Photo by Vincent Ramundo

Find a Bed and Breakfast in Middletown from CA $157

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Middletown B&B

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (58)
"Awesome place. Very quiet"
The price is CA $272
CA $308 total
includes taxes & fees
May 7 - May 8
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 CA $277
CA $317 total
includes taxes & fees
May 1 - May 2
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 CA $157
CA $178 total
includes taxes & fees
May 1 - May 2
Borland House 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."
The price is CA $190
CA $215 total
includes taxes & fees
May 1 - May 2
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 CA $281
CA $345 total
includes taxes & fees
May 5 - May 6
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 CA $297
CA $324 total
includes taxes & fees
May 1 - May 2
John H Wallace House
Stagecoach Inn
Roosevelt #3, 1 King Bed

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 CA $346
CA $426 total
includes taxes & fees
May 1 - May 2
Stagecoach Inn
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
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 CA $297
CA $336 total
includes taxes & fees
May 5 - May 6
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

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)
"Celebrated my husbands 50th birthday and the property was perfect!"
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"Great place and host!"
The price is CA $232
CA $385 total
includes taxes & fees
May 1 - May 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Cabin with Sauna & Firepit!
Outdoor dining

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (24)
"Excellent "
Cozy Cabin with Sauna & Firepit!
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

What is the nightly rate for a Bed and Breakfast in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from CA $157 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.
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.