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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

B&B in Middletown

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (61)
"It is set in a quiet small community. The grounds are beautiful and restful. There is a lovely patio. It is a haven for escape from the busy world. "
The price is SAR 811
SAR 958 total
includes taxes & fees
17 Jun - 18 Jun
Cromwell Manor Inn
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (118)
"Lovely BnB, helpful and friendly staff, convenient location with many attractions within a short driving distance."
Borland House Inn
Villa Verde BB Greenwood Lake NY
Skiing

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (5)
"Eva was a gracious host. The breakfast was very good. "
The price is SAR 739
SAR 911 total
includes taxes & fees
22 Jun - 23 Jun
Villa Verde BB Greenwood Lake NY
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (113)
"Very nice accommodations & staff."
The price is SAR 516
SAR 584 total
includes taxes & fees
17 Jun - 18 Jun
Tin Brook Bed & Breakfast
Buck's Homestead B&B
Front of property

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (51)
"Fantastic trip to Montgomery made even better by staying here. Joan was so kind and accommodating, and made such a delicious breakfast every morning. We felt very at home, it was like staying with family & we were sad to leave! Our room was very comfortable, the location is beautiful, as is the house, with such an interesting history. Watching the birds, chipmunks and groundhogs was an added bonus! We can't say enough about what a great stay we had, we would come back in a heartbeat."
Buck's Homestead B&B
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (309)
"Great location, attentive owner, comfortable bed, and the best breakfast! If we come to the area again will definitely book another stay."
The price is SAR 751
SAR 861 total
includes taxes & fees
17 Jun - 18 Jun
Alpine Haus Bed & Breakfast Inn
The Dominion House Bed & Breakfast
Exterior

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (224)
"The house and accommodations are beautifully appointed, the hosts were helpful and engaging and the breakfasts were outstanding - make sure you request Susie’s fabulous scones! "
The price is SAR 807
SAR 913 total
includes taxes & fees
18 Jun - 19 Jun
The Dominion House Bed & Breakfast
Stagecoach Inn
Roosevelt #3, 1 King Bed | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (76)
"Unique and quaint inn with lots to offer or do nothing at all except relax!"
The price is SAR 920
SAR 1,132 total
includes taxes & fees
30 Jun - 1 Jul
Stagecoach Inn
John H Wallace House
Outdoor wedding area

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (8)
"The John H Wallace House is the oldest historic house in Milford. Our host was friendly and knowledgeable and gave us a tour of the whole beautiful house!! The house has been newly renovated!! The bathroom and shower were gorgeous! The breakfast was outstanding and even had homemade scones, clotted cream and lemon curd served on beautiful china!! It was truly a home away from home! "
The price is SAR 875
SAR 954 total
includes taxes & fees
17 Jun - 18 Jun
John H Wallace House
Caldwell House Bed & Breakfast
Room | 1 bedroom, premium bedding, pillowtop beds, individually decorated

Caldwell House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (473)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House Bed & Breakfast
Columbus Hotel
Economy Studio | 1 bedroom, individually decorated, individually furnished, desk

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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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. Borland House Inn: 5 rooms. Situated 11.1 mi (17.9 km) from the heart of Middletown. Enjoy the free full breakfast and deli. 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.