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Check prices for these dates

Next weekend
Mar 13 - Mar 15
In two weeks
Mar 20 - Mar 22
In one month
Apr 3 - Apr 5
In two months
May 1 - May 3

Our top choices for Middletown bed & breakfast

Individually decorated, individually furnished, desk, iron/ironing board

Columbus Hotel

Columbus Hotel
3.0 star property
Middletown
6.0 out of 10, (6 reviews)
"21 minutes ago on Google It's a family owned and operated hotel. Norman was kind, communicative and thorough. Keyless entry made checking in super easy. We had a business suite, which is basically a studio apartment. Kitchen , bathroom, bed/living space was clean and neat having a really nice modern clean aesthetic. There was even a candle left for us to enjoy. Overall was a very pleasant stay! Very grateful. "
United States
Diane
Columbus Hotel
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (153 reviews)
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
United States
wendy
Borland House Inn
Outdoor wedding area

John H Wallace House

John H Wallace House
4.0 star property
Milford
10.0 out of 10, Exceptional, (15 reviews)
"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
The price is ￥26,582
￥28,974 total
includes taxes & fees
Mar 12 - Mar 13
John H Wallace House
Front of property

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (16 reviews)
"Excellent stay and delicious breakfast. Clear communication!"
United States
Linda
The price is ￥28,648
￥32,407 total
includes taxes & fees
Mar 10 - Mar 11
Villa Verde BB Greenwood Lake NY
Exterior

Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
3.0 star property
Vernon
9.2 out of 10, Wonderful, (330 reviews)
"We had a great weekend stay at Alpine! The caretaker, Anil was so hospitable! We will definitely be back soon!"
United States
Krystal
The price is ￥31,454
￥36,054 total
includes taxes & fees
Mar 5 - Mar 6
Alpine Haus Bed & Breakfast Inn
Restaurant

Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
"We only stayed one night, but it was very comfortable and the staff was friendly. "
United States
Kathryn
The price is ￥44,311
￥54,560 total
includes taxes & fees
Mar 5 - Mar 6
Stagecoach Inn
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (95 reviews)
"Great stay!"
United States
Amrita
Cromwell Manor Inn
Exterior

Pine Brook Manor

Pine Brook Manor
2.0 star property
Sparrow Bush
The price is ￥33,215
￥76,715 total
includes taxes & fees
Mar 5 - Mar 6
Pine Brook Manor
Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
"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
The price is ￥33,813
￥38,251 total
includes taxes & fees
Mar 9 - Mar 10
The Dominion House Bed & Breakfast
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

Tru by Hilton Middletown

Tru by Hilton Middletown

10/10 Excellent
"Property was bright and clean. Staff was friendly and very accommodating "
Tanya 2-night trip
Posted 1 day ago
Tru by Hilton Middletown

Find out more about Middletown

Middletown B&B information

Number of reviews
848
Accommodation
12 B&B
Lowest Price
￥28,974
Highest Price
￥76,715

Frequently asked questions

Searching for B&Bs in Middletown?
If you want to find an accommodation with fewer rooms than a hotel and a more personalized environment, a B&B may be the perfect thing for your trip to Middletown. While you're enjoying your trip to Middletown, you might want to explore the theater scene by catching a show at Paramount Theatre.
Why choose a B&B over a traditional hotel room?
With attentive service, opportunities to meet other guests, and of course a scrumptious breakfast, B&Bs all have a unique environment.
What are the best B&Bs in Middletown?
Below are some B&Bs in the area: Columbus Hotel: 15 rooms. 0.5 mi (0.8 km) from the heart of Middletown. Enjoy the unique décor and onsite dining. Villa Verde BB Greenwood Lake NY: 2 rooms. 16.8 mi (27.1 km) from the downtown core. Enjoy the free full breakfast and unique décor. Alpine Haus Bed & Breakfast Inn: 10 rooms. Situated 18 mi (29 km) from the heart of Middletown. Enjoy the arcade game room and library. Borland House Inn: 5 rooms. 11.1 mi (17.9 km) from the heart of downtown. Enjoy the free full breakfast and deli.
What's the best time of year to book my B&B in Middletown?
When you're dreaming of a trip 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 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Middletown are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Middletown?
Travelers enjoy Middletown for its restaurants and shopping. When you want to spend some time in the great outdoors, Thomas Bull Memorial Park and Highland Lake are some notable spots. You might put Paramount Theatre and Orange County Fair Speedway 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 Stewart Intl. Airport (SWF), which is located 17.8 mi (28.7 km) away from the heart of the city. If you'd like to venture out around the area, you may want to rent a car for your trip.

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