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Aug 8 - Aug 10
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B&B in Middletown

Cromwell Manor Inn
Stately two-story house with a central entrance and columns, surrounded by a well-manicured lawn.

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (67)
"Very gracious innkeepers; great breakfast in a beautiful setting."
The price is ￥32,693
￥38,618 total
includes taxes & fees
Aug 4 - Aug 5
Cromwell Manor Inn
Borland House Inn
Welcome to this charming two-story house with a welcoming front porch and beautifully manicured surroundings.

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (124)
"We loved our stay here! It was cozy, quiet, and the breakfast was amazing. The staff was wonderful at getting accomodations ready for our child before we arrived. Highly recommend for anyone who wants to enjoy a quiet and relaxing getaway within walking distance to shops and restaurants."
Borland House Inn
Alpine Haus Bed & Breakfast Inn
Relax on the covered porch with comfortable seating and a small table for refreshments, surrounded by lush greenery.

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (313)
"The porch outside our room was a great spot to sit and enjoy the beautiful view of the valley and surrounding hills at sunset."
The price is ￥29,480
￥33,791 total
includes taxes & fees
Aug 4 - Aug 5
Alpine Haus Bed & Breakfast Inn
Villa Verde BB Greenwood Lake NY
Stroll along the garden pathway to the inviting pool area surrounded by lush greenery and beautifully trimmed bushes and trees.

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 ￥28,433
￥35,114 total
includes taxes & fees
Aug 12 - Aug 13
Villa Verde BB Greenwood Lake NY
Tin Brook Bed & Breakfast
Stroll up to this charming home, featuring a cozy front porch and a beautifully manicured lawn.

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (114)
"Very nice accommodations & staff."
The price is ￥20,268
￥22,930 total
includes taxes & fees
Aug 4 - Aug 5
Tin Brook Bed & Breakfast
Buck's Homestead B&B
Stroll through the serene grounds of this charming two-story home, surrounded by mature trees and a beautifully manicured lawn.

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (58)
"Very comfortable stay"
Buck's Homestead B&B
The Dominion House Bed & Breakfast
Stroll through the serene garden, surrounded by lush plants and a soothing fountain, with a charming gazebo in the distance.

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (227)
"Amazing hospitality,"
The price is ￥31,691
￥35,851 total
includes taxes & fees
Aug 4 - Aug 5
The Dominion House Bed & Breakfast
John H Wallace House
Stroll through a serene garden with a central water feature, surrounded by lush plants and a tiered stone structure.

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful B&B updated with modern conveniences while maintaining some of the original parts of the home. Joh and Linda were very very nice hosts. "
The price is ￥29,550
￥32,209 total
includes taxes & fees
Aug 12 - Aug 13
John H Wallace House
Stagecoach Inn
Enjoy meals in this dining area with high ceilings, large windows, and a door leading to an outdoor space.

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (76)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
The price is ￥32,281
￥39,745 total
includes taxes & fees
Aug 5 - Aug 6
Stagecoach Inn
Columbus Hotel
Relax in a serene bedroom with a four-poster bed, minimalist design, and a large window.

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
Caldwell House Bed & Breakfast
Classic hotel room with a large bed, four-poster bed frame, and a fireplace.

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
Saint Huberts Lodge
Enjoy a game of pool in this stylish room with a pool table, ornate chandelier, and beautiful artwork.

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

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Always a great clean room"
Nicole 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 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.