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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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 343
AED 388 total
includes taxes & fees
30 Jan - 31 Jan
Borland House Inn
Alpine Haus Bed & Breakfast Inn
Exterior

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (302)
"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 661
AED 758 total
includes taxes & fees
24 Jan - 25 Jan
Alpine Haus Bed & Breakfast Inn
Cromwell Manor Inn
Reception

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (54)
"This what exactly what I was looking for when I booked one night away. I am a single mom and all I wanted was one night of silence. The manor is so cozy and peaceful, I felt so safe and welcomed. And the breakfast was amazing. Will definitely be back for my next night away!"
The price is AED 732
AED 828 total
includes taxes & fees
31 Jan - 1 Feb
Cromwell Manor Inn
Stagecoach Inn
Room

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (74)
"Great find!!"
The price is AED 804
AED 990 total
includes taxes & fees
25 Jan - 26 Jan
Stagecoach 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 AED 790
AED 893 total
includes taxes & fees
27 Jan - 28 Jan
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
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 727
AED 896 total
includes taxes & fees
24 Jan - 25 Jan
Villa Verde BB Greenwood Lake NY
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
John H Wallace House
Front of property

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (1)
"An amazing stay at John Wallace House! The property has been completely renovated for comfort and key period design. I can’t say enough about the staff John and Linda, they are so friendly and have created a warm and inviting space throughout the house. Room was , clean and quiet and so relaxing! Breakfast was all home made fresh and delicious. John and Linda have created something very special, will definitely stay again."
The price is AED 672
AED 732 total
includes taxes & fees
26 Jan - 27 Jan
John H Wallace House
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
Danskammer House
Front of property

Danskammer House

3.0 star property
9.8 out of 10, Exceptional, (82)
"The owners did masterful work restoring this home yet paid so much attention in providing up-to-date amenities that people have come to expect. Every convenience was thought of and there were wonderful treats and surprises at every turn. I particularly enjoyed their love of the Hudson River School and all of the lovely artwork represented from room to room. Local history is honored in the house and their knowledge of it is vast. "
Danskammer House
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

Cottage Suites
Room

Cottage Suites

3.0 star property
8.0 out of 10, Very Good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
Royal Garden Main Cabin
Bathroom

Royal Garden Main Cabin

9.6 out of 10, Exceptional, (4)
"ABSOLUTELY BEAUTIFUL!!! Its was a treat staying here. Its out in the country. Its called a cabin but its more of a house. The bedrooms were perfect and the beds were comfy. The property had a pond, and a fire pit. We seen 3 deer as we were pulling into the driveway. ABSOLUTELY RECOMMEND THIS RENTAL!!"
Royal Garden Main Cabin
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, (106)
"Great place and host!"
The price is AED 617
AED 896 total
includes taxes & fees
24 Jan - 25 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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 bar/lounge. Borland House Inn: 5 rooms. 11.1 mi (17.9 km) from the downtown core. Enjoy the free full breakfast and deli. Alpine Haus Bed & Breakfast Inn: 10 rooms. 18 mi (29 km) from the heart of downtown. Enjoy the arcade game room and library. Stagecoach Inn: 5 rooms. Located 6.1 mi (9.9 km) from the core of Middletown. Enjoy the soaking bathtubs 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 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.