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Search B&B in Middletown

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

Cromwell Manor Inn
Reception

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"Beautiful property, wonderful staff, amazing experience and highly recommend. "
The price is SAR 712
SAR 806 total
includes taxes & fees
20 Jan - 21 January 2025
Cromwell Manor Inn
Borland House Inn
Front of property

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Amazing in every possible way. The dinner was the best I've ever had."
The price is SAR 414
SAR 468 total
includes taxes & fees
5 Jan - 6 January 2025
Borland House 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 SAR 808
SAR 914 total
includes taxes & fees
26 Dec - 27 Dec
The Dominion House Bed & Breakfast
Stagecoach Inn
Room

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Best experience, i felt like i was in a hallmark movie or white Christmas. Staff was amazing they made me feel like i was a part of the family"
The price is SAR 748
SAR 920 total
includes taxes & fees
26 Dec - 27 Dec
Stagecoach Inn
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
Alpine Haus Bed & Breakfast Inn
Exterior

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (299)
"Arnil, A wonderful gentlemen and host. Enjoyed taking with him on many subjects. His culinary execution was high end . I will be visiting my new friend and BB again. Deborah "
The price is SAR 751
SAR 861 total
includes taxes & fees
24 Dec - 25 Dec
Alpine Haus Bed & Breakfast Inn
Villa Verde BB Greenwood Lake NY
Exterior

Villa Verde BB Greenwood Lake NY

3.0 star property
The price is SAR 744
SAR 841 total
includes taxes & fees
24 Dec - 25 Dec
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
Bathroom

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 SAR 773
SAR 843 total
includes taxes & fees
29 Dec - 30 Dec
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
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, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
28 Dec - 29 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Trails Head Tiny House
Updated picture of the exterior with the extended deck.

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is SAR 297
SAR 466 total
includes taxes & fees
24 Dec - 25 Dec
Trails Head Tiny 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.

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. Situated 11.1 mi (17.9 km) from the heart of Middletown. Enjoy the free full breakfast and deli. The Dominion House Bed & Breakfast: 3 rooms. 11.9 mi (19.1 km) from the heart of downtown. Enjoy the arcade game room and library. 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 Highland Lakes State Park are some notable spots. You might put Orange County Fair Speedway and Orange County Fairgrounds 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.