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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Middletown

Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
$259 nightly
The price is $283
Aug 17 - Aug 18
Total includes taxes and fees
Glen Gordon Manor
Gay Street Inn
Interior detail

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (33)
"Great place to stay in Washington VA to walk to inn at little Washington, patty O's (6 min walk), bakery, chocolates and rural landscape! "
$359 nightly
The price is $387
Aug 21 - Aug 22
Total includes taxes and fees
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"They had oatmilk and oatmeal which was fantastic for vegans!"
Susan 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Winchester

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $283 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.
When is the best time to book a Bed & Breakfast in Middletown?
The best time to book a B&B in Middletown is from June to September, which marks the peak season for travelers seeking a vibrant getaway. During these summer months, visitors flock to the area to enjoy the warm weather, allowing for a plethora of outdoor activities such as hiking, biking, and stunning beach outings. The average temperatures hover between the mid-70s to low 80s Fahrenheit, creating an inviting climate for exploring the region's natural beauty and attractions.

July stands out as the most popular month, bustling with energy as both locals and tourists come together to celebrate various summer festivals and events. This lively atmosphere enhances the overall experience, making it an ideal time for those who thrive in a social setting.

For travelers looking for a more budget-friendly option, consider visiting in December. This month offers a unique charm, as the region transforms with holiday festivities, cozy accommodations, and scenic winter landscapes. While the weather can be cooler, with temperatures dipping into the low 40s Fahrenheit, the serene ambiance allows for peaceful explorations and intimate moments.
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.