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Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured Cottages in Upperville

Our top choices for Upperville cottages

Hunt Country cottage in Upperville!
Exterior

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (21)
"Beautiful cottage!! Incredibly comfortable! Loved it!!"
Hunt Country cottage in Upperville!
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (48)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Terrace/patio

CEDAR LANE - Private Cottage, Sophisticated Country Charm

10.0 out of 10, Exceptional, (150)
"We have stayed here before and love it so much! Perfectly appointed, idyllic setting!"
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Cottage w/ Hot Tub and 100-Mile Valley Views!
Property grounds

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

10.0 out of 10, Exceptional, (19)
"Pretty cabin with a wonderful view, especially from the hot tub. We will return!"
The price is NZ$644
includes taxes & fees
23 Sept - 24 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

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

9.8 out of 10, Exceptional, (6)
"It was a great place to starve whole experience was perfect. "
The price is NZ$675
includes taxes & fees
28 Sept - 29 Sept
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
The Vue - Mountain top hot tub overlooking the Shenandoah River
Property grounds

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
9.8 out of 10, Exceptional, (6)
"Love the view and beautiful appointed decor throughout the home…"
The price is NZ$608
includes taxes & fees
30 Sept - 1 Oct
The Vue - Mountain top hot tub overlooking the Shenandoah River
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Property grounds

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

9.8 out of 10, Exceptional, (7)
"Our rental space was on the top floor and the area was nice for our getaway. Host was quick to reply when we had a question. I would stay here again."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (14)
"We had a great time over Thanksgiving. The house , yard and host were all great. I woood definitely stay here again. "
Cozy Mountain Cottage - Perfect for Friends, Family
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, (21)
"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."
The price is NZ$570
includes taxes & fees
29 Sept - 30 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
Weekend getaway short distance from DC/Northern Virginia
Property grounds

Weekend getaway short distance from DC/Northern Virginia

10.0 out of 10, Exceptional, (87)
"This place was cozy and welcoming, exactly what we were looking for on a weekend away."
Weekend getaway short distance from DC/Northern Virginia
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (47)
"What a peaceful place and wonderful views."
18th Century Stone Cottage minutes from historic Middleburg
Wild Hare Cottage
Terrace/patio

Wild Hare Cottage

10.0 out of 10, Exceptional, (7)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
The price is NZ$407
includes taxes & fees
24 Sept - 25 Sept
Wild Hare 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, (18)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is NZ$614
includes taxes & fees
25 Sept - 26 Sept
Lake View Retreat - Cottage Near a Peaceful Lake!
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.

9.6 out of 10, Exceptional, (14)
"The cottage was large, quaint, well appointed, and clean. The farm setting was peaceful andtbeautiful. The host were extremely attentive and a pleasure to deal with. We loved our stay!extremely "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Cozy Stone Cottage in Round Hill, VA
Exterior

Cozy Stone Cottage in Round Hill, VA

9.6 out of 10, Exceptional, (9)
"Really enjoyed our stay! Would recommend for sure "
Cozy Stone Cottage in Round Hill, VA
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.8 out of 10, Exceptional, (13)
"What a beautiful little house!! And can’t beat the magnificent view of the river! "
The price is NZ$641
includes taxes & fees
23 Sept - 24 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Modern Country Cottage in Wine Country
Exterior

Modern Country Cottage in Wine Country

8.6 out of 10, Excellent, (4)
"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"
Modern Country Cottage in Wine Country
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, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Peaceful Lakefront Cottage with Mountain Views!
Property grounds

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (29)
"Really enjoyed stay home was great "
The price is NZ$646
includes taxes & fees
1 Oct - 2 Oct
Peaceful Lakefront Cottage with Mountain Views!
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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Top Upperville Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Close to route 81"
tomasz 1-night trip
Posted 3 days ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Upperville

Find out more about Upperville

Upperville Cottages information

Number of reviews
539
Accommodation
89 Cottages
Lowest Price
NZ$407
Highest Price
NZ$675

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