Photo by Vincent Ramundo

Book Middletown Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Middletown bed & breakfast

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
$114 nightly
The price is $129
Dec 22 - Dec 23
Total with taxes and fees
Borland House Inn

John H Wallace House

John H Wallace House
4.0 star property
Milford
10.0 out of 10, Exceptional, (14)
"The John H. Wallace House is a welcoming and comfortable place to stay. Don’t hesitate to make a reservation to go there. "
United States
Barbara
$169 nightly
The price is $185
Dec 21 - Dec 22
Total with taxes and fees
John H Wallace House

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (13)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
$204 nightly
The price is $231
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Verde BB Greenwood Lake NY

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
$262 nightly
The price is $310
Dec 24 - Dec 25
Total with taxes and fees
Cromwell Manor Inn

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
"Unique and quaint inn with lots to offer or do nothing at all except relax!"
United States
Lorna
$235 nightly
The price is $289
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stagecoach Inn

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
$215 nightly
The price is $243
Dec 22 - Dec 23
Total with taxes and fees
The Dominion House Bed & Breakfast

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (326)
"Excellent experience, all the way around. Quiet and quaint, all the modern amenities, excellent host and service, hot water in the shower, beautiful room, bountiful, delicious breakfast."
United States
Robert
$200 nightly
The price is $229
Dec 21 - Dec 22
Total with taxes and fees
Alpine Haus Bed & Breakfast 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

Middletown B&B information

Number of reviews
667
Accommodation
12 B&B
Lowest Price
$129
Highest Price
$310

Frequently asked questions

What is the nightly rate for a B&B in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $129 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 B&B in Middletown?
The best time to book a B&B in Middletown is during the vibrant summer months of June through August. This peak season attracts travelers eager to enjoy the area's warm weather and plethora of outdoor activities, such as hiking, biking, and exploring local parks. With temperatures typically ranging from the upper 70s to low 90s Fahrenheit, visitors can comfortably partake in sightseeing and outdoor adventures, all while soaking in the region's natural beauty.

July stands out as the most popular month to visit, when the community comes alive with festivals and events that celebrate the local culture. This lively atmosphere makes it an ideal time for those who appreciate a bustling environment filled with entertainment and opportunities to connect with fellow travelers.

If you're seeking a more budget-friendly experience, consider planning your visit in early fall, particularly in October. This month offers a lovely backdrop of autumn colors and a more relaxed pace, allowing you to enjoy the scenic trails and charming downtown without the crowds. The weather remains pleasant, typically in the 60s to 70s Fahrenheit, making it conducive for leisurely strolls and exploration.
What is the difference between a Middletown Bed and Breakfast 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.

Explore a world of travel with Expedia