Photo by Vincent Ramundo

Search B&B in Middletown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

B&B in Middletown

Exterior detail
Borland House Inn

Borland House Inn

3.0 star property
Montgomery
9.2 out of 10, Wonderful, (142)
"Beautiful, quaint and comfy."
United States
Suzanne
Borland House Inn
Outdoor wedding area
John H Wallace House

John H Wallace House

4.0 star property
Milford
10.0 out of 10, Exceptional, (12)
"Incredible breakfast, charming room, our hosts treated us very well, full tour of house before other guests arrived, easy to find, fabulous scones."
United States
Maryanne
The price is AED 599
AED 653 total
includes taxes & fees
16 Nov - 17 Nov
John H Wallace House
Exterior
Cromwell Manor Inn

Cromwell Manor Inn

4.0 star property
Cornwall
9.6 out of 10, Exceptional, (87)
"This is a beautiful property. The family that runs it is lovely. And the breakfast is amazing. This is the place to stay!"
United States
Laura
The price is AED 785
AED 927 total
includes taxes & fees
4 Dec - 5 Dec
Cromwell Manor Inn
Terrace/patio
Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn

3.0 star property
Vernon
9.2 out of 10, Wonderful, (323)
"Warm, comfortable experience "
United States
Sarahlee
The price is AED 735
AED 842 total
includes taxes & fees
15 Nov - 16 Nov
Alpine Haus Bed & Breakfast Inn
Restaurant
Stagecoach Inn

Stagecoach Inn

3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
"Comfortable, old inn with nice clean rooms and very friendly staff."
United States
Andrew
The price is AED 900
AED 1,108 total
includes taxes & fees
16 Nov - 17 Nov
Stagecoach Inn
Exterior
Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY

4.0 star property
Monroe
10.0 out of 10, Exceptional, (12)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is AED 684
AED 847 total
includes taxes & fees
30 Nov - 1 Dec
Villa Verde BB Greenwood Lake NY
Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Amazing hospitality,"
United States
Benedicto
The price is AED 790
AED 893 total
includes taxes & fees
17 Nov - 18 Nov
The Dominion House Bed & Breakfast
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"🙂"
Jared 1-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain

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.