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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

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

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

9.8 out of 10, Exceptional, (26)
"Good location. Large fenced in yard. Plenty of room. Would book again."
The price is AED 1,078
AED 2,368 total
includes taxes & fees
16 Apr - 17 Apr
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, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AED 1,010
AED 1,466 total
includes taxes & fees
17 Apr - 18 Apr
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, (39)
"We loved our stay at the cottage! Will is a wonderful host!"
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)
"Overall we loved the place. The beds slept great even the sofa bed. They had a nice thick memory foam for it. The grounds were beautiful and we had a garage to pull into to get out of the weather. The only complaint one of the girls had was the shower was not for big girls. It was a tight squeeze but we totally enjoyed it and will rebook in warmer weather. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

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 639
AED 1,975 total
includes taxes & fees
28 Apr - 29 Apr
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Outdoor spa tub

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 1,862 total
includes taxes & fees
6 May - 7 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, (15)
"The view of this house is amazing! Absolutely beautiful!"
The price is AED 489
AED 1,564 total
includes taxes & fees
23 Apr - 24 Apr
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (25)
"The house was simply perfect for our stay. All you can ask for. Our daughter’s wedding was near by and wanted to explore downtown Leesburg as well. Everything was walkable and so many places to explore. Michael the host was amazing and hospitality 5 stars!!! We will definitely book again when in the area. "
The price is AED 775
AED 1,719 total
includes taxes & fees
14 Apr - 15 Apr
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)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is AED 408
AED 1,375 total
includes taxes & fees
24 Apr - 25 Apr
Lake View Retreat - Cottage Near a Peaceful Lake!
Cottage at Gray Fox- Many Attraction- Pet Friendly
Fridge, microwave, oven, stovetop

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Wonderful property for a girls' getaway! The owners are very responsive to messages and communicated well with us. Clean, comfy beds, had everything we needed. The hot tub was a plus on a snowy weekend."
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)
"This property was everything we hoped for in a weekend getaway home! So clean, beautifully decorated, and decked out with everything we wanted and more. We will definitely be booking with Mountain Mama again. "
The price is AED 463
AED 1,377 total
includes taxes & fees
24 Apr - 25 Apr
Woodsy Retreat with a Hot Tub and Seasonal Views!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

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 1,558 total
includes taxes & fees
14 Apr - 15 Apr
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
TV, fireplace

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, (24)
"Wintertime visit. Very peaceful. "
The price is AED 757
AED 1,879 total
includes taxes & fees
21 Apr - 22 Apr
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)
"I have never felt more welcomed at a VRBO. Our host, Linny, goes out of her way to make you feel at home. From the excellent communication starting from the reservation and continuing throughout the stay to farm fresh eggs, orange juice, muffins, and wine awaiting our arrival. I highly recommend this VRBO and will definitely making another reservation here soon."
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Wild Hare Cottage
2 bedrooms, WiFi

Wild Hare Cottage

10.0 out of 10, Exceptional, (4)
"We stayed a few nights at Wild Hare and could not have loved it more. It’s so nicely decorated and clean. You can tell they put a lot of thought into their guests, no detail was missed. We definitely would love to come back!"
The price is AED 514
AED 875 total
includes taxes & fees
16 Apr - 17 Apr
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!
Smart TV

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.
Exterior

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (84)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
2 bedrooms, in-room safe, desk, iron/ironing board

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

10.0 out of 10, Exceptional, (60)
"The cabin was beautiful! Brigid has the cabin well stocked. She was very welcoming. Our family with kids and a dog felt very comfortable and even pampered!"
The price is AED 588
AED 1,280 total
includes taxes & fees
6 May - 7 May
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AED 1,010
AED 1,466 total
includes taxes & fees
17 Apr - 18 Apr
18th Century Stone Cottage minutes from historic Middleburg
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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