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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 67 Cottages in Upperville with updated reviews, rates, and availability.

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 1,458 total
includes taxes & fees
20 Mar - 21 Mar
18th Century Stone Cottage minutes from historic Middleburg
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

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (24)
"We stayed at this property during our annual visit to Leesburg. We enjoy the downtown area (easy to walk) and catching an Uber to the local vineyards! House was perfect for our group of 5. Majority of our time at the house was spent sleeping, but we all felt comfortable and had enough space. Three bathrooms were great! "
The price is AED 775
AED 1,727 total
includes taxes & fees
17 Mar - 18 Mar
Royal Heritage Home @ Historic Leesburg
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (38)
"What a lovely and comfortable cottage! "
Historical cottage in the town of Paris
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, (25)
"This was a good little cozy cottage for a weekend away with friends. Convienient to wineries and breweries. Comfy and Cozy for a 2 day getaway!"
The price is AED 1,494
AED 2,888 total
includes taxes & fees
27 Mar - 28 Mar
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
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.

9.2 out of 10, Wonderful, (7)
"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.
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, (17)
"We love it! everything was perfect 🤗 we definitely coming back ❤️"
The price is AED 367
AED 1,247 total
includes taxes & fees
13 Mar - 14 Mar
Woodsy Retreat with a Hot Tub and Seasonal Views!
Hunt Country cottage in Upperville!
Private kitchen

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (14)
"My partner and I stayed over christmas in what was the perfect cottage. If you want to believe that you're in some tiny small town america during christmas, this is the perfect place to be. It was by far the most peaceful and relaxing christmas.I've had in a long time. The stove is wonderful and makes me want to upgrade mine at my own house and the rest of the appliances are also amazing. Ten out of ten, we'll be staying again."
Hunt Country cottage in Upperville!
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 367
AED 1,386 total
includes taxes & fees
13 Mar - 14 Mar
Cottage w/ Hot Tub and 100-Mile Valley 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 1,553 total
includes taxes & fees
16 Mar - 17 Mar
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Bear Chase Cottage
Property grounds

Bear Chase Cottage

10.0 out of 10, Exceptional, (33)
"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! "
Bear Chase Cottage
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 367
AED 1,320 total
includes taxes & fees
18 Mar - 19 Mar
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)
"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
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (23)
"Wintertime visit. Very peaceful. "
The price is AED 632
AED 1,701 total
includes taxes & fees
20 Mar - 21 Mar
Peaceful Lakefront Cottage with Mountain Views!
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 1,878 total
includes taxes & fees
13 Mar - 14 Mar
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
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!
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 536
AED 1,832 total
includes taxes & fees
26 Mar - 27 Mar
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy Stone Cottage in Round Hill, VA
Fridge, microwave, oven, stovetop

Cozy Stone Cottage in Round Hill, VA

10.0 out of 10, Exceptional, (2)
"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "
Cozy Stone Cottage in Round Hill, VA
Bear Mountain Cottage
Interior

Bear Mountain Cottage

10.0 out of 10, Exceptional, (8)
"This place is beautiful, the owners are awesome, we were allowed to come up a night early due to an incoming winter storm. The owners were so helpful, i cant say enough about them."
Bear Mountain Cottage
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

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, (58)
"Fabulous steam shower, high quality linens and very comfy bed. Fred likes a firm mattress and I like soft and we were both happy and slept well in the Master. Lovely assortment of coffees and teas. And one of my favorites an electric tea kettle. . Very quiet. Beautiful sun room for dining or working or relaxing. Plenty of pillows and blankets. Bathroom well supplied. We ate in most of the time and appliances. Definitely recommend!ekettle. "
The price is AED 551
AED 1,227 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
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, (81)
"Overall rating & experience 4.5/5 Stars. Great owners who communicated very well and timely.This precious cabin is tucked in the Shenandoah mountains & is very quiet, clean and such a lovely place located by great local wineries and eateries with beautiful scenery & mountain views, The wood-burning stove was an added bonus. We all are very happy with our experience and time here(3 nights). This cabin is also very well furnished, new, very clean, and has all the necessities.We highly recommend it...
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Exterior

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.6 out of 10, Exceptional, (50)
"My husband and I along with our 2 small dogs had a wonderful stay at this lovely mountain retreat. The cabin was clean and comfortable and had everything that we needed to cook breakfast and an easy dinner each evening. The property was beautiful with lots of tall old growth trees that were beautiful with the fall colors and even though it was in a community you felt like you were in a secluded mountain retreat because most of the homes were obsured by the trees; and it is on a dead end road...
The price is AED 804
AED 941 total
includes taxes & fees
13 Mar - 14 Mar
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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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