A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

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Check prices for these dates

Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Upperville bed & breakfast

Outdoor dining

1. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (71 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveler
The price is AED 1,194
AED 1,549 total
includes taxes & fees
20 Sep - 21 Sep
The Van Gogh Room in Villa
Hallway

2. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (140 reviews)
"A very beautiful experience. The staff was amazing. The country club access was such a treat. The room was breathtaking. We can’t wait to go back:"
United States
Adriane
The price is AED 884
AED 1,008 total
includes taxes & fees
20 Oct - 21 Oct
Inn at Evergreen
Reception

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (332 reviews)
"Great location and service. A perfect weekend getaway from DC or Richmond."
United States
Mindi
The price is AED 551
AED 628 total
includes taxes & fees
20 Sep - 21 Sep
Loudoun Valley Manor
Front of property

4. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
The price is AED 542
AED 699 total
includes taxes & fees
21 Sep - 22 Sep
Hillbrook Inn
Outdoor dining

5. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is AED 1,469
AED 2,022 total
includes taxes & fees
21 Sep - 22 Sep
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Exterior

6. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (98 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is AED 1,245
AED 1,436 total
includes taxes & fees
21 Sep - 22 Sep
Glen Gordon Manor
Exterior

7. Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
The price is AED 1,157
AED 1,499 total
includes taxes & fees
27 Sep - 28 Sep
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

8. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"We only spent one night here because my wife had training in the town of Purcellville. However, we were treated like family. Kenny, the general manager, was very kind, welcoming and attentive. He personally prepared our breakfast. Noé, the caretaker was wonderful and always available to us. Beyond that, this is one of the most beautiful, scenic properties I have ever experienced. You have to see it for yourself. Highly recommended!"
United States
Andrew
The price is AED 1,028
AED 1,323 total
includes taxes & fees
26 Sep - 27 Sep
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Interior entrance

9. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
The price is AED 2,142
AED 2,441 total
includes taxes & fees
20 Sep - 21 Sep
The Inn at Grass Roots Hill
Exterior

10. Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included

Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
The price is AED 1,286
AED 1,600 total
includes taxes & fees
25 Sep - 26 Sep
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Exterior

11. Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included

Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
Purcellville
The price is AED 1,414
AED 1,759 total
includes taxes & fees
25 Sep - 26 Sep
Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
Exterior

12. Lakefront B&B Room w/Private Island Access + Breakfast Included

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
The price is AED 1,513
AED 1,960 total
includes taxes & fees
23 Sep - 24 Sep
Lakefront B&B Room w/Private Island Access + Breakfast Included
Exterior

13. Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
The price is AED 42,240
AED 56,081 total
includes taxes & fees
20 Sep - 21 Sep
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Front of property

14. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (456 reviews)
"Amazing place with incredible history!"
United States
Andrea
The price is AED 582
AED 657 total
includes taxes & fees
28 Sep - 29 Sep
The Carriage Inn B&B
Exterior

15. 5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included

5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Purcellville
The price is AED 6,960
AED 10,028 total
includes taxes & fees
25 Sep - 26 Sep
5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"J"
Charles 2-night trip
Posted 6 hours ago
Quality Inn Winchester

Frequently asked questions

Searching for B&Bs in Upperville?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a bed and breakfast might be a great fit for your vacation to Upperville. If your ideal vacation to Upperville includes spending lots of time outside, Upperville Park is a good spot to enjoy the scenery.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to interact with the owner, and breakfast served on site, B&Bs all have a unique environment.
What are the best bed and breakfasts in Upperville?
Here are some well-liked B&Bs in the surrounding area: Hillbrook Inn: 9 rooms. 18.2 mi (29.3 km) from the heart of Upperville. Enjoy the free full breakfast and fitness center. Loudoun Valley Manor: 6 rooms. Situated 18 mi (29 km) from the heart of Upperville. Enjoy the local cuisine breakfast and soaking bathtubs. Inn at Evergreen: 11 rooms. 14.2 mi (22.8 km) from the heart of downtown. Enjoy the free full breakfast and on-site golf. The Van Gogh Room in Villa: Located 8.7 mi (14.1 km) from the core of Upperville. Enjoy the in-room pools and limo or town car service.
When should I book my B&B in Upperville?
When you're dreaming of a escape to Upperville, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Upperville is 44 inches.
What is there to do in Upperville?
When you want to check out some attractions in town, you might consider a visit to Sky Meadows State Park and Upperville Park. Delaplane Cellars and RdV Vineyards are also some sites to visit if you want to see more of the area.
How can I get to and around Upperville?
Mapping out your trip in and around Upperville is easy with these transportation options. Fly into Washington Dulles Intl. Airport (IAD), which is located 23.7 mi (38.2 km) from the city center. Otherwise, you can search for flights to Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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