: Immerse yourself in the area's rich history and vibrant arts scene at well-curated museums and galleries.
- Gourmet Dining Experiences: Savor farm-to-table cuisine at top-rated restaurants that showcase regional flavors and culinary craftsmanship.
Other Places to Stay in Windsor County, VT
Ludlow
Bridgewater Corners
West Bridgewater
Cavendish
Woodstock
Quechee
Plymouth
Chester
Chester Depot
Proctorsville
Weston
West Windsor
Windsor County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Outdoor Adventures: Take advantage of the area's natural beauty by scheduling outdoor activities early to enjoy peaceful scenic spots and avoid peak times during your stay.
- Explore Local Cuisine: Savor regional flavors by visiting nearby eateries or preparing meals in your rental to experience the authentic taste of this destination's culinary scene.
- Utilize Nearby Cultural Attractions: Make the most of your visit by exploring local museums, galleries, or historical sites that showcase the rich heritage of this region.
- Choose the Right Vacation Rental: Select a well-located property that offers easy access to the area's key attractions, ensuring a comfortable and convenient stay in this destination.
Transportation Options
- Windsor County Taxi Services: Reliable local taxi options are available for convenient travel around the area and to nearby attractions.
- Regional Bus Lines: This destination is served by regional bus routes that connect you to major cities and transportation hubs within Vermont.
- Rental Car Agencies: Several rental car companies operate here, offering flexible transportation for exploring Windsor County at your own pace.
- Private Shuttle Services: Private shuttles provide comfortable and direct transfers to key locations throughout the region, ideal for ease of travel during your stay.
Local Customs Options
- Strawberry Picking Tradition: Embrace the local custom of strawberry picking during the summer months, a beloved activity that showcases the region's rich agricultural heritage.
- Vermont Maple Syrup Tapping: Participate in the maple sugaring season by observing or joining in the traditional process of tapping sap, an integral part of here’s culinary and cultural identity.
- Farmers' Market Engagement: Support community vendors at farmers' markets by purchasing fresh produce and handcrafted goods, reflecting the area's farm-to-table ethos.
- Seasonal Festivals and Fairs: Attend local events and festivals celebrating seasonal changes and regional history, providing insight into the area's vibrant community spirit.
Frequently Asked Questions About Windsor County?
1. What are the top vacation rentals in Windsor County?
There are a lot of options in Windsor County. If you plan on staying in the Windsor 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 Windsor County:
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Luxurious, Secluded, Ski Chalet, w/Country Decor & Hot Tub Near Okemo
- Charming Log Cabin Apartment in Woodstock Village
- GORGEOUS LAKEFRONT - Autumn Splendor - Private Setting - 5 Mins to Okemo!
- Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"
- Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
- Quiet Vermont Winter Getaway
- "The Crooked House" with A/C and sauna on private wooded lot near Killington
- Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
- 11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
2. How many vacation rentals have private pools in Windsor County?
There are 65 vacation rentals with private pools near Windsor County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor County are best for families?
If you are looking for a family-friendly vacation home in Windsor 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 Windsor County:
4. How many Rentbyowner vacation rentals are available in Windsor County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2140 in the Windsor 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 Windsor County.
5. What is the cancellation policy for vacation rentals in Windsor County, Vermont?
Cancellation policies vary by property, so it’s best to review the specific listing details or contact the property owner directly to understand the terms and potential refund options.
6. How do I secure my reservation at a vacation rental in this region?
Reservations are typically confirmed through a secure booking process on the listing page. Make sure to follow the steps outlined, and reach out to the host if you have any questions about your reservation.
7. Are there any additional fees associated with booking a vacation rental in Windsor County?
Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing details. Review these carefully before confirming your booking or contact the owner for clarification.
8. What amenities can I expect at vacation rentals in this destination?
Amenities vary between properties, but most listings will specify features like Wi-Fi, parking, and kitchen facilities. Check the property description or ask the owner directly to ensure it meets your needs.
9. What should I know about checking in and out of vacation rentals here?
Check-in and check-out times are generally listed in the property details. For early or late arrangements, contact the owner beforehand to confirm or discuss possible options.
Windsor County Top Rated Vacation Rentals
4000 ft²
32 Guests
11 Bedrooms
7 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
CA $1,414/Night
For 7 Nights CA $9,898
2100 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $556/Night
For 7 Nights CA $3,888
3800 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $1,535/Night
For 7 Nights CA $10,743
5000 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Skiing
CA $2,400/Night
For 7 Nights CA $16,798
2000 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
CA $530/Night
For 7 Nights CA $3,707
5000 ft²
22 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Other
- Hot Tub
- Fireplace/Heating
- Pool
CA $1,237/Night
For 7 Nights CA $8,657
1900 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Spa
- Skiing
- Fireplace/Heating
CA $1,790/Night
For 7 Nights CA $12,530
1240 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
CA $843/Night
For 7 Nights CA $5,899
