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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Middletown bed & breakfast

Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is AED 988
AED 1,080 total
includes taxes & fees
20 Jan - 21 January 2026
Glen Gordon Manor
Porch
Gay Street Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is AED 1,319
AED 1,421 total
includes taxes & fees
22 Jan - 23 January 2026
Gay Street Inn
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!"
David 1-night trip
Posted 8 hours ago
Comfort Inn & Suites Winchester

Frequently asked questions

Searching for B&Bs in Middletown?
If you're looking for something a little quirkier than your standard hotel, a stay at a bed and breakfast could be a great option for your trip. While you're enjoying your trip to Middletown, you might want to explore the theater scene by catching a show at Wayside Theater.
How do you know if a B&B is a good option for you?
Every B&B has a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Middletown?
Here is a B&B that guests like in the surrounding area: Glen Gordon Manor: 8 rooms. 16.9 mi (27.2 km) from the heart of Middletown. Enjoy the free full breakfast and 24-hour fitness center.
When should I stay at a B&B in Middletown?
When you're dreaming of a escape to Middletown, be sure to take into account the year-round temperatures. 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 43 inches.
What is there to do in Middletown?
If you like to experience a new place through your taste buds, you'll be sure to enjoy Middletown for its bars and restaurants. When you want to spend some time in the great outdoors, Shenandoah River and Cedar Creek and Belle Grove National Historical Park are some notable spots. You might put Belle Grove Plantation and Wayside Theater on your list if you want to see more of the area.
How can I get to and around Middletown?
You can plan your excursions in and around Middletown ahead of time with these transportation options. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 30.4 mi (48.9 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.