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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 13 B&B in Middletown with updated reviews, rates, and availability.

Borland House Inn
Front of property

Borland House Inn

3.0 star property
9.0 out of 10, Wonderful, (103)
"Quaint house"
The price is AED 335
AED 378 total
includes taxes & fees
2 Mar - 3 Mar
Borland House Inn
Alpine Haus Bed & Breakfast Inn
Exterior

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (305)
"This hotel is a five-minute walk from the Mountain Creek resort. Breakfast was really delicious. The owner was very nice and friendly. Told us stories about his life while we had our breakfast. We will definitely come back again."
The price is AED 735
AED 842 total
includes taxes & fees
24 Feb - 25 Feb
Alpine Haus Bed & Breakfast Inn
Cromwell Manor Inn
Reception

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (55)
"It was a beautiful stay, had everything you could think of for fun and convience, and the staff is very friendly. "
Cromwell Manor Inn
Stagecoach Inn
Room

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (75)
"Great find!!"
The price is AED 863
AED 1,063 total
includes taxes & fees
26 Feb - 27 Feb
Stagecoach Inn
Villa Verde BB Greenwood Lake NY
Beach

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (1)
"Truly wonderful host and property. Incredible location and impeccable residence- our experience was amazing in every way. We felt incredibly accommodated while also enjoying all the privacy needed within our beautiful suite. My partner was celebrating her 30th birthday- our host went above and beyond to make the trip truly special. She even accommodated her vegan dietary requests for breakfast! Speaking of- the breakfast was incredible- one of the best breakfast experiences I've ever enjoyed....
The price is AED 684
AED 847 total
includes taxes & fees
8 Mar - 9 Mar
Villa Verde BB Greenwood Lake NY
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 AED 790
AED 893 total
includes taxes & fees
26 Feb - 27 Feb
The Dominion House Bed & Breakfast
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (110)
"Very nice small town bed and breakfast. We didn't take advantage of all the amenities."
Tin Brook Bed & Breakfast
John H Wallace House
Front of property

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (1)
"What an incredible experience! My fiancé and I had the pleasure of staying at the John H Wallace House, and from start to finish, it was nothing short of amazing. The hospitality was exceptional, making us feel right at home. The house itself is a perfect blend of history and comfort, thoughtfully decorated with a mix of antique and modern touches. Every detail reflects care, making the space feel both cozy and impeccably clean. We loved learning about the rich history of the house and town,...
The price is AED 604
AED 659 total
includes taxes & fees
16 Mar - 17 Mar
John H Wallace House
Caldwell House Bed & Breakfast
Room

Caldwell House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (472)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House 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, (47)
"Joa's place is a delightful 1830 farmhouse on a quiet, yet convenient road. My suite was cozy, comfortable and private, decorated with authentic antiques which added to the charm."
Buck's Homestead B&B
Columbus Hotel
Room

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
Exterior

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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Other property types in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Exterior

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (70)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is AED 617
AED 900 total
includes taxes & fees
24 Feb - 25 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (39)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
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.

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, Highland Lakes State Park and Thomas Bull Memorial Park are perfect spots to get in some fresh air and greenery.
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. 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.
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 Highland Lakes State 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.