Best B&B in Winchester
The Grand Castalian Inn Bed And Breakfast
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Hot spring bath
- Patio
The comfortable The Grand Castalian Inn Bed And Breakfast Berkeley Springs includes air-conditioned rooms and is located a mere 11 minutes' walk from Jules Gift Shop. Staying active is easy with a tennis court available for guests at this 3-star bed & breakfast.
Lot 12 Public House serves a good range of American food and lies in proximity to this Berkeley Springs hotel.
The Grand Castalian Inn Bed And Breakfast
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Hot spring bath
- Patio
The Grand Castalian Inn Bed And Breakfast
The comfortable The Grand Castalian Inn Bed And Breakfast Berkeley Springs includes air-conditioned rooms and is located a mere 11 minutes' walk from Jules Gift Shop. Staying active is easy with a tennis court available for guests at this 3-star bed & breakfast.
Lot 12 Public House serves a good range of American food and lies in proximity to this Berkeley Springs hotel.
Piney Hill Cottages
- In-room breakfast
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Sun terrace
Offering a sundeck and a golf course, and views of the garden, the comfortable Piney Hill Cottages Luray hotel is located 4.9 km from Cooter's Luray. This 4-star bed & breakfast offers a private parking lot on site.
Piney Hill Cottages
- In-room breakfast
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Sun terrace
Piney Hill Cottages
Offering a sundeck and a golf course, and views of the garden, the comfortable Piney Hill Cottages Luray hotel is located 4.9 km from Cooter's Luray. This 4-star bed & breakfast offers a private parking lot on site.
Bed and Breakfast Downtown Winchester
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Best-rated
Loudoun Valley Manor B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Located 4.9 km from Hillsboro Historic District, the comfortable 4-star Loudoun Valley Manor B&B Waterford offers air-conditioned rooms about a 10-minute ride from Hillsboro United Methodist Church. Guests can discover a serene oasis in this Waterford bed & breakfast's garden, where an outdoor fireplace await.
Guests can relax at the on-site outdoor bar.
Loudoun Valley Manor B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Loudoun Valley Manor B&B
Located 4.9 km from Hillsboro Historic District, the comfortable 4-star Loudoun Valley Manor B&B Waterford offers air-conditioned rooms about a 10-minute ride from Hillsboro United Methodist Church. Guests can discover a serene oasis in this Waterford bed & breakfast's garden, where an outdoor fireplace await.
Guests can relax at the on-site outdoor bar.
Gay Street Inn
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Golf centre
- Garden area
Offering various recreational opportunities, a library, and a golf course, the elegant Gay Street Inn Washington is situated in Washington, about 25 minutes' walk from Rappahannock County Library. This 4-star bed & breakfast also provides guests with Wi-Fi, available in public areas.
Inn at Little Washington is adjacent to Gay Street Inn, 550 metres away.
Gay Street Inn
- In-room breakfast
- Free parking
- Housekeeping
- Air conditioning
- Golf centre
- Garden area
Gay Street Inn
Offering various recreational opportunities, a library, and a golf course, the elegant Gay Street Inn Washington is situated in Washington, about 25 minutes' walk from Rappahannock County Library. This 4-star bed & breakfast also provides guests with Wi-Fi, available in public areas.
Inn at Little Washington is adjacent to Gay Street Inn, 550 metres away.
Romantic Bed and Breakfast Winchester
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Guest favorite
Light Horse Inn
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
The comfortable 4-star Light Horse Inn Harpers Ferry, located only 1.4 km from the True Treats Historic Candy, features a summer terrace and a picnic area. Its prime location provides easy access to the very long Appalachian National Scenic Trail, which is just 500 metres away.
The coffee bar provides you with a place to unwind. The The Barn of Harpers Ferry is around 200 metres from the Light Horse.
Light Horse Inn
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Light Horse Inn
The comfortable 4-star Light Horse Inn Harpers Ferry, located only 1.4 km from the True Treats Historic Candy, features a summer terrace and a picnic area. Its prime location provides easy access to the very long Appalachian National Scenic Trail, which is just 500 metres away.
The coffee bar provides you with a place to unwind. The The Barn of Harpers Ferry is around 200 metres from the Light Horse.
Are you in a hurry?
Here is a quick list of Bed and Breakfast in Winchester, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| The Grand Castalian Inn Bed And Breakfast |
9.5 / 10 (12 Reviews) |
From 183$ | |
| Piney Hill Cottages |
9.6 / 10 (5 Reviews) |
From 315$ | |
| Loudoun Valley Manor B&B |
9.2 / 10 (187 Reviews) |
From 170$ | |
| Gay Street Inn |
9.4 / 10 (6 Reviews) |
From 399$ | |
| Light Horse Inn |
9.0 / 10 (248 Reviews) |
From 167$ |
Frequently Asked Questions
Which boutique bed and breakfasts are near Shenandoah National Park?
Gay Street Inn and Piney Hill Cottages offer cozy stays close to Shenandoah National Park. Both feature unique designs and local charm.
Plan your visit during weekdays for quieter hiking trails at the park and try to start your hikes early in the morning to avoid crowds.
Which romantic B&Bs in Winchester provide exceptional breakfast options?
Piney Hill Cottages and Loudoun Valley Manor B&B serve gourmet breakfasts that cater to various dietary needs. Enjoy a range of homemade dishes every morning.
Request special diet options when booking to ensure delicious breakfast selections tailored to your needs.
What historic bed and breakfasts in Winchester have charming atmospheres?
The Light Horse Inn and Gay Street Inn are historic properties that capture local history and design. They provide a charming, intimate setting for guests.
Opt for guided tours of the inns to learn more about their rich histories and architectural details.
Which B&Bs near local vineyards offer wine tasting experiences?
Loudoun Valley Manor B&B and Light Horse Inn are close to popular local vineyards like Doukenie Winery. They offer easy access to wine tastings and tours.
Plan your vineyard visits during the weekends for special events or limited-edition tastings that aren't available during the week.
What B&Bs near Berkeley Springs State Park cater to families?
The Grand Castalian Inn and Loudoun Valley Manor B&B are both family-oriented, offering spacious accommodations and access to parks. They feature facilities suitable for all ages.
Bring your family swimming gear to enjoy aquatic fun at nearby water parks or pools during summer breaks.
Which pet-friendly B&Bs are recommended in Winchester?
Piney Hill Cottages and Loudoun Valley Manor B&B welcome pets and provide facilities for your furry friends. They can accommodate special requests for pet care.
Check ahead for any additional pet fees, and consider bringing pet-specific supplies for a comfy stay.
Which bed and breakfasts allow for extended stays in Winchester?
Piney Hill Cottages and The Grand Castalian Inn offer comfortable options for guests seeking longer visits. They provide amenities that make extended stays enjoyable.
Inquire about special rates for extended stays when booking; it could significantly lower your overall cost.
What unique experiences can I enjoy while staying at a Winchester B&B?
You can enjoy local wine tastings, hiking in scenic parks, and gourmet breakfasts tailored to your preferences at various B&Bs. They often feature packages for special occasions as well.
Plan your stay around local events like the Shenandoah Valley Wine and Jazz Festival in June for an unforgettable experience.
How can I get around Winchester efficiently during my stay?
While Winchester has limited public transport, using rideshare apps is reliable. Walking between neighborhood attractions is also pleasant and feasible.
Consider renting a bicycle to explore local sites such as the historic downtown area and nearby parks - it's enjoyable and cost-effective.
What should I pack when visiting Winchester in any season?
Always pack layers, especially for cooler evenings, and comfortable walking shoes for exploring outdoor activities and historic sites. Seasonal events also require different attire.
If visiting in autumn, bring binoculars for excellent bird watching opportunities in Shenandoah National Park.