Best Vacation Homes in Winchester
Condo
10.0(12 Reviews)
2 Bedrooms
1 Bath
8 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $145/Night
7 Nights - US $1,013
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
9 Guests
2734.03 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $624/Night
7 Nights - US $4,366
Bed & Breakfast
9.6(115 Reviews)
1 Bedroom
1 Bath
Spa- Balcony/Terrace
Breakfast- Parking
US $103/Night
7 Nights - US $723
Apartment
10.0(6 Reviews)
1 Bedroom
2 Baths
3 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $112/Night
7 Nights - US $784
Bed & Breakfast
9.0(102 Reviews)
4 Bedrooms
1 Bath
10 Guests
118.4 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Breakfast
US $92/Night
7 Nights - US $642
House
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $92/Night
7 Nights - US $645
House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $155/Night
7 Nights - US $1,082
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
US $135/Night
7 Nights - US $947
Winchester Luxury Rentals
House
10.0(1 Review)
5 Bedrooms
3 Baths
11 Guests
3031 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $643/Night
7 Nights - US $4,499
Cottage
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $598/Night
7 Nights - US $4,185
House
10.0(8 Reviews)
4 Bedrooms
2 Baths
9 Guests
2733 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $558/Night
7 Nights - US $3,908
House
4 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $355/Night
7 Nights - US $2,484
House
4 Bedrooms
2 Baths
8 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $350/Night
7 Nights - US $2,452
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $317/Night
7 Nights - US $2,217
Villa
10.0(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
3600 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $287/Night
7 Nights - US $2,011
House
9.0(2 Reviews)
1 Bedroom
3 Baths
9 Guests
10763.91 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,008
Winchester Pet Friendly Vacation Rentals
Apartment
8.8(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $92/Night
7 Nights - US $644
Ski Chalet
7.6(103 Reviews)
9 Bedrooms
9 Baths
37 Guests
4245.77 ft²
Oceanfront- Fireplace/Heating
- Pool
Ocean View
US $87/Night
7 Nights - US $607
Boat Rental
9.8(12 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $170/Night
7 Nights - US $1,191
Hotel
8.6(27 Reviews)
6 Baths
525.64 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $275/Night
7 Nights - US $1,928
Cottage
10.0(6 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $393/Night
7 Nights - US $2,749
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $148/Night
7 Nights - US $1,034
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $313/Night
7 Nights - US $2,192
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $262/Night
7 Nights - US $1,836
Winchester Large Vacation Homes
Cabin
10.0(16 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $269/Night
7 Nights - US $1,881
House
8.0(1 Review)
34 Bedrooms
30 Baths
89 Guests
952.6 ft²
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $102/Night
7 Nights - US $714
New
House
5 Bedrooms
5 Baths
10 Guests
3500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $170/Night
7 Nights - US $1,191
House
4 Bedrooms
4 Baths
10 Guests
5382 ft²
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $234/Night
7 Nights - US $1,640
Why Choose Rent By Owner for your Winchester 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 Winchester
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the local shoulder seasons when the region experiences pleasant weather and fewer crowds, ensuring an authentic and comfortable experience in Winchester and its surrounding areas.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can enjoy warm weather and longer daylight hours, ideal for exploring the area's outdoor activities and scenic landscapes.
Average Temperature Daytime: around 25°C - Nighttime: around 15°C
Fall (September to October)
This season offers vibrant fall foliage and pleasant temperatures, making it a perfect time to experience the region's natural beauty without the summer crowds.
Average Temperature Daytime: around 20°C - Nighttime: around 10°C
Off-Season Highlights
Winter (November to February)
In the winter months, the area becomes quieter, providing a peaceful setting for cozy stays and scenic winter views from your rental property.
Average Temperature Daytime: -5°C - Nighttime: -12°C
Spring (March to May)
Springtime brings milder weather and blooming landscapes, offering a more relaxed atmosphere for your getaway while avoiding the busier seasons.
Average Temperature Daytime: around 10°C - Nighttime: around 2°C
Weekly Weather Forecast for Winchester
How to Book Your Winchester 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 Winchester
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 spaces perfect for family gatherings or romantic dinners under the stars.
- Benefit from spacious yards ideal for children’s play or relaxing afternoons in the sunshine.
- Relax on private patios or decks with scenic views of the surrounding countryside.
- Take advantage of well-maintained gardens that add natural beauty to your stay.
- Make use of convenient outdoor parking facilities for easy access and mobility.
- Utilize outdoor fire pits or barbeque grills for cozy evenings and outdoor cooking experiences.
- Explore nearby walking or biking trails that showcase the region's picturesque landscape.
Top Attractions Around Winchester
What attractions are nearby?
While staying here, you can explore a variety of outdoor activities and local attractions nearby that showcase the natural beauty and cultural charm of Winchester and its surrounding region in North Dundas, Ontario.
Family Activities
- Winchester & Heritage Museum: Dive into local history and enjoy interactive exhibits that are perfect for family outings in this charming Ontario town.
- North Dundas Community Centre: Participate in family-friendly activities, sports, and recreational programs designed to keep all ages entertained during your visit.
- Patrimoine Winery Tour: Explore the scenic vineyards on a family-appropriate tour, offering a taste of the region’s renowned wine culture amidst beautiful countryside.
- Local Parks and Trails: Discover the region's natural beauty by walking or biking along scenic trails and relaxing at parks ideal for picnics and outdoor fun with the family.
Adult Activities
- Winchester Golf & Country Club: Enjoy a relaxing day on the scenic fairways, perfect for golf enthusiasts seeking leisure near your vacation rental.
- Winchester Public Library: Discover local history and culture through engaging exhibits and community events just a short drive from here.
- North Dundas Trails: Explore peaceful walking and biking paths that wind through the region’s picturesque countryside, ideal for outdoor adventures.
- Local Wineries: Sample regional wines and enjoy tastings at nearby wineries, offering a refined experience within easy reach of your stay.
Other Places to Stay in Winchester, ON
North Dundas
Winchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of nearby natural parks and cultural sites to enrich your stay and experience the area's unique charm.
- Plan Your Meals Ahead: Discover local dining options or stock up at nearby markets to enjoy authentic regional cuisine during your visit.
- Check Seasonal Events: Align your trip with seasonal festivals or community events to immerse yourself in the local festivities and traditions.
- Utilize Nearby Transportation: Use available transit options or rental services to easily navigate between your vacation rental and the region’s key attractions.
Transportation Options
- Winchester Transit Bus Service: This local bus system offers convenient and affordable transportation options within the area, making it easy to explore nearby attractions and amenities.
- Rental Cars: Several rental car agencies operate in this region, providing flexible mobility options for longer excursions or day trips around North Dundas and beyond.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps like Uber are available here, offering quick and reliable transportation directly to your vacation rental or other destinations.
- Cycling and Walking Paths: The area features scenic routes perfect for cycling or strolling, allowing you to enjoy the natural beauty while getting around conveniently.
Local Customs Options
- Traditional Local Festivals: Participating in the area's seasonal festivals offers a glimpse into the community’s history and cultural pride, enriching your stay in this destination.
- Respect for Agricultural Practices: The region values its farming heritage, and visitors are encouraged to observe local customs related to agricultural events and markets with respect.
- Community Gatherings and Events: Engaging in neighborhood gatherings fosters a sense of connection and provides authentic experiences unique to this part of Ontario.
- Hospitality and Courtesy: Showing politeness and courteous behavior aligns with the region’s friendly atmosphere, making your interactions with locals more meaningful during your stay.
Winchester Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winchester:
- Meet our adorable alpaca herd , & stay in our luxury Cabin overlooking the farm
- L'est Ontarien à son Meilleur!
- The Wabi Sabi: 4-bedrooms designer home
- M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
- Inviting 1 Bedroom Fully Furnished smoke-free Guest House
- Modern Comfort + Private View. 30 mins to Ottawa downtown and Airport.
- Country church converted into comfy, elegant escape — outdoor entertainment area
- Stunning Home close to Ottawa
- The Wabi Sabi 4-bedrooms designer home
- Cozy River Home
2. Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
3. How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 77 in the Winchester 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 Winchester.
4. What is the cancellation policy for vacation rentals in Winchester, North Dundas?
The cancellation policy varies depending on the property listed. To ensure you understand the terms, please review the specific listing details or contact the property owner directly before confirming your booking.
5. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, service charges, or security deposits are often detailed in the listing. It’s recommended to read the full description and reach out to the owner if you have questions about extra costs.
6. How do I verify the amenities included in my chosen vacation rental in North Dundas?
Amenities are specified in each listing; however, if you need clarification or specific requirements, contacting the property owner will ensure you have all the necessary details prior to booking.
7. What is the check-in and check-out process for vacation rentals here?
Check-in and check-out procedures are outlined in the listing details. For any special requests or questions about the process, it’s best to communicate directly with the property owner.
8. Is there a minimum stay requirement for booking vacation rentals in this region?
Minimum stay policies vary between properties. Please review the individual listing or contact the owner to confirm the length of stay needed for your travel dates.
Winchester Top Rated Vacation Rentals
Hotel
8.4(473 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
US $147/Night
7 Nights - US $1,030
Hotel
8.2(166 Reviews)
5 Baths
266.94 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $134/Night
7 Nights - US $938
Cottage
7.8(21 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $151/Night
7 Nights - US $1,057
Bed & Breakfast
10.0(27 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
US $196/Night
7 Nights - US $1,374
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $191/Night
7 Nights - US $1,339
US $526/Night
7 Nights - US $3,679
