Middletown B&B: Best Bed and Breakfast 2026

Q: 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 decor 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 snack bar/deli. Parkway House Goshen Boutique Bed & Breakfast : 5 rooms. 6.3 mi (10.1 km) from the city centre. Enjoy the private garden and unique decor. Tin Brook Bed & Breakfast : 6 rooms. Located 15.7 mi (25.3 km) from the core of Middletown.

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Our top choices for Middletown bed & breakfast

Tin Brook Bed & Breakfast

Walden

Laurie

includes taxes & fees

1 Jun - 2 Jun

Borland House Inn

Montgomery

"Did you ever want to experience what it would be like to stay at a bed in breakfast? Well this is the place to go! So quaint and cute! Located right in the heart of the town of Montgomery. Plenty of things to walk to and see in the area. Brianna the manager was wonderful. Very helpful and informative. The breakfast choices were delicious. Would definitely stay here again and recommend it to others."

roxanne

includes taxes & fees

1 Jun - 2 Jun

John H Wallace House

Milford

Donna

includes taxes & fees

1 Jun - 2 Jun

Villa Verde BB Greenwood Lake NY

Monroe

Peter

includes taxes & fees

1 Jun - 2 Jun

Cromwell Manor Inn

Cornwall

"This is a really lovely place! Some historic hotels/B&Bs are just historic and have seen better days. Not this place! We were only there for one night while on a road trip, but we would have enjoyed staying a few days longer. The manager greeted us warmly and made sure we enjoyed every minute of our stay. The house and grounds are beautiful. Our room was beautifully decorated and spotless, plus the bed was super comfy. After a long travel day we were happy to grab a pizza from a local restaurant...

barry

includes taxes & fees

7 Jun - 8 Jun

Parkway House Goshen Boutique Bed & Breakfast

Goshen

Daniel

includes taxes & fees

27 Jun - 28 Jun

Stagecoach Inn

Goshen

Kathryn

includes taxes & fees

7 Jun - 8 Jun

The Dominion House Bed & Breakfast

Chester

Anna

includes taxes & fees

3 Jun - 4 Jun

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Top Middletown Hotel Reviews

Super 8 by Wyndham Middletown

4/10 Poor

"Fix the roof on the main entrance. I had to push the door with my shoulder in order to get in. Door frame was loose. Vagrant near the door waiting to get in. Dog roaming the hallway."

The Crossroads Hotel, Newburgh

6/10 Okay

"Rooms have funky odor. Staff was great and changed me to another one but still felt the odd smell. There was lot of smoking and weed doing on the property and inside the hallways. The AC also not adjustable inside the room. It’s auto on and off. During the night time it would get hot and suddenly cold. No pool. No breakfast. Gym is there but not even water and proper weights are present. This property looks like had its glory once upon a time. But currently in a bad condition. It has lot of potential but needs the necessary up keeping. Needs lot of improvements."

Find out more about Middletown

Middletown B&B information

Number of reviews	666
Accommodation	13 B&B
Lowest Price	€133
Highest Price	€437

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?

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 decor 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 snack bar/deli. Parkway House Goshen Boutique Bed & Breakfast: 5 rooms. 6.3 mi (10.1 km) from the city centre. Enjoy the private garden and unique decor. 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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