Find the best cottages in Winchester - We found 19 exact matches
About Winchester Cottage Rentals on Vacation Cottage
For travelers seeking a comfortable and luxurious retreat in Winchester, Vacation Cottage has you covered. Opt for a cottage rental, lake house retreat, or summer home resort and enjoy the flexibility of a hotel. With over 19 options available in Winchester on Vacation Cottage, we can assist you in finding the perfect accommodation.
Elevate your next vacation with a picturesque cottage rental in Winchester, offering top-notch amenities such as swimming pools, fitness centers, Wi-Fi, luxury suites, and fully-equipped kitchens. Discover unbeatable deals on outdoor vacation cottages, lake houses, and summer home retreats. Start planning your trip to Winchester today and secure your accommodation in minutes on our website.
Whether it's a short-term getaway or a long-term seasonal stay, find the perfect cottage rental, lake house, or summer home for your favorite travel destinations. Compare options with Vacation Cottage and stay close to nature.
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:
- Spectacular Cottage with Shenandoah River Views
- Country Elegance overlooking the Shenandoah River
- Gorgeous Blue Ridge Mountain and Rolling Farm View
- Historical cottage in the town of Paris
- Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
- Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
- The Vue - Mountain top hot tub overlooking the Shenandoah River
- Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
- Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
- Cozy Escape @ the Shenandoah Cottage
How much does it cost to rent a cottage in Winchester?
The average cost for a cottage rental in Winchester is $333 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:
- Charming 2-bedroom cottage with WiFi, AC in delightful Boyce
- Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!
- "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
- Cozy Escape @ the Shenandoah Cottage
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 19 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 19 cottages in Winchester boast of premium hot tubs. Some of the popular places to stay with hot tubs include:
See all holiday vacation rentals in Winchester on Vacation CottageAre there luxury cottages in Winchester?
Yes, there are luxury cottages in Winchester. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winchester.
