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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Middletown bed & breakfast

A covered porch with a bench, two red chairs, and a table. There are three pumpkins on the ground.

1. Dandelion in the Heart of Boonsboro

Dandelion in the Heart of Boonsboro
Boonsboro
10.0 out of 10, Exceptional, (3 reviews)
"Loved this property! Quaint and clean. House cats were my favorite feature. They were living and sweet. Thoroughly enjoyed our stay. Thank you Heidi!"
United States
Rebecca G.
$117 nightly
The price is $131
Nov 17 - Nov 18
Total with taxes and fees
Dandelion in the Heart of Boonsboro
A two-story house with a dark roof, a visible chimney, and a well-lit entrance.

2. Antietam Overlook Farm

Antietam Overlook Farm
3.5 star property
Keedysville
9.8 out of 10, Exceptional, (248 reviews)
"Really welcoming and relaxing atmosphere."
United States
Michael
$233 nightly
The price is $258
Nov 15 - Nov 16
Total with taxes and fees
Antietam Overlook Farm
A two-story house with a porch and a staircase leading to the front door.

3. Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast
3.5 star property
Frederick
9.6 out of 10, Exceptional, (106 reviews)
"Enjoyed the stay on our road trip. Would recommend"
United States
Will
$229 nightly
The price is $243
Nov 10 - Nov 11
Total with taxes and fees
Hollerstown Hill Bed and Breakfast
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (162 reviews)
"Great place and breakfast was amazing!!"
United States
Rich
$158 nightly
The price is $170
Nov 22 - Nov 23
Total with taxes and fees
Light Horse Inn
A gazebo with a brick pathway leading to it, surrounded by a grassy area with purple flowers.

5. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (340 reviews)
"Very nice with adjacent winery!"
United States
Julia
$138 nightly
The price is $157
Dec 10 - Dec 11
Total with taxes and fees
Loudoun Valley Manor
A two-story house with a front porch, American flags, and a mailbox.

6. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.8 out of 10, Exceptional, (467 reviews)
"Beautiful place. Cookies were nice in the evenings and breakfast was delicious."
United States
Meredith
$163 nightly
The price is $184
Nov 10 - Nov 11
Total with taxes and fees
The Carriage Inn B&B
An outdoor patio area with tables and chairs, umbrellas, barrels, and a wooden building.

7. Stable & Vine

Stable & Vine
3.5 star property
Leesburg
10.0 out of 10, Exceptional, (7 reviews)
"Really nice property, very clean very quiet. off the beaten path, perfect for us"
United States
david
$250 nightly
The price is $285
Dec 10 - Dec 11
Total with taxes and fees
Stable & Vine
A brick building with blue shutters and a porch.

8. The Amberson House Bed & Breakfast

The Amberson House Bed & Breakfast
3.0 star property
Waynesboro
10.0 out of 10, Exceptional, (236 reviews)
"Perfect experience in Waynesboro! Staff exceptional and helpful!"
United States
Alicia
$220 nightly
The price is $244
Nov 11 - Nov 12
Total with taxes and fees
The Amberson House Bed & Breakfast
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

9. 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.
$12,135 nightly
The price is $14,409
Nov 11 - Nov 12
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

10. 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
Nov 10 - Nov 11
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.

11. 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, (3 reviews)
"My husband and I were only there one night but it was beautiful and so welcoming. We would absolutely stay again."
United States
Lindsey S.
$293 nightly
The price is $334
Nov 16 - Nov 17
Total with taxes and fees
Cozy Lakefront 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 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
$330 nightly
The price is $376
Nov 16 - Nov 17
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.

13. 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
$367 nightly
The price is $418
Nov 16 - Nov 17
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.

14. 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
$403 nightly
The price is $459
Nov 16 - Nov 17
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.

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

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
$418 nightly
The price is $477
Nov 15 - Nov 16
Total with taxes and fees
Lakefront B&B Room w/Private Island Access + Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

16. 5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included

5BR Lakefront Estate w/Private Island Access / Entire House + Breakfast Included
Purcellville
$2,317 nightly
The price is $2,641
Nov 16 - Nov 17
Total with taxes and fees
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.
View all properties

Learn more about Middletown

Nestled in the scenic Middletown Valley, this historic town offers charming Main Street shops and the annual Middletown Heritage Festival each September. Outdoor enthusiasts can explore nearby South Mountain State Park's hiking trails or visit local wineries for tastings with spectacular valley views.

See all hotels in Middletown
A stone tower with a staircase leading up to it.

Top reviews in Middletown

A two-story house with a dark roof, a visible chimney, and a well-lit entrance.
Antietam Overlook Farm

Antietam Overlook Farm

Antietam Overlook Farm
Keedysville

10/10 Excellent

Wonderful friendly people, charming rooms, spectacular views both in the day, at sunset (straight on view over the valley) and at night (black sky, tons of stars). HUGE tasty breakfast, complementary chardonnay, just so pleasant and relaxing in every way.
United States
Anonymous traveler
Reviewed June 25, 2021
Antietam Overlook Farm

Frequently Asked Questions

What is the nightly rate for a Bed and Breakfast in Middletown?

Prices for B&Bs in Middletown often vary, but you can find a great deal from $130 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middletown 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.

What is the difference between a Middletown B&B and a hotel?

Every Middletown 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 Middletown B&Bs.

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