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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

B&B in Middletown

Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (129)
"Unique experience, very comfortable, clean and quaint"
Borland House Inn
John H Wallace House
Outdoor wedding area

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (11)
"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 SAR 697
SAR 759 total
includes taxes & fees
2 Nov - 3 Nov
John H Wallace House
Villa Verde BB Greenwood Lake NY
Exterior

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (9)
"Eva was a gracious host. The breakfast was very good. "
The price is SAR 698
SAR 865 total
includes taxes & fees
2 Nov - 3 Nov
Villa Verde BB Greenwood Lake NY
Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.6 out of 10, Exceptional, (84)
"Very clean facility, very friendly innkeepers with excellent recommendations, excellent breakfast(made to order)"
The price is SAR 837
SAR 989 total
includes taxes & fees
10 Nov - 11 Nov
Cromwell Manor Inn
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 SAR 750
SAR 860 total
includes taxes & fees
12 Oct - 13 Oct
Alpine Haus Bed & Breakfast Inn
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 SAR 919
SAR 1,131 total
includes taxes & fees
5 Nov - 6 Nov
Stagecoach Inn
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 SAR 806
SAR 912 total
includes taxes & fees
14 Oct - 15 Oct
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

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"The staff was friendly and the room was clean. Dining (Mr Shanes) was good and convenient. Definitely would stay there again"
Erin 1-night trip
Posted 2 days ago
Best Western Hunt's Landing Hotel Matamoras/Milford

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. 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. Alpine Haus Bed & Breakfast Inn: 10 rooms. 18 mi (29 km) from the heart of downtown. 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.