Search B&B in Middletown

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Middletown bed & breakfast

Front of property
The Amberson House Bed & Breakfast

The Amberson House Bed & Breakfast

3.0 star property
Waynesboro
10.0 out of 10, Exceptional, (217)
"The hosts were extremely kind and hospitable. The b&b was gorgeous and well kept. Would definitely stay there again."
United States
Rachael
The Amberson House Bed & Breakfast
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 462
AED 522 total
includes taxes & fees
15 Dec - 16 Dec
The Carriage Inn B&B
Reception
Loudoun Valley Manor

Loudoun Valley Manor

3.0 star property
Waterford
9.6 out of 10, Exceptional, (276)
"Great location for visiting wineries"
United States
Anne
The price is AED 523
AED 597 total
includes taxes & fees
28 Dec - 29 Dec
Loudoun Valley Manor
Exterior
Antietam Overlook Farm

Antietam Overlook Farm

3.5 star property
Keedysville
10.0 out of 10, Exceptional, (220)
"The communication was wonderful. Our room was comfortable and relaxing. The view was lovely breakfast was delicious . "
United States
Chad
The price is AED 672
AED 826 total
includes taxes & fees
14 Dec - 15 Dec
Antietam Overlook Farm
Dining
Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast

3.5 star property
Frederick
9.6 out of 10, Exceptional, (93)
"Quaint property in quiet neighborhood convenient for Frederick town center. Hosts are friendly and welcoming. Comfortable room with nice breakfast. Enjoyable relaxing stay."
United States
Eric
The price is AED 781
AED 828 total
includes taxes & fees
5 Jan - 6 January 2026
Hollerstown Hill Bed and Breakfast
Garden
Stone Manor Boutique Inn

Stone Manor Boutique Inn

3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (95)
"The experience was very good, will return in the future. The breakfast was excellent. "
United States
Marvin
The price is AED 703
AED 802 total
includes taxes & fees
14 Dec - 15 Dec
Stone Manor Boutique Inn
Property entrance
The Inn at Grass Roots Hill

The Inn at Grass Roots Hill

3.0 star property
Purcellville
9.2 out of 10, Wonderful, (7)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
The price is AED 1,685
AED 1,921 total
includes taxes & fees
6 Jan - 7 January 2026
The Inn at Grass Roots Hill
Interior
Dandelion in the Heart of Boonsboro

Dandelion in the Heart of Boonsboro

Boonsboro
The price is AED 415
AED 518 total
includes taxes & fees
16 Dec - 17 Dec
Dandelion in the Heart of Boonsboro
Garden
Cantuta Inn

Cantuta Inn

3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (74)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
United States
Aleta
The price is AED 588
AED 658 total
includes taxes & fees
14 Dec - 15 Dec
Cantuta Inn
Exterior
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

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

2.0 star property
Lovettsville
10.0 out of 10, Exceptional, (1)
"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 6,483
AED 8,666 total
includes taxes & fees
14 Dec - 15 Dec
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
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 Middletown Hotel Reviews

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

10/10 Excellent
" Needed a room for one night while visiting my daughter at college in Purcellville and to attend a church service at Cornerstone Chapel in Leesburg. This hotel was convenient as well as the most economical in Leesburg having good ratings. It turned out great! Must have recently been updated because it was very clean and comfortable. The staff member at the desk for my late night checkin and early morning checkout had a great attitude, professional at the same time friendly and welcoming! Thank you, Red Roof Inn and thank you to your staff member!"
Linda 1-night trip
Posted 1 day ago
Red Roof Inn Leesburg, VA

Frequently asked questions

Searching for B&Bs in Middletown?
If you're looking for something a little more offbeat than your standard hotel experience, a bed and breakfast might be the perfect option for your trip. If you're interested in playing some golf on your trip, Maryland National Golf Club is a good spot to tee off.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs provide a unique environment.
What are the best bed and breakfasts in Middletown?
Below are some B&Bs in the area: Loudoun Valley Manor: 6 rooms. 18.6 mi (30 km) from the heart of Middletown. Enjoy the local cuisine breakfast and soaking bathtubs. Antietam Overlook Farm: 6 rooms. Situated 8.6 mi (13.8 km) from the heart of Middletown. Enjoy the free full breakfast and soaking bathtubs.
When is the best time to book my B&B in Middletown?
When you're dreaming of a getaway to Middletown, 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 36°F. Average annual precipitation for Middletown is 49 inches.
What is there to do in Middletown?
If you're looking for some activities to entertain you on your trip, consider visiting Maryland National Golf Club and Orchid Cellar Winery. You might put South Mountain State Park and Washington Monument State Park on your list if you want to see more of the area.
How can I get to and around Middletown?
Mapping out your trip in and around Middletown is easy with these transportation options. Fly into Hagerstown, MD (HGR-Hagerstown Regional), which is located 20.6 mi (33.2 km) away from the city center. Otherwise, look for flights into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 24 mi (38.6 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.