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Check prices for these dates

Next weekend
3 Apr - 5 Apr
In two weeks
10 Apr - 12 Apr
In one month
24 Apr - 26 Apr
In two months
22 May - 24 May

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
Front of property

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (157 reviews)
"Our room was beautiful and well maintained and spotlessly clean. I did not realize before we came to the hotel that the bathroom was out in the hall, not en suite. "
United States
Andrea
The price is SAR 385
SAR 448 total
includes taxes & fees
29 Mar - 30 Mar
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, (16 reviews)
"The house is well located and Eileen was a great host."
United States
Donna
The price is SAR 621
SAR 677 total
includes taxes & fees
29 Mar - 30 Mar
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, (18 reviews)
"Lovely property, owner and food! A gem!"
United States
Riley
The price is SAR 798
SAR 903 total
includes taxes & fees
27 Mar - 28 Mar
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)
"Really nice "
United States
Jennifer
The price is SAR 751
SAR 861 total
includes taxes & fees
26 Mar - 27 Mar
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (96 reviews)
"Great stay!"
United States
Amrita
The price is SAR 867
SAR 1,024 total
includes taxes & fees
30 Mar - 31 Mar
Cromwell Manor 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 SAR 1,058
SAR 1,302 total
includes taxes & fees
26 Mar - 27 Mar
Stagecoach Inn
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 SAR 807
SAR 913 total
includes taxes & fees
6 Apr - 7 Apr
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

Resorts World Catskills Casino

Resorts World Catskills Casino

8/10 Good
"My only suggestion is a microwave in the rooms. "
Charlene 1-night trip
Posted 1 day ago
Resorts World Catskills Casino

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. Alpine Haus Bed & Breakfast Inn: 10 rooms. 18 mi (29 km) from the downtown core. Enjoy the arcade game room and library. Villa Verde BB Greenwood Lake NY: 2 rooms. Situated 16.8 mi (27.1 km) from the heart of Middletown. Enjoy the free full breakfast and unique décor. Borland House Inn: 5 rooms. Located 11.1 mi (17.9 km) from the core of Middletown. 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, Highland Lake and Thomas Bull Memorial Park 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.