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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Middletown bed & breakfast

Exterior

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 54,515 total
includes taxes & fees
27 Jan - 28 Jan
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Front of property

The Amberson House Bed & Breakfast

The Amberson House Bed & Breakfast
3.0 star property
Waynesboro
10.0 out of 10, Exceptional, (218 reviews)
"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
Exterior detail

Dandelion in the Heart of Boonsboro

Dandelion in the Heart of Boonsboro
Boonsboro
10.0 out of 10, Exceptional, (1 review)
"This is a charming vintage house with modern amenities. I had the best night's sleep in a cozy comfortable bedroom with the softest blanket. The host offered every variety of product in the bathroom that a guest might need or enjoy - very thoughtful touch. "
United States
Susan H.
The price is AED 415
AED 518 total
includes taxes & fees
31 Jan - 1 Feb
Dandelion in the Heart of Boonsboro
Reception

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (279 reviews)
"Great location for visiting wineries"
United States
Anne
The price is AED 512
AED 584 total
includes taxes & fees
25 Feb - 26 Feb
Loudoun Valley Manor
Exterior

Antietam Overlook Farm

Antietam Overlook Farm
3.5 star property
Keedysville
10.0 out of 10, Exceptional, (221 reviews)
"My boyfriend and I really enjoyed our stay at Antietam Overlook Farm! We had never stayed at a bed and breakfast prior to this trip which made it a cool and unique experience to have our first experience here. "
United States
Emily
The price is AED 672
AED 826 total
includes taxes & fees
27 Jan - 28 Jan
Antietam Overlook Farm
Front of property

Hollerstown Hill Bed and Breakfast

Hollerstown Hill Bed and Breakfast
3.5 star property
Frederick
9.6 out of 10, Exceptional, (96 reviews)
"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 841
AED 891 total
includes taxes & fees
26 Jan - 27 Jan
Hollerstown Hill Bed and Breakfast
Front of property

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (441 reviews)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 471
AED 533 total
includes taxes & fees
28 Jan - 29 Jan
The Carriage Inn B&B
Front of property

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (96 reviews)
"The breakfast was fabulous and the room great "
United States
MICHEL
The price is AED 703
AED 802 total
includes taxes & fees
27 Jan - 28 Jan
Stone Manor Boutique Inn
Exterior

Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (76 reviews)
"The hostess and her husband were friendly and made us feel very welcome! Breakfast was scrambled eggs with fruit and was nice."
United States
Ron
The price is AED 569
AED 638 total
includes taxes & fees
26 Jan - 27 Jan
Cantuta Inn
Interior 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 reviews)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
The price is AED 1,433
AED 1,633 total
includes taxes & fees
7 Feb - 8 Feb
The Inn at Grass Roots Hill
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

Hillside Inn & Suite

Hillside Inn & Suite

10/10 Excellent
"Easy check in, this is my 2nd time staying here the staff is so friendly, the place is clean and the bed comfortable, I nice extra is that the room has a very comfortable chair and ottoman so you can put your feet up and relax, I have saved this Hotel in my favorites and next time I make a trip down south I will make this my layover "
Colleen 1-night trip
Posted 4 days ago
Hillside Inn & Suite

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. Stone Manor Boutique Inn: 6 rooms. 15.6 mi (25.2 km) from the heart of downtown. Enjoy the free full breakfast and winery. Lily Garden Bed and Breakfast: 2 rooms. Located 13.2 mi (21.3 km) from the core of Middletown.
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.