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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 83 Cottages in Upperville with updated reviews, rates, and availability.

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Bar (on property)

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (26)
"Our hosts were so wonderful!! The cottage is so cute and has everything one could need. We will definitely be repeat guests and recommend this place HIGHLY!!!"
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

10.0 out of 10, Exceptional, (1)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (40)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,443 total
includes taxes & fees
8 May - 9 May
18th Century Stone Cottage minutes from historic Middleburg
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (40)
"Had a wonderful stay - - beautiful country and delightful cottage."
Historical cottage in the town of Paris
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Terrace/patio

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

9.4 out of 10, Exceptional, (8)
"What a stay. Beautiful property, excellent communication with the host, very nice accommodations. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is AED 470
AED 1,762 total
includes taxes & fees
14 May - 15 May
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Dining

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.6 out of 10, Exceptional, (10)
"Excellent place to stay. Shelly is an excellent host. Nice location "
The price is AED 1,313
AED 1,842 total
includes taxes & fees
7 May - 8 May
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

10.0 out of 10, Exceptional, (16)
"We loved this place! It had everything we needed and everything was very comfortable. The sunset view from the hot tub was a highlight! We would stay here again."
The price is AED 367
AED 1,386 total
includes taxes & fees
1 May - 2 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (27)
"Great location"
The price is AED 775
AED 1,690 total
includes taxes & fees
5 May - 6 May
Royal Heritage Home @ Historic Leesburg
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is AED 371
AED 1,310 total
includes taxes & fees
5 May - 6 May
Lake View Retreat - Cottage Near a Peaceful Lake!
Cottage at Gray Fox- Many Attraction- Pet Friendly
Aerial view

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Very peaceful stay in the mountains. Would book again!"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (20)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
The price is AED 400
AED 1,304 total
includes taxes & fees
13 May - 14 May
Woodsy Retreat with a Hot Tub and Seasonal Views!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is AED 918
AED 1,533 total
includes taxes & fees
1 May - 2 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Chic Front Royal Retreat Near Shenandoah River!
Terrace/patio

Chic Front Royal Retreat Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Cozy Bear Chase Cottage
Fridge, microwave, oven, stovetop

Cozy Bear Chase Cottage

10.0 out of 10, Exceptional, (35)
"The staff and property were wonderful. Everyone was so helpful; it was nice to be able to walk up to the restaurant and see the amazing mountain views with fire pits and lookouts. It was an added surprise to see the home decorated for the holidays! "
Cozy Bear Chase Cottage
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (25)
"Really enjoyed stay home was great "
The price is AED 404
AED 1,391 total
includes taxes & fees
6 May - 7 May
Peaceful Lakefront Cottage with Mountain Views!
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Pool

Cozy Virginia Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (16)
"Our stay was fabulous! The cottage is clean, comfortable, and in a peaceful location. The host checked in on us and left a nice welcome gift. I would definitely recommend staying here if in the area."
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Wild Hare Cottage
2 bedrooms, WiFi

Wild Hare Cottage

10.0 out of 10, Exceptional, (4)
"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"
The price is AED 514
AED 858 total
includes taxes & fees
14 May - 15 May
Wild Hare Cottage
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Terrace/patio

CEDAR LANE - Private Cottage, Sophisticated Country Charm

10.0 out of 10, Exceptional, (148)
"Wonderful stay!"
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Property grounds

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

10.0 out of 10, Exceptional, (1)
"This treehouse was so dreamy and private! I hope we get to stay here again some time soon!"
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"The cabin is beautiful and tucked away in the trees. Amazing colors this time of year and was such a great little getaway. Highly recommend staying here!"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (40)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,443 total
includes taxes & fees
8 May - 9 May
18th Century Stone Cottage minutes from historic Middleburg
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (64)
"The cabin was very nice and quaint. We had a nice stay. The view from the sunroom is great amazing. The place is very cozy and made for a great night away. "
The price is AED 588
AED 1,288 total
includes taxes & fees
27 May - 28 May
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.