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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 Highland

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
Jenny's Country Manor

Jenny's Country Manor

2.0 star property
Red Hook
7.6 out of 10, Good, (133)
"Jenny's was quaint and comfortable, with "
United States
Bill
The price is AED 514
AED 582 total
includes taxes & fees
9 Dec - 10 Dec
Jenny's Country Manor
Aerial view
Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast

4.0 star property
Millbrook
9.0 out of 10, Wonderful, (81)
"Gracious host and great breakfast "
United States
Gerald
The price is AED 727
AED 823 total
includes taxes & fees
4 Jan - 5 January 2026
Millbrook Country House Bed & Breakfast
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
Exterior detail
Inn the Woods Bed and Breakfast

Inn the Woods Bed and Breakfast

3.5 star property
Hyde Park
9.8 out of 10, Exceptional, (136)
"Harry was great, room clean and fresh, breakfast amazing "
United States
Frank
The price is AED 672
AED 760 total
includes taxes & fees
31 Dec - 1 January 2026
Inn the Woods Bed and Breakfast
Terrace/patio
it's a good thing

it's a good thing

4.5 star property
Clinton Corners
8.0 out of 10, Very Good, (24)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
it's a good thing
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 774
AED 1,052 total
includes taxes & fees
18 Dec - 19 Dec
Stonehill's Farmhouse
Design Villa | Egyptian cotton sheets, premium bedding, memory foam beds
Kingston Carriage House

Kingston Carriage House

4.0 star property
Rondout
9.0 out of 10, Wonderful, (27)
"Amazing stay! Just make sure you get a lesson in how to turn the heat on... beautiful property walking distance from sights, shops, and cafes. Will absolutely stay there next time we are in Kingston!"
United States
Andrew
The price is AED 654
AED 761 total
includes taxes & fees
6 Jan - 7 January 2026
Kingston Carriage House
Hiking
Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast

4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (338)
"Great staff, the breakfast was amazing, location to surrounding attractions was great! I would stay again!"
United States
Shawn
The price is AED 823
AED 931 total
includes taxes & fees
9 Dec - 10 Dec
Journey Inn Bed & Breakfast
Property grounds
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Clinton Corners
8.2 out of 10, Very Good, (11)
"The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting."
United States
Dawn B.
The price is AED 514
AED 715 total
includes taxes & fees
9 Dec - 10 Dec
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Property grounds
Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch

Clinton Corners
8.6 out of 10, Excellent, (30)
"It was just as advertised! Host was nice included fruit and coffee "
United States
matt w.
The price is AED 551
AED 760 total
includes taxes & fees
9 Dec - 10 Dec
Private room on secluded 7 acres , access to entire house including patio, porch
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
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3.0 star property
Woodstock
8.4 out of 10, Very Good, (155)
"Beautiful historic home. We had a nice stay. "
United States
Anonymous traveler
The price is AED 694
AED 777 total
includes taxes & fees
9 Dec - 10 Dec
Morning Glory B n B Woodstock NY
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 Highland 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 2 days ago
Holiday Inn Express Poughkeepsie by IHG

Frequently asked questions

Searching for B&Bs in Highland?
If you're looking for something a little quirkier than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. If you're interested in playing some golf on your trip, Apple Greens Golf Course is a good spot to tee off.
Why would you choose B&Bs instead of traditional hotels?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast, B&Bs all have a one-of-a-kind setting.
What are the top B&Bs in Highland?
Here are some well-liked B&Bs in the surrounding area: Stonehill's Farmhouse: 4 rooms. 15.6 mi (25 km) from the downtown core. Enjoy the designer toiletries and sauna. Kingston Carriage House: 5 rooms. 13.6 mi (21.9 km) from the heart of downtown. Enjoy the massage services and private yard. Journey Inn Bed & Breakfast: 7 rooms. Located 5.2 mi (8.4 km) from the core of Highland. Enjoy the free full breakfast and designer toiletries.
When is the best time to stay at a B&B in Highland?
When you're dreaming of a stay in Highland, 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 Highland are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.
What is there to do in Highland?
Spend some time exploring Walkway Over the Hudson State Historic Park and Berean Park Beach if you're hoping to see some of the area's natural features. You might put Franklin D Roosevelt Library & Museum and Franny Reese State Park on your list if you want to see more of the area.
How can I get to and around Highland?
Planning your excursions in and around Highland is easier with these transportation options. Fly into Stewart Intl. Airport (SWF), which is located 16.6 mi (26.7 km) from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.