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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 12 B&B in Middletown with updated reviews, rates, and availability.

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (60)
"Staff was extremely helpful and friendly. Pleasant stay and located next to Jones Farm for lunch and snacks. Very scenic location. "
The price is AED 740
AED 838 total
includes taxes & fees
11 May - 12 May
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, (308)
"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 AED 735
AED 842 total
includes taxes & fees
7 May - 8 May
Alpine Haus Bed & Breakfast Inn
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Perfect stay "
The price is AED 697
AED 788 total
includes taxes & fees
9 May - 10 May
Borland House Inn
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (112)
"Very lovely hosts and great overall service!"
The price is AED 505
AED 571 total
includes taxes & fees
7 May - 8 May
Tin Brook Bed & Breakfast
Villa Verde BB Greenwood Lake NY
Skiing

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (2)
"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 746
AED 917 total
includes taxes & fees
20 May - 21 May
Villa Verde BB Greenwood Lake NY
John H Wallace House
Outdoor wedding area

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (5)
"The service was very personal and it's the sort of thing you can't replicate. "
The price is AED 790
AED 861 total
includes taxes & fees
22 May - 23 May
John H Wallace House
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 AED 1,010
AED 1,244 total
includes taxes & fees
7 May - 8 May
Stagecoach Inn
Caldwell House Bed & Breakfast
Room | 14 bedrooms, premium bedding, pillowtop beds, individually decorated

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
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
8 May - 9 May
The Dominion 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)
"Cute farmhouse with great service. Breakfast was delicious and we enjoyed visiting with the owner. I would gladly stay again. "
Buck's Homestead B&B
Columbus Hotel
Economy Studio | Individually decorated, individually furnished, desk, iron/ironing board

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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Other property types in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

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

9.0 out of 10, Wonderful, (73)
"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!
Cozy Cabin with Sauna & Firepit!
Outdoor dining

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (25)
"Excellent "
Cozy Cabin with Sauna & Firepit!
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (288)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is AED 1,429
AED 1,870 total
includes taxes & fees
12 May - 13 May
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
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, 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 onsite dining. Borland House Inn: 5 rooms. 11.1 mi (17.9 km) from the downtown core. 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. Tin Brook Bed & Breakfast: 6 rooms. Located 15.7 mi (25.3 km) from the core of Middletown.
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.