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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Middletown

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.6 out of 10, Exceptional, (81)
"Lovely spot and wonderful innkeeper hosts."
The price is AED 913
AED 1,079 total
includes taxes & fees
6 Oct - 7 Oct
Cromwell Manor Inn
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (121)
"Everything was perfect including great breakfast"
Tin Brook Bed & Breakfast
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (127)
"The room was great. Comfortable bed, clean and the breakfasts were great. I would highly recommend it. Brianna and Victoria are awesome hosts and the house is really cool. "
Borland House Inn
Villa Verde BB Greenwood Lake NY
Exterior

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (7)
"Eva was a gracious host. The breakfast was very good. "
The price is AED 746
AED 917 total
includes taxes & fees
1 Oct - 2 Oct
Villa Verde BB Greenwood Lake NY
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (317)
"The host is lovely and wanted everyone to feel comfortable. Delicious breakfast served. Wonderful bed and hot showers. "
The price is AED 735
AED 842 total
includes taxes & fees
1 Oct - 2 Oct
Alpine Haus Bed & Breakfast Inn
Buck's Homestead B&B
Front of property

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (61)
"Very comfortable stay"
Buck's Homestead B&B
Caldwell House Bed & Breakfast
Room | 14 bedrooms, premium bedding, pillowtop beds, individually decorated

Caldwell House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (474)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House Bed & Breakfast
The Dominion House Bed & Breakfast
Superior Double Room, Ensuite (Primrose) | Miscellaneous

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (229)
"Amazing hospitality,"
The price is AED 790
AED 893 total
includes taxes & fees
2 Oct - 3 Oct
The Dominion House Bed & Breakfast
Stagecoach Inn
Restaurant

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (78)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
The price is AED 1,194
AED 1,470 total
includes taxes & fees
2 Oct - 3 Oct
Stagecoach Inn
John H Wallace House
Outdoor wedding area

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (9)
"Great location adorable house lovely nice sized rooms brand new beds and bathrooms. Super friendly owners going above and beyond to be helpful lovely breakfast highly recommend staying here in this ideal little town in a historic home with all the modern conveniences "
The price is AED 726
AED 792 total
includes taxes & fees
1 Oct - 2 Oct
John H Wallace House
Columbus Hotel
Economy Studio | Individually decorated, individually furnished, desk, iron/ironing board

Columbus Hotel

3.0 star property
6.0 out of 10, (6)
"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. "
Columbus Hotel
Saint Huberts Lodge
Billiards

Saint Huberts Lodge

3.5 star property
9.0 out of 10, Wonderful, (44)
"Our stay was rather disappointing. The property seems neglected. Some lightbulbs in the bathroom were not working . The coffee maker was really filthy inside. Instead of breakfast we were offered some packaged pastry from a gas station. Plus, there were a bunch of insects in the room. There was no drinking water in the property we ended up driving to get water. I don’t understand they can charge so much money "
Saint Huberts Lodge
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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"Great for business stay "
Mark 1-night trip
Posted 2 days ago
Hampton Inn by Hilton Middletown

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 bar/lounge. Tin Brook Bed & Breakfast: 6 rooms. Situated 15.7 mi (25.3 km) from the heart of Middletown. Villa Verde BB Greenwood Lake NY: 2 rooms. 16.8 mi (27.1 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Alpine Haus Bed & Breakfast Inn: 10 rooms. Located 18 mi (29 km) from the core of Middletown. Enjoy the arcade game room and library.
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.