We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Upperville Holiday Apartments

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Price per night
AU$0
AU$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
50 rentals in Upperville.
Sort by:
Tripadvisor Sort
The Mill House in Upperville - Cozy  fireplace, outside bonfire - fall is here!, holiday rental in Upperville

The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Upperville

Historic Manor House on Shenandoah River in Virginia's Wine Country

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Spacious Farm House in Horse and Wine Country, holiday rental in Upperville

Spacious Farm House in Horse and Wine Country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
A Restored Wagon Barn On A 1790's Farm, holiday rental in Upperville

A Restored Wagon Barn On A 1790's Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Middleburg, VA - Private Cottage, Sophisticated Country Charm  - Newly Remodeled, holiday rental in Upperville

Middleburg, VA - Private Cottage, Sophisticated Country Charm - Newly Remodeled

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Blue Mountain Log Cabin, holiday rental in Upperville

Blue Mountain Log Cabin

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Historic and Updated Farmhouse Built in 1808, holiday rental in Upperville

Historic and Updated Farmhouse Built in 1808

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, holiday rental in Upperville

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
The Countryside Home, holiday rental in Upperville

The Countryside Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Breathtaking views  with an  indoor private pool, come escape with us, holiday rental in Upperville

Breathtaking views with an indoor private pool, come escape with us

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Save time - get the best Upperville rentals sent straight to your email!
Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor, holiday rental in Upperville

Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Upperville

Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres, holiday rental in Upperville

Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Weekend getaway short distance from DC/Northern Virginia, holiday rental in Upperville

Weekend getaway short distance from DC/Northern Virginia

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Gorgeous English Hunt Country Cottage, holiday rental in Upperville

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Upperville

Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., holiday rental in Upperville

Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi  ***ASK FOR NEW YEAR'S QUOTE***, holiday rental in Upperville

Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi ***ASK FOR NEW YEAR'S QUOTE***

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Upperville

Virginia Wine Country Retreat 60 mi. from DC

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in Upperville

Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Alpacas & The Stars at night. Private Retreat. Fun & Peace, holiday rental in Upperville

Alpacas & The Stars at night. Private Retreat. Fun & Peace

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Meadowbrook -Entire House - Close to Vineyards and Breweries, holiday rental in Upperville

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Paradise in Horse Country, holiday rental in Upperville

Paradise in Horse Country

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Upperville

Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Upperville

Historic Mountain Cottage at Blue Ridge Overlook

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country, holiday rental in Upperville

Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Gorgeous, Cozy & Spacious - 20% OFF JAN/09 to APR/02, holiday rental in Upperville

Gorgeous, Cozy & Spacious - 20% OFF JAN/09 to APR/02

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Cozy Cabin Hidden Away on a Lake!, holiday rental in Upperville

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Ruby Summit Point - Your Home at the Track, holiday rental in Upperville

Ruby Summit Point - Your Home at the Track

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, holiday rental in Upperville

The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use

3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Dome Of Your Dreams!, holiday rental in Upperville

Dome Of Your Dreams!

2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Shannondale Lake House, holiday rental in Upperville

Shannondale Lake House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Cozy Apt in Harpers Ferry by the lake!, holiday rental in Upperville

Cozy Apt in Harpers Ferry by the lake!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
The Love Cottage in Harpers Ferry by the lake!, holiday rental in Upperville

The Love Cottage in Harpers Ferry by the lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Idle Hour at Chester Gap, holiday rental in Upperville

Idle Hour at Chester Gap

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va), holiday rental in Upperville

3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va)

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Upperville

Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
The Blueridge Cabin!, holiday rental in Upperville

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
The Travelers Rest in Harpers Ferry by the lake, holiday rental in Upperville

The Travelers Rest in Harpers Ferry by the lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out
Vista Magnifique - private mountaintop estate w/ beautiful views of wine country, holiday rental in Upperville

Vista Magnifique - private mountaintop estate w/ beautiful views of wine country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Upperville

'Anny's Farm House' in Round Hill Wine Country!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Historic Virginia Wine Country Villa w/Pool & Yard, holiday rental in Upperville

Historic Virginia Wine Country Villa w/Pool & Yard

6 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pet-Friendly Home in Heart of Wine Country!, holiday rental in Upperville

Pet-Friendly Home in Heart of Wine Country!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Outpost Suite 2- A Curated Farmhouse Suite, holiday rental in Upperville

The Outpost Suite 2- A Curated Farmhouse Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Outpost Whimsical Farmhouse Retreat +Tesla Charger, holiday rental in Upperville

The Outpost Whimsical Farmhouse Retreat +Tesla Charger

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit, holiday rental in Upperville

NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Peaceful Escape near Shenandoah National Park, holiday rental in Upperville

NEW! Peaceful Escape near Shenandoah National Park

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Family Retreat w/ Deck Near Appalachian Trail, holiday rental in Upperville

NEW! Family Retreat w/ Deck Near Appalachian Trail

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cottage w 2 Private Lakes & River Access, Fire Pit, holiday rental in Upperville

Cottage w 2 Private Lakes & River Access, Fire Pit

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!, holiday rental in Upperville

Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Upperville