Photo by Stephanie Sutton

Find a Bed and Breakfast in Middletown from CA $300

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Browse Select Middletown B&B

Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (81)
"Great experience. Beautiful site. "
The price is CA $300
CA $328 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Glen Gordon Manor
Gay Street Inn
Porch

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (31)
"Drew was a great host and was shared options for dining locally and understands how a first impression can set the tone of the stay. His attitude was very appreciated."
The price is CA $501
CA $540 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Gay Street Inn
Holliday House Strasburg
Luxury Room, 1 Queen Bed (Shared bathroom) | Room amenity

Holliday House Strasburg

3.5 star property
9.4 out of 10, Exceptional, (19)
"The property is very pretty and well-kept, conveniently located on the historic main street, the neighborhood is very charming."
Holliday House Strasburg
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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Other property types in Middletown

Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (162)
"It's the perfect cozy place for two for Thanksgiving. The indoor fireplace has plenty of firewood, and the outdoor firepit has a grill plate, perfect for making smores. We started our mornings having coffee in the hot tub. We will stay here again! "
Secluded, Cozy Cottage in the Shenandoah Valley
Mountain Views, River Frontage & HotTub + Country!
Outdoor spa tub

Mountain Views, River Frontage & HotTub + Country!

10.0 out of 10, Exceptional, (22)
"Stay was great. The cabin was clean and cozy. Communications w property management was great. The walk to the river was beautiful, and close The view of the mountains was awesome. 5/5 stay. "
Mountain Views, River Frontage & HotTub + Country!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
2 bedrooms, WiFi, bed sheets

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (293)
"The cabin is a very cozy getaway location, with a great view just out the window."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
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.

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 are some B&Bs 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 onsite spa services. Holliday House Strasburg: 3 rooms. Situated 5.1 mi (8.2 km) from the heart of Middletown. Enjoy the free cooked breakfast and in-room fireplace.
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 Cedar Creek Battlefield Foundation and Belle Grove Plantation 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.