Middletown B&B: Find a Bed and Breakfast 2026

Q: What are the best B&Bs in Middletown?

Here 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 decor and bar/lounge. Parkway House Goshen Family-Friendly Bed & Breakfast : 5 rooms. 6.3 mi (10.1 km) from the city centre. Enjoy the private garden and unique decor. Villa Verde BB Greenwood Lake NY : 2 rooms. Situated 16.8 mi (27.1 km) from the heart of Middletown. Enjoy the free full breakfast and snack bar/deli. Borland House Inn : 5 rooms. 11.1 mi (17.9 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Tin Brook Bed & Breakfast : 6 rooms. Located 15.7 mi (25.3 km) from the core of Middletown.

A lake surrounded by autumn-colored trees reflecting on the water.

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Our top choices for Middletown bed & breakfast

A modern bedroom with a four-poster bed, a desk, and a chair.

1. Columbus Hotel

Middletown

Donald

includes taxes & fees

11 Nov - 12 Nov

A large, two-story house with a wrap-around porch and multiple chimneys.

2. Parkway House Goshen Family-Friendly Bed & Breakfast

Goshen

Aakif

includes taxes & fees

12 Nov - 13 Nov

A large, two-story white house with a wrap-around porch and a small front garden.

3. The Dominion House Bed & Breakfast

Chester

"Amazing! The historic home sits on 40 acres of beautiful land inviting all guests to sit back and unwind. The beautiful home is decorated exquisitely and the hosts are warm and welcoming. If you are visiting West Point this place is a short drive away. It is nestled in a beautiful area making it an excellent option for a weekend get away-whether you are going to watch an Army football game or just want to get away, you will not be disappointed."

Sally

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a porch, a front door, and a small garden area with potted plants.

4. Borland House Inn

Montgomery

Kimberly

includes taxes & fees

10 Nov - 11 Nov

A dining area with brick flooring, large arched windows, and outdoor seating visible through the windows.

5. Stagecoach Inn

Goshen

Kathryn

includes taxes & fees

5 Dec - 6 Dec

6. John H Wallace House

Milford

David

includes taxes & fees

22 Nov - 23 Nov

A two-story house with a red front door, a chimney, and a well-maintained lawn.

7. Villa Verde BB Greenwood Lake NY

Monroe

Mark

includes taxes & fees

10 Nov - 11 Nov

A brick building with a covered patio area featuring outdoor seating and string lights.

8. Cromwell Manor Inn

Cornwall

Alice

includes taxes & fees

23 Nov - 24 Nov

A living room with a fireplace, a ceiling fan, a flat-screen TV, and a coffee table.

9. Tin Brook Bed & Breakfast

Walden

Michael

includes taxes & fees

10 Nov - 11 Nov

A small, single-story house with a steeply pitched roof, a front porch, and a staircase leading to the entrance.

10. Alpine Haus Bed & Breakfast Inn

Vernon

Debbie

includes taxes & fees

10 Nov - 11 Nov

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Top Middletown Hotel Reviews

Home2 Suites by Hilton Middletown

10/10 Excellent

"The room with two beds are very spacious and clean. I have stayed here 4 times this year!"

Tru by Hilton Middletown

10/10 Excellent

"I don’t often write reviews, but this one is WELL DESERVED!!!! - Polite, genuine, professional staff at every interaction from check in to check out - even my teenage son noticed and said, “wow, they are so polite here.” - So clean!!!!! - again, even a teenage boy noticed instantly when we opened the door to our room, “it smells really nice in here.” - Room was great, largest tv I’ve seen in a hotel room, had everything we needed, everything was well-stocked, like new and in perfect working order, even the USB charging ports! - Breakfast was perfect, just enough options to have anything you might want to start your day. - Coffee and tea available 24/7 in the lobby was an added nice touch, thank you! - Plenty of parking available, even on a Friday night when we arrived after 8:00pm to check in."

Find out more about Middletown

Middletown B&B information

Number of reviews	656
Accommodation	14 B&B
Lowest Price	S$156
Highest Price	S$530

Frequently asked questions

Searching for B&Bs in Middletown?

If you're looking for somewhere to stay with fewer rooms than a hotel and a more personalised environment, a bed and breakfast may be the perfect thing for your holiday to Middletown. While you're enjoying your trip to Middletown, you might want to explore the theatre scene by watching a show at Paramount Theatre.

Why choose B&Bs instead of traditional hotels?

With attentive service, opportunities to socialise with other guests and breakfast served on site, B&Bs offer a unique environment.

What are the best B&Bs in Middletown?

Here 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 decor and bar/lounge. Parkway House Goshen Family-Friendly Bed & Breakfast: 5 rooms. 6.3 mi (10.1 km) from the city centre. Enjoy the private garden and unique decor. Villa Verde BB Greenwood Lake NY: 2 rooms. Situated 16.8 mi (27.1 km) from the heart of Middletown. Enjoy the free full breakfast and snack bar/deli. Borland House Inn: 5 rooms. 11.1 mi (17.9 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Tin Brook Bed & Breakfast: 6 rooms. Located 15.7 mi (25.3 km) from the core of Middletown.

What's the best time of year to book my B&B in Middletown?

When you're dreaming of a stay in Middletown, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Middletown are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

What is there to do in Middletown?

Travellers 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 should 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 Newburgh, NY (SWF-Stewart Intl.), 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, consider renting a car to explore more sights.

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