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

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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
5.0 out of 10, (12 reviews)
"Looks nothing like the pictures shown, a completely different room than what they advertise"
United States
Donald
The price is 2.899.120 ₫
5.182.988 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Columbus Hotel
A large, two-story white house with a wrap-around porch and a small front garden.

2. 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 2.782.638 ₫
3.147.875 ₫ total
includes taxes & fees
9 Nov - 10 Nov
The Dominion House Bed & Breakfast
A two-story house with a porch, a front door, and a small garden area with potted plants.

3. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (195 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 3.348.742 ₫
4.178.098 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Borland House Inn
A large, two-story house with a wrap-around porch and multiple chimneys.

4. 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, (40 reviews)
"One of the best places we’ve stayed at, highly recommended!"
United States
Aakif
The price is 5.239.123 ₫
6.450.669 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Parkway House Goshen Family-Friendly 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
The price is 7.888.454 ₫
9.712.829 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Stagecoach Inn
A garden with a rock fountain surrounded by various plants and flowers.

6. 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 5.943.973 ₫
6.479.016 ₫ total
includes taxes & fees
8 Nov - 9 Nov
John H Wallace House
A two-story house with a red front door, a chimney, and a well-maintained lawn.

7. 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 6.290.055 ₫
7.115.625 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Villa Verde BB Greenwood Lake NY
Exterior

8. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (139 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
The price is 3.559.188 ₫
4.026.671 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Tin Brook Bed & Breakfast
A brick building with a covered patio area featuring outdoor seating and string lights.

9. 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 8.809.105 ₫
10.405.756 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Cromwell Manor Inn
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

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 4.659.300 ₫
5.340.722 ₫ total
includes taxes & fees
19 Oct - 20 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.
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Top Middletown Hotel Reviews

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"Great staff. Onsite restaurant very good. Clean room and lovely grounds."
christina 1-night trip
Posted 15 hours ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Find out more about Middletown

Middletown B&B information

Number of reviews
742
Accommodation
14 B&B
Lowest Price
3.147.875 ₫
Highest Price
10.405.756 ₫

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'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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