Top 50 Upperville Vacation Rentals

Houses (38)
Cottages (16)
Cabins (14)
Golf rental (57)
Mountain view (52)
Beachfront (10)

Explore a selection of Upperville vacation rentals

The Outpost Cottage In Upperville/Middleburg
Guests2
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$236 avg/night
1 bed
1 Bathroom
Guests 2
9 reviews
Hunt Country Cottage
Guests7
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$275 avg/night
3 beds
2 Bathrooms
Guests 7
22 reviews
Cute 2BR/2BA Cottage in Virginia's Hunt Country.
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$145 avg/night
2 beds
2 Bathrooms
Guests 4
9 reviews
Large Modern House in Virginia Wine Country
Guests12
Bedrooms6
Bathrooms3
Wonderful 0 / 5
$226 avg/night
6 beds
3 Bathrooms
Guests 12
Historic Manor House on Shenandoah River in Virginia's Wine Country
Guests14
Bedrooms5
Bathrooms2
Wonderful 5 / 5
$536 avg/night
5 beds
2 Bathrooms
Guests 14
54 reviews
Fantasy Getaway Cottage on Private Pond with Waterfall, Rock Pool...
Guests4
Studio
Bathroom1
Wonderful 4.9 / 5
$257 avg/night
Studio
1 Bathroom
Guests 4
60 reviews
Spectacular Cottage Overlooking the Shenandoah River and Blue...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$349 avg/night
3 beds
2 Bathrooms
Guests 10
93 reviews
Exquisite Riverfront Paradise...100+ Acres- Hike, Boat, Swim...
Guests9
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$324 avg/night
3 beds
2 Bathrooms
Guests 9
61 reviews
Sleeps 6, in the middle of Loudoun County wine country
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$149 avg/night
3 beds
2 Bathrooms
Guests 6
55 reviews
Farmhouse located in Shenandoah Wine Country near Winchester
Guests14
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$250 avg/night
5 beds
3 Bathrooms
Guests 14
141 reviews
Farmhouse located in Shenandoah Wine Country
Guests14
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$220 avg/night
5 beds
3 Bathrooms
Guests 14
141 reviews
Estate Victorian/Sleeps 18(56 w/Farmhouse & Cottage)Hot...
Guests18
Bedrooms6
Bathrooms4
Wonderful 4.9 / 5
$664 avg/night
6 beds
4 Bathrooms
Guests 18
30 reviews
The Country House, Horse Country, Near Wineries, Fall Special...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$300 avg/night
3 beds
2 Bathrooms
Guests 6
13 reviews
A mountain retreat, solitude for singles, a romantic getaway for...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$130 avg/night
1 bed
1 Bathroom
Guests 4
43 reviews
Luxurious Chalet, Incredible Views, Stunning Sunsets, Plus...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$320 avg/night
4 beds
3 Bathrooms
Guests 10
31 reviews
Paradise in the Virginia Wine trail and horse country
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.7 / 5
$314 avg/night
4 beds
2 Bathrooms
Guests 10
38 reviews
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in...
Guests3
Bedroom1
Bathroom1
Wonderful 5 / 5
$133 avg/night
1 bed
1 Bathroom
Guests 3
8 reviews
Rainbow View Cabin - Blue Ridge Mtn Retreat with Shenandoah Valley...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$169 avg/night
2 beds
1 Bathroom
Guests 4
202 reviews
The Nest in Chester Gap
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$395 avg/night
2 beds
2 Bathrooms
Guests 6
17 reviews
Charming Writer's Cottage In The Heart Of Middleburg
Guests2
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$157 avg/night
1 bed
1 Bathroom
Guests 2
12 reviews
Summit Hill Mountain home- Blue Ridge Mtn Hottub Pet friendly
Guests6
Bedrooms2
Bathroom1
Wonderful 5 / 5
$88 avg/night
2 beds
1 Bathroom
Guests 6
7 reviews
Comfortable And Spacious Home In Horse Country
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 6
96 reviews
Charming, Cozy, Secluded Mountain Cabin
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 4
15 reviews
Beautiful Home Overlooking Shenandoah River
Guests7
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$353 avg/night
4 beds
3 Bathrooms
Guests 7
32 reviews
Perfect Hunt Box in Clarke Co. Minutes to Upperville and...
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$171 avg/night
2 beds
1 Bathroom
Guests 4
5 reviews
Romantic, Secluded, Rustic Mtn. Cabin in the Woods
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$171 avg/night
3 beds
2 Bathrooms
Guests 8
8 reviews
Rustic Elegance on the Legendary Shenandoah River
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$356 avg/night
3 beds
3 Bathrooms
Guests 8
12 reviews
Dome Of Your Dreams!
Guests14
Bedrooms2
Bathrooms3
Wonderful 4.1 / 5
$190 avg/night
2 beds
3 Bathrooms
Guests 14
7 reviews
Tyrolean Garden Suite With Pool and Private Entrance In Art Villa
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$125 avg/night
1 bed
1 Bathroom
Guests 2
3 reviews
Comfortable and Charming Home Furnished to Accomodate Your...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.5 / 5
$228 avg/night
4 beds
2 Bathrooms
Guests 10
19 reviews
Wonderful Stone Cottage on Large Horse Farm with Fireplace
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$171 avg/night
2 beds
1 Bathroom
Guests 5
5 reviews
Valley Vista Cabin - Blue Ridge Mtn Retreat with Shenandoah Valley...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$217 avg/night
3 beds
2 Bathrooms
Guests 6
7 reviews
Mortgage Hall Middleburg, Virginia
Guests20
Bedrooms9
Bathrooms5
Wonderful 5 / 5
$900 avg/night
9 beds
5 Bathrooms
Guests 20
4 reviews
COTTAGE Charming Best Describes this Country Cottage SLEEPS 14-30...
Guests14
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$467 avg/night
4 beds
3 Bathrooms
Guests 14
27 reviews
Turquoise room at Loudoun Valley Manor - near Leesburg, VA
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$68 avg/night
1 bed
1 Bathroom
Guests 2
7 reviews
Appalachian Estates Cabin
Guests8
Bedrooms3
Bathrooms2
Wonderful 4 / 5
$218 avg/night
3 beds
2 Bathrooms
Guests 8
1 reviews
DISCOUNTED RATE - Avail. wk. of Sept. 23 -30 due to cancellation!
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$214 avg/night
3 beds
2 Bathrooms
Guests 8
19 reviews
Incredible Home w/Hot Tub, Heated Pool, 10 Minutes from Middleburg...
Guests10
Bedrooms6
Bathrooms2
Wonderful 5 / 5
$950 avg/night
6 beds
2 Bathrooms
Guests 10
75 reviews
Hot Tub Heaven #1 Vacation Cabin. Dog Friendly!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$164 avg/night
2 beds
1 Bathroom
Guests 4
1 reviews
Franklin Manor _ Luxury Log Home On Q Acres And Close To Local...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.1 / 5
$236 avg/night
3 beds
3 Bathrooms
Guests 8
10 reviews
Hot Tub Heaven #3 Vacation Cabin. Dog Friendly!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$184 avg/night
2 beds
1 Bathroom
Guests 4
39 reviews
Sienna room at Loudoun Valley Manor - near Leesburg, VA
Guests2
Bedroom1
Bathroom1
Wonderful 4.4 / 5
$70 avg/night
1 bed
1 Bathroom
Guests 2
7 reviews
Golden room for Route 9 travelers - 7 min from Leesburg
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$88 avg/night
1 bed
1 Bathroom
Guests 2
2 reviews
Lovely stone house with unspoilt views of the Blue Ridge in VA...
Guests10
Bedrooms5
Bathrooms5
Wonderful 0 / 5
$833 avg/night
5 beds
5 Bathrooms
Guests 10
"The House Above the Barn" at MEA Haven Farm
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$129 avg/night
3 beds
2 Bathrooms
Guests 8
4 reviews
BOOK NOW THRU SEPT. 23 and GET POLO & WINE TASTING FREE
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$175 avg/night
1 bed
1 Bathroom
Guests 2
3 reviews
Green room (suite) at Loudoun Valley Manor
Guests2
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$84 avg/night
1 bed
1 Bathroom
Guests 2
3 reviews
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly...
Guests14
Bedrooms6
Bathrooms3
Wonderful 5 / 5
$975 avg/night
6 beds
3 Bathrooms
Guests 14
1 reviews
Beautiful Cottage set in rolling hills near Middleburg...
Guests3
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$142 avg/night
1 bed
1 Bathroom
Guests 3
6 reviews
Hot Tub Heaven #9 Vacation Cabin. Dog Friendly!
Guests8
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$279 avg/night
4 beds
2 Bathrooms
Guests 8
6 reviews

Upperville, VA, USA Vacation Rentals

The Outpost Cottage In Upperville/Middleburg

Hunt Country Cottage

Cute 2BR/2BA Cottage in Virginia's Hunt Country.

Large Modern House in Virginia Wine Country

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

Fantasy Getaway Cottage on Private Pond with Waterfall, Rock Pool...

Spectacular Cottage Overlooking the Shenandoah River and Blue...

Exquisite Riverfront Paradise...100+ Acres- Hike, Boat, Swim...

Sleeps 6, in the middle of Loudoun County wine country

Farmhouse located in Shenandoah Wine Country near Winchester

Farmhouse located in Shenandoah Wine Country

Estate Victorian/Sleeps 18(56 w/Farmhouse & Cottage)Hot...

The Country House, Horse Country, Near Wineries, Fall Special...

A mountain retreat, solitude for singles, a romantic getaway for...

Luxurious Chalet, Incredible Views, Stunning Sunsets, Plus...

Paradise in the Virginia Wine trail and horse country

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in...

Rainbow View Cabin - Blue Ridge Mtn Retreat with Shenandoah Valley...

The Nest in Chester Gap

Charming Writer's Cottage In The Heart Of Middleburg

Summit Hill Mountain home- Blue Ridge Mtn Hottub Pet friendly

Comfortable And Spacious Home In Horse Country

Charming, Cozy, Secluded Mountain Cabin

Beautiful Home Overlooking Shenandoah River

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

Romantic, Secluded, Rustic Mtn. Cabin in the Woods

Rustic Elegance on the Legendary Shenandoah River

Dome Of Your Dreams!

Tyrolean Garden Suite With Pool and Private Entrance In Art Villa

Comfortable and Charming Home Furnished to Accomodate Your...

Wonderful Stone Cottage on Large Horse Farm with Fireplace

Valley Vista Cabin - Blue Ridge Mtn Retreat with Shenandoah Valley...

Mortgage Hall Middleburg, Virginia

COTTAGE Charming Best Describes this Country Cottage SLEEPS 14-30...

Turquoise room at Loudoun Valley Manor - near Leesburg, VA

Appalachian Estates Cabin

DISCOUNTED RATE - Avail. wk. of Sept. 23 -30 due to cancellation!

Incredible Home w/Hot Tub, Heated Pool, 10 Minutes from Middleburg...

Hot Tub Heaven #1 Vacation Cabin. Dog Friendly!

Franklin Manor _ Luxury Log Home On Q Acres And Close To Local...

Hot Tub Heaven #3 Vacation Cabin. Dog Friendly!

Sienna room at Loudoun Valley Manor - near Leesburg, VA

Golden room for Route 9 travelers - 7 min from Leesburg

Lovely stone house with unspoilt views of the Blue Ridge in VA...

"The House Above the Barn" at MEA Haven Farm

BOOK NOW THRU SEPT. 23 and GET POLO & WINE TASTING FREE

Green room (suite) at Loudoun Valley Manor

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

Beautiful Cottage set in rolling hills near Middleburg...

Hot Tub Heaven #9 Vacation Cabin. Dog Friendly!