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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun
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."
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, (39)
"Great little cozy cottage near Middleburg with great outdoor space and all necessary amenities. Booking, check-in and communication with owner were excellent. "
The price is HK$2,134
HK$3,072 total
includes taxes & fees
28 Apr - 29 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, (40)
"we enjoy our stay everytime"
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)
"Convenient to where I needed to be. Nice property. Dogs loved the property"
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 HK$1,055
HK$3,765 total
includes taxes & fees
8 May - 9 May
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 HK$2,774
HK$4,002 total
includes taxes & fees
9 May - 10 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 HK$776
HK$2,936 total
includes taxes & fees
30 Apr - 1 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)
"The place is great! Clean, comfortable, close to downtown. The host was very responsive and friendly. "
The price is HK$1,637
HK$3,685 total
includes taxes & fees
28 Apr - 29 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 HK$776
HK$2,781 total
includes taxes & fees
27 Apr - 28 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 HK$931
HK$2,852 total
includes taxes & fees
8 May - 9 May
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 HK$1,940
HK$3,334 total
includes taxes & fees
29 Apr - 30 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
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)
"Wintertime visit. Very peaceful. "
The price is HK$1,140
HK$3,335 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)
"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 HK$1,086
HK$1,813 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!
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, (83)
"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.
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (39)
"Great little cozy cottage near Middleburg with great outdoor space and all necessary amenities. Booking, check-in and communication with owner were excellent. "
The price is HK$2,134
HK$3,072 total
includes taxes & fees
28 Apr - 29 Apr
18th Century Stone Cottage minutes from historic Middleburg
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, (61)
"It's the perfect place to stay if you're going to HF but want some distance from people/a view of the mountains. Really nice property. We'd stay again! Thanks!"
The price is HK$1,319
HK$2,806 total
includes taxes & fees
28 Apr - 29 Apr
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.