Winchester Cottage Rentals & Holiday Homes

Frequently Asked Questions About Winchester Rental Cottages

What are the top rated Cottage 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 Cottage Rentals in Winchester:

• Enduring Heart Bed and Breakfast Inc.
• 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
• Country church converted into comfy, elegant escape — outdoor entertainment area
• RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
• M’s Studio - Private Modern Luxury Apartment (close to Calypso Waterpark)
• Inviting 1 Bedroom Fully Furnished smoke-free Guest House
• The Wabi Sabi 4-bedrooms Designer Home
• Rideau River Getaway

How much does it cost to rent a cottage in Winchester?

The average cost for a cottage rental in Winchester is $246 per night. Vacation Cottage has a wide list of great cottages near Winchester that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winchester that allow pets?

Yes, here are the top cottage rentals in Winchester that allow you to bring your pet:

• Rideau River Retreat - Waterfront Home
• Doran Bay Resort
• Hot Tub | Dock | Swimming | Close To Ottawa
• Pet friendly Cottage on World Heritage Rideau River
• L'est Ontarien à son Meilleur!
• The Wabi Sabi 4-bedrooms Designer Home
• Enduring Heart Bed and Breakfast Inc.
• RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

See all pet-friendly vacation rentals in Winchester on Vacation Cottage

Do you have any rental cottages in Winchester that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winchester to find one that works for you.

Are there quality cottages in Winchester that have indoor swimming pools?

As of 2025, the data from Vacation Cottage shows that there are Over 7 private swimming pools or cottages with indoor pools in the Winchester area along with other great amenities.

Do any cottages in Winchester have hot tubs?

About 7 cottages in Winchester boast of premium hot tubs. Some of the popular places to stay with hot tubs include:

• Winchester rentals with hot tub

Are there luxury cottages in Winchester?

Yes, there are luxury cottages in Winchester. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winchester.