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

Search Bed and Breakfast in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Our top choices for Middletown bed & breakfast

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

1. Columbus Hotel

Columbus Hotel
3.0 star property
Middletown
5.4 out of 10, (11 reviews)
"There is no front desk. All things considered this is not a $200+ hotel"
United States
Joseph
The price is €196
includes taxes & fees
18 Oct - 19 Oct
Columbus Hotel
A two-story house with a porch, a front door, and a small garden area with potted plants.

2. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (194 reviews)
"Borland House was a pleasant stay. Clean, Friendly, Warm, Historic Feel, Comfortable Bri greeted us when we arrived and was extremely friendly and accommodating Bed was comfortable, room was cozy, very clean, water pressure is sufficient and the building itself gives off a warm and at home vibe. I highly recommend"
United States
Joseph
The price is €119
includes taxes & fees
15 Oct - 16 Oct
Borland House Inn
A large, two-story house with a wrap-around porch and multiple chimneys.

3. Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
3.0 star property
Goshen
10.0 out of 10, Exceptional, (39 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is €254
includes taxes & fees
19 Oct - 20 Oct
Parkway House Goshen Family-Friendly Bed & Breakfast
Exterior

4. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (138 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is €139
includes taxes & fees
21 Oct - 22 Oct
Tin Brook Bed & Breakfast
A dining area with brick flooring, large arched windows, and outdoor seating visible through the windows.

5. Stagecoach Inn

Stagecoach Inn
3.5 star property
Goshen
9.6 out of 10, Exceptional, (79 reviews)
"We only stayed one night, but it was very comfortable and the staff was friendly. "
United States
Kathryn
Stagecoach Inn
A large, white, multi-story house with a symmetrical design, featuring a central entrance and two side wings.

6. Parkway House Goshen Bed & Breakfast Suite #4

Parkway House Goshen Bed & Breakfast Suite #4
Goshen
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Close to everything downtown. Check in was smooth and easy. Would absolutely stay again. "
United States
Michael F.
The price is €411
includes taxes & fees
19 Oct - 20 Oct
Parkway House Goshen Bed & Breakfast Suite #4
A garden with a rock fountain surrounded by various plants and flowers.

7. John H Wallace House

John H Wallace House
4.0 star property
Milford
10.0 out of 10, Exceptional, (20 reviews)
"The house is well located and Eileen was a great host."
United States
Donna
The price is €224
includes taxes & fees
11 Nov - 12 Nov
John H Wallace House
A two-story house with a red front door, a chimney, and a well-maintained lawn.

8. Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
9.8 out of 10, Exceptional, (27 reviews)
"Very nice B&B, with a very gracious host who served us a wonderful breakfast."
United States
Peter
The price is €245
includes taxes & fees
20 Oct - 21 Oct
Villa Verde BB Greenwood Lake NY
A living room with a fireplace, a sectional sofa, and a chandelier.

9. Parkway House Goshen Bed & Breakfast Suite #3

Parkway House Goshen Bed & Breakfast Suite #3
Goshen
10.0 out of 10, Exceptional, (1 review)
"Very comfortable place and Emily is a great host"
United States
James D.
Parkway House Goshen Bed & Breakfast Suite #3
A large, white, two-story house with a wrap-around porch, multiple windows, and two prominent towers.

10. Parkway House Goshen Bed & Breakfast Suite #1

Parkway House Goshen Bed & Breakfast Suite #1
Goshen
The price is €411
includes taxes & fees
20 Oct - 21 Oct
Parkway House Goshen Bed & Breakfast Suite #1
A brick building with a covered patio area featuring outdoor seating and string lights.

11. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (110 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
The price is €364
includes taxes & fees
1 Nov - 2 Nov
Cromwell Manor Inn
A large, two-story house with a wrap-around porch, a chimney, and a car parked in front.

12. Parkway House Goshen Bed & Breakfast Suite #2

Parkway House Goshen Bed & Breakfast Suite #2
Goshen
Parkway House Goshen Bed & Breakfast Suite #2
A bedroom with a wooden dresser, a mirror, a bed with a blue quilt, a window with blinds, and a wall-mounted light switch.

13. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
The price is €339
includes taxes & fees
13 Nov - 14 Nov
Twin Bedroom with Private Bathroom at Storm King Lodge
A large, two-story white house with a wrap-around porch and a small front garden.

14. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (238 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
The price is €109
includes taxes & fees
11 Nov - 12 Nov
The Dominion House Bed & Breakfast
A bedroom with a bed, a window with curtains, a nightstand, and a chair.

15. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
The price is €339
includes taxes & fees
13 Nov - 14 Nov
Loft Room with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

16. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is €407
includes taxes & fees
13 Nov - 14 Nov
Loft Suite with Private Bathroom at Storm King Lodge
A sign for StormKing Lodge with a decorative flower and fox atop it, surrounded by greenery and a paved path.

17. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
The price is €396
includes taxes & fees
13 Nov - 14 Nov
Pine Suite with Private Bathroom at Storm King Lodge
A small, single-story house with a steeply pitched roof, a front porch, and a staircase leading to the entrance.

18. Alpine Haus Bed & Breakfast Inn

Alpine Haus Bed & Breakfast Inn
2.0 star property
Vernon
9.2 out of 10, Wonderful, (344 reviews)
"the beds were very comfortable the breakfast was delicious"
United States
Debbie
The price is €184
includes taxes & fees
22 Oct - 23 Oct
Alpine Haus Bed & Breakfast Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Tru by Hilton Middletown

Tru by Hilton Middletown

8/10 Good
"Hotel was conveniently located to Legoland. The staff were friendly, the rooms were small but clean. Pillows were a little soft. They texted to see if we needed anything and I asked for a couple more pillows and they brought some to the room. There is breakfast included. It wasn’t great but works in a pinch. Good room to have a cheaper stay close to Legoland."
Melissa 2-night trip
Posted 7 hours ago
Tru by Hilton Middletown

Find out more about Middletown

Middletown B&B information

Number of reviews
753
Accommodation
19 B&B
Lowest Price
€109
Highest Price
€481

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.