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Budget to luxury Winchester, Virginia travel and vacations. Search all the best vacation options in Winchester including accommodations, adventure travel, unique tours and much more.


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Featured Listings

1 - 20 of 25 within 100 miles of Winchester, Virginia
Afton Mountain Bed & Breakfast Afton, Virginia Bed & Breakfasts

Afton Mountain Bed & Breakfast

Afton, Virginia Bed & Breakfasts - 86.1 miles away
Come enjoy a Blue Ridge Mountain vacation in Afton, Virginia! A quaint, relaxing Victorian farmhouse close to fantastic wineries and craft breweries....
From USD $119 per night
Nature, Comfort & Simplicity, Virginia Cottages Crozet, Virginia Vacation Rentals

Nature, Comfort & Simplicity, Virginia Cottages

Crozet, Virginia Vacation Rentals - 71.5 miles away
Bedrooms: 2  Sleeps: 6  Bathrooms: 1  
Our 8 cozy vacation cottages overlook a small lake. Small kitchens with modern appliances. Linens/towels and organic coffee & teas are complimentary. Hiking, biking, & fishing ponds w/canoes on our 12...
From USD $143 per night

200 South Street Inn Charlottesville, Virginia Bed & Breakfasts

200 South Street Inn

Charlottesville, Virginia Bed & Breakfasts - 78.2 miles away
Centrally located just one mile from University of Virginia and four miles from Thomas Jefferson's home, Monticello, the Inn offers old world charm and modern conveniences. Continental breakfast and w...
From USD $110 per night
Wine and History Escapes at a Virginia B & B Orange, Virginia Bed & Breakfasts

Wine and History Escapes at a Virginia B & B

Orange, Virginia Bed & Breakfasts - 63.1 miles away
The Holladay House offers luxury accommodations in central Virginia wine country. Situated in the Main Street historic district, walk to restaurants, antique shops and art galleries. Drive to acclaim...
From USD $139 per night
Arcady Vineyard B&B Charlottesville, Virginia Bed & Breakfasts

Arcady Vineyard B&B

Charlottesville, Virginia Bed & Breakfasts - 79.9 miles away
Arcady is the only Wine Country B&B in Charlottesville with a working vineyard and offering wine tasting tours - listed on TripAdvisor as #2 of “Things to do in Charlottesville” and in Frommers V...
From USD $250 per night
Monticello Country Ballooning Charlottesville, Virginia Ballooning

Monticello Country Ballooning

Charlottesville, Virginia Ballooning - 78.1 miles away
Offering daily sunrise and sunset flights over beautiful and historic Central Virginia. We offer the only all-inclusive flight package in the area featuring local transportation, photographs and a tr...
From USD $225 per trip
The Buckhorn Inn Churchville, Virginia Bed & Breakfasts

The Buckhorn Inn

Churchville, Virginia Bed & Breakfasts - 85.3 miles away
The historic Buckhorn Inn has been hosting travelers since 1811...
From USD $135 per night
Cabins at Chesley Creek Farm Dyke, Virginia Vacation Rentals

Cabins at Chesley Creek Farm

Dyke, Virginia Vacation Rentals - 62.5 miles away
Bedrooms: 1  Sleeps: 2  Bathrooms: 1  
4 fully equipped, romantic, secluded cabins for 2 in the Blue Ridge Mountains of Virginia....
From USD $190 per night
By the Side of the Road Getaway Lodging Harrisonburg, Virginia Vacation Rentals

By the Side of the Road Getaway Lodging

Harrisonburg, Virginia Vacation Rentals - 58.8 miles away
Bedrooms: 1  Sleeps: 2  Bathrooms: 1  
Welcome to THE Getaway Lodging destination in Harrisonburg (Rockingham County) in Virginia's central Shenandoah Valley. Whether staying one night or more, our luxurious Shenandoah Valley Vacation geta...
From USD $149 per night
Joshua Wilton House Inn & Restaurant Harrisonburg, Virginia Bed & Breakfasts

Joshua Wilton House Inn & Restaurant

Harrisonburg, Virginia Bed & Breakfasts - 58.1 miles away
An elegantly restored Victorian home, Joshua Wilton House occupies a corner of the Historic Old Town district located in Downtown Harrisonburg, Virginia and is a Fine Dining Restaurant and Inn destina...
From USD $145 per night
Stonewall Jackson Inn Bed & Breakfast Harrisonburg, Virginia Bed & Breakfasts

Stonewall Jackson Inn Bed & Breakfast

Harrisonburg, Virginia Bed & Breakfasts - 57.7 miles away
Welcome to our circa-1885 restored mansion in the heart of Virginia's Shenandoah Valley! With Wayne as your host, experience Southern hospitality, vintage decor, and cozy rooms - all within walking di...
From USD $139 per night
Lantern Lane Farm Leesburg, Virginia Horseback Riding

Lantern Lane Farm

Leesburg, Virginia Horseback Riding - 14.0 miles away
Lantern Lane Farm is an equestrian training facility specializing in Horseback Riding Lessons, Horse Training in Dressage and Natural Hosemanship for all disciplines and Event Riders and Horse Boardin...
From USD $35 per trip

Briar Patch B & B Inn Middleburg, Virginia Bed & Breakfasts

Briar Patch B & B Inn

Middleburg, Virginia Bed & Breakfasts - 35.3 miles away
With its 47 rolling acres, historic lodging, mountain views, and beautiful event building for up to 200 guests, Briar Patch B&B Inn in Middleburg is an ideal location for your wedding, party, meeting,...
From USD $95 per night
Fairlea Farm Bed and Breakfast Washington, Virginia Bed & Breakfasts

Fairlea Farm Bed and Breakfast

Washington, Virginia Bed & Breakfasts - 30.9 miles away
Our guests enjoy spectacular mountain views and pasture land, a five-minute stroll from the historic village of Little Washington... Warm hospitality and a scrumptuous country breakfast in our fieldst...
From USD $155 per night
L'Auberge Provençale Boyce, Virginia Bed & Breakfasts

L'Auberge Provençale

Boyce, Virginia Bed & Breakfasts - 11.3 miles away
Set on 8 acres in the heart of Virginia Hunt country is the culinary treasure L'Auberge Provencale. With the extensive flower, herb, and vegetable gardens and orchard, this premier country inn offers ...
Contact For Rates & Specials!
The Stonewall Jackson Hotel  Staunton, VA, Virginia Hotels & Resorts

The Stonewall Jackson Hotel

Staunton, VA, Virginia Hotels & Resorts - 81.3 miles away
The Stonewall Jackson Hotel & Conference Center in downtown Staunton is an ideal location for exploring the area’s many attractions, including the Blackfriars Playhouse at the American Shakespeare C...
From USD $132 per night
Inn at Old Virginia Staunton, Virginia Bed & Breakfasts

Inn at Old Virginia

Staunton, Virginia Bed & Breakfasts - 78.5 miles away
Upon arriving at the Inn, our guests are greeted with an atmosphere that promises relaxation and evokes the comfort of being at home. Each morning you will be greeted with the smell of a homemade brea...
Contact For Rates & Specials!
Black Horse Inn Warrenton, Virginia Bed & Breakfasts

Black Horse Inn

Warrenton, Virginia Bed & Breakfasts - 39.7 miles away
Near historic Old Town Warrenton, this hunt-country estate has 9 guestrooms, manicured gardens, stone terraces and stables. Formal ballroom accommodates 200 seated guests. Weddings, Corporate Retreat...
From USD $200 per night
The Iris Inn Bed & Breakfast Waynesboro, Virginia Bed & Breakfasts

The Iris Inn Bed & Breakfast

Waynesboro, Virginia Bed & Breakfasts - 83.5 miles away
The Iris Inn Bed and Breakfast is your destination for relaxation. Situated in a mountainous setting, we are nearby wineries, breweries, theaters, shopping areas, hiking trails, festivals, and more....
From USD $149 per night


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