Discover the 396 Best Resorts in Winchester
About Winchester Cottage Resorts on Vacation Cottage
Looking for accommodations? Numerous resorts offer condos and apartment-style units for reservation. Winchester boasts a variety of nearby resorts, offering plentiful options for travelers. Access over 396 options resorts in the vicinity of Winchester, along with exciting activities to enjoy during your stay.
In the Winchester region, you'll find multiple resorts equipped with amenities such as gyms, WiFi, spas, private pools, and pet-friendly rooms. These resorts cater to various types of travelers: from honeymooners seeking romance to couples planning destination weddings, golf enthusiasts, or those attending conferences and business meetings.
Additionally, all-inclusive resorts in Winchester cater to couples, families, and groups, accommodating both short-term and long-term stays. Vacation Cottage offers a wide array of resorts in or near Winchester, serving as an excellent alternative to traditional vacation rentals and ensuring you discover the perfect lodging for your next trip.
Frequently Asked Questions About Winchester Cottage Resorts
What are the top rated Resort 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 Resort Rentals in Winchester:
- Spectacular Cottage with Shenandoah River Views
- 3 KING Master Suites ~ Dog Friendly ~ 1 pm Ckout ~ Hiking ~ Firepit ~ VIEWS!
- Fantasy Cottage: Private Pond, Waterfall, Hot Tub
- Rolling River Farm: Exquisite Riverfront Paradise
- Spacious Cabin on Cedar Creek, Shenandoah's hidden getaway!
- Country Elegance overlooking the Shenandoah River
- Riverfront - Happy Peach on the Shenandoah
- The Nest at Chester Gap
- Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
- Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
What is the best all-inclusive resort for families in Winchester?
Most of our listed resorts are suitable for families in Winchester. Filter your all-inclusive resorts Winchester with a family-friendly option to see which ones are right for you.
Are there pools in resorts near Winchester?
Yes, there are more than 396 resorts in Winchester that have indoor and private swimming pools. Check out our filter option and find your best resort near Winchester.
What is the price for luxury resorts in Winchester?
At Vacation Cottage, the rate for luxury resorts in Winchester per night starts from $42. Our partner provides these prices & we calculated the average daily rate in Winchester. Please see our partner's price for more details.
Do you have resorts in Winchester that allow pets?
Yes. We have all-inclusive resorts in Winchester that allow pets. Some of the top pet-friendly resorts in Winchester are:
- The Nest at Chester Gap
- Multi-gen Family Mountain House
- Cleveland Park awesome Winchester 2 BR 1st fl napt. walk to everything!
- Beautifully Restored Log Cabin in Bluemont, VA
You can see all pet-friendly places to stayin Winchester on Vacation Cottage
What are the best resorts in Winchester?
Most of the resorts are perfect for travelers, but based on guest reviews in 2025, the best resorts in or near Winchester are:
- The Nest at Chester Gap
- Multi-gen Family Mountain House
- Cleveland Park awesome Winchester 2 BR 1st fl napt. walk to everything!
- Beautifully Restored Log Cabin in Bluemont, VA
Which resorts in Winchester are romantic?
Some of the resorts in Winchester have been described as romantic by other travelers:
