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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

B&B in Montgomery

Exterior detail
Borland House Inn

Borland House Inn

3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
Exterior
Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY

4.0 star property
Monroe
10.0 out of 10, Exceptional, (13)
"Amazing breakfast, scenery, tucked away on a hilltop, what a getaway! "
United States
Gary
The price is AED 622
AED 777 total
includes taxes & fees
11 Dec - 12 Dec
Villa Verde BB Greenwood Lake NY
Breakfast, lunch and dinner served
Stonehill's Farmhouse

Stonehill's Farmhouse

3.5 star property
Accord
9.6 out of 10, Exceptional, (48)
"Very cute, clean, friendly and well priced country motel! "
United States
Katya
The price is AED 782
AED 1,061 total
includes taxes & fees
18 Dec - 19 Dec
Stonehill's Farmhouse
Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is AED 790
AED 893 total
includes taxes & fees
10 Dec - 11 Dec
The Dominion House Bed & Breakfast
Restaurant
Stagecoach Inn

Stagecoach Inn

3.5 star property
Goshen
9.6 out of 10, Exceptional, (78)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
United States
Theresa
The price is AED 863
AED 1,063 total
includes taxes & fees
4 Jan - 5 January 2026
Stagecoach Inn
Exterior
Cromwell Manor Inn

Cromwell Manor Inn

4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
Cromwell Manor 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 Montgomery Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"The was extremely clean"
Dewayne 1-night trip
Posted 1 day ago
Holiday Inn Express Poughkeepsie by IHG

Frequently asked questions

Searching for B&Bs in Montgomery?
If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your vacation. While you're here, you can get to know Montgomery by exploring its natural beauty. Consider a stop by Orange County Arboretum and Thomas Bull Memorial Park.
Are you thinking about a B&B instead of a traditional hotel?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast, B&Bs all have a truly one-of-a-kind environment.
What are the top B&Bs in Montgomery?
Check out these B&Bs in Montgomery: Borland House Inn: 5 rooms. Enjoy the free full breakfast and deli. Buck's Homestead B&B: 3 rooms. Secluded Ranch Retreat with Pool, Hot Tub,Sauna: Enjoy the in-room fireplace and hot tub.
When should I book my B&B in Montgomery?
When you're dreaming of a trip to Montgomery, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Montgomery?
When you want to spend some time in the great outdoors, Orange County Arboretum and Thomas Bull Memorial Park are some notable spots. You might put City Winery Hudson Valley and Highland Lakes State Park on your list if you want to see more of the area.
How can I get to and around Montgomery?
Mapping out your trip in and around Montgomery is easy with these transportation options. Fly into Stewart Intl. Airport (SWF), which is located 8 mi (12.9 km) away from the heart of the city. If you'd like to venture out around the area, you may want to rent a car for your trip.