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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

Our top choices for Pleasant Valley bed & breakfast

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
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
10 Dec - 11 Dec
Jenny's Country Manor
Dining
Homestead Inn

Homestead Inn

3.5 star property
New Milford
9.2 out of 10, Wonderful, (196)
"Everything was as noted with a friendly staff"
United States
Colby
The price is AED 756
AED 869 total
includes taxes & fees
4 Jan - 5 January 2026
Homestead Inn
Terrace/patio
it's a good thing

it's a good thing

4.5 star property
Clinton Corners
8.2 out of 10, Very Good, (25)
"Wonderful stay and wonderful hosts! "
United States
Daniela-Cristina
it's a good thing
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (301)
"Great stay"
United Kingdom
Katherine
The price is AED 909
AED 1,028 total
includes taxes & fees
10 Dec - 11 Dec
Inn at Pine Plains
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
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 710
AED 828 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
10 Dec - 11 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 711 total
includes taxes & fees
10 Dec - 11 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 756 total
includes taxes & fees
10 Dec - 11 Dec
Private room on secluded 7 acres , access to entire house including patio, porch
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 Pleasant Valley Hotel Reviews

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Buisness friendly, breakfast, gym room, quiet, good customer service "
Luna 1-night trip
Posted 8 hours ago
Courtyard by Marriott Poughkeepsie

Frequently asked questions

Searching for B&Bs in Pleasant Valley?
If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. If your ideal vacation to Pleasant Valley includes spending lots of time outside, Innisfree Garden is a good spot to enjoy the scenery.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to meet other guests, and of course a full breakfast, B&Bs provide a truly one-of-a-kind setting.
What are the best B&Bs in Pleasant Valley?
Here are some B&Bs in the surrounding area: Kingston Carriage House: 5 rooms. 14.6 mi (23.6 km) from the heart of Pleasant Valley. Enjoy the massage services and private yard. Journey Inn Bed & Breakfast: 7 rooms. 6.9 mi (11.2 km) from the downtown core. Enjoy the free full breakfast and designer toiletries. Inn at Pine Plains: 8 rooms. Situated 18.4 mi (29.5 km) from the heart of Pleasant Valley. Jenny's Country Manor: 13 rooms. Located 15.4 mi (24.7 km) from the core of Pleasant Valley.
When is the best time to stay at a B&B in Pleasant Valley?
When you're dreaming of a getaway to Pleasant Valley, year-round temperatures and rainfall may be important factors to consider. 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 32°F. The snowiest months in Pleasant Valley are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.
What is there to do in Pleasant Valley?
When you want to explore some things to do in town, Innisfree Garden and James Baird State Park are some notable sights to visit. You might also consider a trip to sites like Eleanor Roosevelt National Historic Site or Franklin D. Roosevelt Presidential Library and Museum if you have time to see more of the area.
How can I get to and around Pleasant Valley?
Planning your excursions in and around Pleasant Valley is easier with these transportation options. Fly into Stewart Intl. Airport (SWF), which is located 21.7 mi (35 km) from the heart of the city. You can also search for flights into Danbury, CT (DXR-Danbury Municipal), which is 31 mi (49.9 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.