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Book Middletown Bed & Breakfast

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B&B in Middletown

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.6 out of 10, Exceptional, (80)
"Lovely spot and wonderful innkeeper hosts."
$201 nightly
The price is $238
Sep 28 - Sep 29
Total with taxes and fees
Cromwell Manor Inn
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (121)
"Everything was perfect including great breakfast"
Tin Brook Bed & Breakfast
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (127)
"The room was great. Comfortable bed, clean and the breakfasts were great. I would highly recommend it. Brianna and Victoria are awesome hosts and the house is really cool. "
$114 nightly
The price is $129
Sep 28 - Sep 29
Total with taxes and fees
Borland House Inn
Villa Verde BB Greenwood Lake NY
Exterior

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (7)
"Eva was a gracious host. The breakfast was very good. "
$223 nightly
The price is $252
Oct 26 - Oct 27
Total with taxes and fees
Villa Verde BB Greenwood Lake NY
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (317)
"The host is lovely and wanted everyone to feel comfortable. Delicious breakfast served. Wonderful bed and hot showers. "
$200 nightly
The price is $229
Sep 28 - Sep 29
Total with taxes and fees
Alpine Haus Bed & Breakfast Inn
Buck's Homestead B&B
Front of property

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (61)
"Very comfortable stay"
Buck's Homestead B&B
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, (474)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House Bed & Breakfast
The Dominion House Bed & Breakfast
Superior Double Room, Ensuite (Primrose) | Miscellaneous

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (229)
"Amazing hospitality,"
$215 nightly
The price is $243
Sep 29 - Sep 30
Total with taxes and fees
The Dominion House Bed & Breakfast
Stagecoach Inn
Restaurant

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (77)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
$325 nightly
The price is $400
Sep 28 - Sep 29
Total with taxes and fees
Stagecoach Inn
John H Wallace House
Outdoor wedding area

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (9)
"Great location adorable house lovely nice sized rooms brand new beds and bathrooms. Super friendly owners going above and beyond to be helpful lovely breakfast highly recommend staying here in this ideal little town in a historic home with all the modern conveniences "
$205 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
John H Wallace House
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. "
$221 nightly
The price is $251
Sep 27 - Sep 28
Total with taxes and fees
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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Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Very nice. Out if the way with beautiful views. One problem: no elevator for older guests, and the website did not mention it. Perhaps put them on the first floor? It was not easy hauling suitcases up and down the long flight of stairs. Another guest also commented on it. If we had known, we could have requested a first floor room "
Shirley L 1-night trip
Posted 23 hours ago
Overlook Lodge at Bear Mountain

Find out more about Middletown

Find out more about Middletown

Middletown B&B information

Number of reviews
901
Accommodation
12 B&B
Lowest Price
$129
Highest Price
$400

Frequently asked questions

What is the nightly rate for a B&B in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $129 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middletown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Middletown?
The best time to book a B&B in Middletown is during the vibrant summer months of June through August. This peak season attracts travelers eager to enjoy the area's warm weather and plethora of outdoor activities, such as hiking, biking, and exploring local parks. With temperatures typically ranging from the upper 70s to low 90s Fahrenheit, visitors can comfortably partake in sightseeing and outdoor adventures, all while soaking in the region's natural beauty.

July stands out as the most popular month to visit, when the community comes alive with festivals and events that celebrate the local culture. This lively atmosphere makes it an ideal time for those who appreciate a bustling environment filled with entertainment and opportunities to connect with fellow travelers.

If you're seeking a more budget-friendly experience, consider planning your visit in early fall, particularly in October. This month offers a lovely backdrop of autumn colors and a more relaxed pace, allowing you to enjoy the scenic trails and charming downtown without the crowds. The weather remains pleasant, typically in the 60s to 70s Fahrenheit, making it conducive for leisurely strolls and exploration.
What is the difference between a Middletown Bed and Breakfast and a hotel?
Every Middletown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Middletown B&Bs.

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