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Book Middletown Bed & Breakfast

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Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Middletown

Cromwell Manor Inn
Stately two-story house with a central entrance and columns, surrounded by a well-manicured lawn.

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (67)
"Very gracious innkeepers; great breakfast in a beautiful setting."
$247 nightly
The price is $292
Aug 19 - Aug 20
Total includes taxes and fees
Cromwell Manor Inn
Borland House Inn
Welcome to this charming two-story house with a welcoming front porch and beautifully manicured surroundings.

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (124)
"We loved our stay here! It was cozy, quiet, and the breakfast was amazing. The staff was wonderful at getting accomodations ready for our child before we arrived. Highly recommend for anyone who wants to enjoy a quiet and relaxing getaway within walking distance to shops and restaurants."
$190 nightly
The price is $215
Sep 5 - Sep 6
Total includes taxes and fees
Borland House Inn
Alpine Haus Bed & Breakfast Inn
Relax on the covered porch with comfortable seating and a small table for refreshments, surrounded by lush greenery.

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (313)
"The porch outside our room was a great spot to sit and enjoy the beautiful view of the valley and surrounding hills at sunset."
$200 nightly
The price is $229
Aug 6 - Aug 7
Total includes taxes and fees
Alpine Haus Bed & Breakfast Inn
Villa Verde BB Greenwood Lake NY
Stroll along the garden pathway to the inviting pool area surrounded by lush greenery and beautifully trimmed bushes and trees.

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. "
$225 nightly
The price is $255
Aug 11 - Aug 12
Total includes taxes and fees
Villa Verde BB Greenwood Lake NY
Tin Brook Bed & Breakfast
Stroll up to this charming home, featuring a cozy front porch and a beautifully manicured lawn.

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (115)
"Very nice accommodations & staff."
$138 nightly
The price is $156
Aug 6 - Aug 7
Total includes taxes and fees
Tin Brook Bed & Breakfast
Buck's Homestead B&B
Stroll through the serene grounds of this charming two-story home, surrounded by mature trees and a beautifully manicured lawn.

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (58)
"Very comfortable stay"
Buck's Homestead B&B
The Dominion House Bed & Breakfast
Stroll through the serene garden, surrounded by lush plants and a soothing fountain, with a charming gazebo in the distance.

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (227)
"Amazing hospitality,"
$215 nightly
The price is $243
Aug 11 - Aug 12
Total includes taxes and fees
The Dominion House Bed & Breakfast
John H Wallace House
Stroll through a serene garden with a central water feature, surrounded by lush plants and a tiered stone structure.

John H Wallace House

4.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful B&B updated with modern conveniences while maintaining some of the original parts of the home. Joh and Linda were very very nice hosts. "
$218 nightly
The price is $238
Aug 10 - Aug 11
Total includes taxes and fees
John H Wallace House
Stagecoach Inn
Enjoy meals in this dining area with high ceilings, large windows, and a door leading to an outdoor space.

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (76)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
$209 nightly
The price is $257
Aug 6 - Aug 7
Total includes taxes and fees
Stagecoach Inn
Columbus Hotel
Relax in a serene bedroom with a four-poster bed, minimalist design, and a large window.

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
Caldwell House Bed & Breakfast
Classic hotel room with a large bed, four-poster bed frame, and a fireplace.

Caldwell House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (473)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House Bed & Breakfast
Saint Huberts Lodge
Enjoy a game of pool in this stylish room with a pool table, ornate chandelier, and beautiful artwork.

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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"The room was in quiet area no kids making noise thank you will request same area next time I visit"
Denise 1-night trip
Posted 2 days ago
Hampton Inn Harriman Woodbury

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 $156 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.