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

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    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Upperville bed & breakfast

Two people seated at a table with a view of a sunset over a hilly landscape.

1. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (72 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
$370 nightly
The price is $422
Oct 2 - Oct 3
Total with taxes and fees
The Van Gogh Room in Villa
Two people seated at a table with a view of a sunset over a hilly landscape.

2. 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.
$483 nightly
The price is $551
Oct 4 - Oct 5
Total with taxes and fees
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

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
$150 nightly
The price is $171
Oct 4 - Oct 5
Total with taxes and fees
Loudoun Valley Manor
A hallway with a dark wooden floor, white walls, and a large mirror on the right. There is a door at the end of the hallway and a small table with a vase of flowers on the left.

4. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (143 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
$250 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
Inn at Evergreen
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

5. 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
$174 nightly
The price is $192
Oct 6 - Oct 7
Total with taxes and fees
Hillbrook Inn
A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

6. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (99 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
$429 nightly
The price is $495
Oct 19 - Oct 20
Total with taxes and fees
Glen Gordon Manor
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

7. 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
$316 nightly
The price is $360
Oct 8 - Oct 9
Total with taxes and fees
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

8. 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
$648 nightly
The price is $739
Oct 2 - Oct 3
Total with taxes and fees
The Inn at Grass Roots Hill
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

9. 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
10.0 out of 10, Exceptional, (1 review)
"The location was perfect since there aren’t many B&B places or hotels in Purceville. It’s a beautiful area and a beautiful venue."
United States
Kathleen
$355 nightly
The price is $405
Oct 8 - Oct 9
Total with taxes and fees
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

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
$395 nightly
The price is $450
Oct 8 - Oct 9
Total with taxes and fees
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

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
$438 nightly
The price is $499
Oct 7 - Oct 8
Total with taxes and fees
Lakefront Retreat 1 BR 1 Full Bath w/Private Island Access + Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

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

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
$462 nightly
The price is $527
Oct 19 - Oct 20
Total with taxes and fees
Lakefront B&B Room w/Private Island Access + Breakfast Included
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

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.
$13,008 nightly
The price is $15,404
Oct 5 - Oct 6
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

14. 5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included

5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Purcellville
$2,507 nightly
The price is $2,858
Oct 8 - Oct 9
Total with taxes and fees
5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
A two-story house with a front porch, American flags, and a mailbox.

15. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (458 reviews)
"Beautiful place. Cookies were nice in the evenings and breakfast was delicious."
United States
Meredith
$155 nightly
The price is $176
Oct 5 - Oct 6
Total with taxes and fees
The Carriage Inn B&B
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"I always look forward to my stay here while traveling. Always a clean room and a friendly desk staff to greet you . Nice breakfast in the morning"
Joy 1-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Winchester, VA

Find out more about Upperville

Upperville B&B information

Number of reviews
687
Accommodation
24 B&B
Lowest Price
$171
Highest Price
$15,404

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Upperville?
Prices for B&Bs in Upperville often vary, but you can find a great deal from $171 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Upperville B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Upperville?
The best time to book a B&B in Upperville is during the vibrant months of April to June, which mark the peak season for travelers seeking to immerse themselves in the region's natural beauty and outdoor activities. This time of year is especially appealing for those who appreciate the charm of Virginia's countryside, as the landscapes burst into life with lush greenery and blooming flowers, making it a superb backdrop for leisurely strolls and outdoor events.

May stands out as the most popular month, offering visitors a delightful atmosphere filled with local festivals, equestrian events, and opportunities to explore the nearby wineries. The mild temperatures, typically ranging from the mid-50s to low 80s Fahrenheit, create ideal conditions for hiking and sightseeing, allowing you to engage fully with the area's scenic trails and historic sites.

For those who are looking to travel on a budget, consider planning a visit in December. While this marks the low season, it also presents a unique opportunity to experience Upperville's winter charm, including cozy holiday decorations and local celebrations. The quieter ambiance during this time allows for a more relaxed exploration of the region's attractions.
What is the difference between a Upperville B&B and a hotel?
Every Upperville B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Upperville B&Bs.

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