Hotels in Pine Plains

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This weekend
May 22 - May 24
Next weekend
May 29 - May 31

Where to stay in Pine Plains?

Free daily continental breakfast

Inn at Pine Plains

Inn at Pine Plains
3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (306 reviews)
Wake up to a continental breakfast at this charming Pine Plains B&B, just minutes from the local library and The Stissing Center. Visitors praise the attentive staff, while free parking and daily housekeeping ensure a hassle-free Hudson Valley escape.
The price is $275
$311 total
includes taxes & fees
May 19 - May 20
Inn at Pine Plains
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (179 reviews)
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
The price is $156
$179 total
includes taxes & fees
May 19 - May 20
Blackberry River Inn
Exterior

Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is $1,130
$1,700 total
includes taxes & fees
May 19 - May 20
Las Flores Villa
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
The price is $105
$121 total
includes taxes & fees
May 19 - May 20
Locust Tree Bed and Breakfast LLC
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (85 reviews)
This countryside motel offers free WiFi and parking with 24-hour front desk assistance. Located near Housatonic Meadows State Park and Clarke Outdoors, it's perfect for outdoor enthusiasts looking to explore hiking trails and snowboarding venues.
The price is $130
$150 total
includes taxes & fees
May 19 - May 20
Hitching Post Country Motel
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (161 reviews)
This charming Cornwall Bridge lodge offers free WiFi, parking, and daily continental breakfast. Swim in the seasonal outdoor pool or unwind on the terrace surrounded by gardens. Kent Falls State Park and the Appalachian Trail provide nearby adventure opportunities.
The price is $212
$243 total
includes taxes & fees
May 19 - May 20
Cornwall Inn and Lodge
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (48 reviews)
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
The price is $173
$193 total
includes taxes & fees
May 20 - May 21
Wilder House Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (44 reviews)
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
The price is $147
$164 total
includes taxes & fees
Jun 1 - Jun 2
East Rock Inn
Lobby sitting area

The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn
2.0 star property
Kent
10.0 out of 10, Exceptional, (4 reviews)
This intimate inn offers free WiFi and parking just minutes from Morrison Gallery and Eric Sloane Museum. Enhance your stay with in-room massages after exploring nearby attractions or venture to the Appalachian Trail, just 24 minutes away.
The price is $297
$342 total
includes taxes & fees
May 19 - May 20
The Kent Collection - The Firefly Inn
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (780 reviews)
This tranquil hotel offers sound-insulated accommodations near Housatonic River and River Walk. Guests love the helpful staff, clean rooms, indoor pool, and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while exploring Great Barrington's nearby restaurants.
The price is $195
$217 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (765 reviews)
Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.
The price is $124
$139 total
includes taxes & fees
May 25 - May 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (855 reviews)
The price is $76
$85 total
includes taxes & fees
May 19 - May 20
Monument Mountain Motel
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
The price is $190
$212 total
includes taxes & fees
May 19 - May 20
The Berkshire Mountain Inn
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,009 reviews)
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
The price is $85
$94 total
includes taxes & fees
May 25 - May 26
Quality Inn Great Barrington
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (12 reviews)
This 4-star Salisbury guesthouse offers free WiFi and parking while being close to Mount Frissell. Outdoor enthusiasts will appreciate nearby snowboarding and canoeing options. Relax in the garden after exploring Scoville Memorial Library.
The price is $594
$683 total
includes taxes & fees
May 19 - May 20
9 Academy
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (151 reviews)
A charming stay in Salisbury at this historic hotel with a welcoming bar and café. Unwind in the peaceful garden or relax on the terrace after exploring nearby Mount Frissell and Hanging Rock Park. Free breakfast, WiFi, and parking enhance your visit.
The price is $343
$395 total
includes taxes & fees
May 19 - May 20
The White Hart
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (297 reviews)
Nestled beside a golf course in Lakeville, this resort offers a seasonal outdoor pool and rejuvenating deep-tissue massages at the spa. Unwind at the bar after dining at the on-site restaurant, or maintain your routine in the fitness center, all while enjoying free WiFi and parking.
The price is $259
$298 total
includes taxes & fees
May 19 - May 20
Interlaken Inn & Resort
Exterior

Troutbeck

Troutbeck
5.0 star property
Amenia
Escape to a luxurious retreat in Amenia where rejuvenating spa treatments await. Minutes from Amenia Free Library and Sharon Playhouse, this tranquil hotel features an outdoor pool, restaurant and bar. Free WiFi and parking complement your countryside getaway.
The price is $572
$687 total
includes taxes & fees
May 20 - May 21
Troutbeck
Interior

Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
3.0 star property
Great Barrington
The price is $920
$1,528 total
includes taxes & fees
May 28 - May 29
Charming 6 Bdrm Countryside Stay
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (26 reviews)
Relish free breakfast before exploring the Harlem Valley Rail Trail and Yoakum Preserve. This hotel offers complimentary WiFi and parking, with the on-site restaurant serving Mediterranean dishes for lunch and dinner in charming surroundings.
The price is $251
$284 total
includes taxes & fees
May 19 - May 20
The Millerton 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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When is the best time to visit Pine Plains?

Our prices for hotels in Pine Plains are cheapest in September
Price trends for hotels in Pine Plains
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Pine Plains
May
High 19°C / low 9°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 24 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 15 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 2 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature -1 degrees Celsius, average low temperature -8 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 6 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
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Monthly weather averages (˚C)

Top landmarks in Pine Plains

Stissing Lake Park

Stissing Lake Park is 0.8 mi (1.3 km) from central Pine Plains, why not stop by during your stay. If you like Stissing Lake Park, you'll love Northern Dutchess Botanical Gardens and Stanford Recreation Park, both just a short drive away.
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Learn more about Pine Plains

Pine Plains is well-known for its attractions such as Stissing Lake Park and The Stissing Center.

See all hotels in Pine Plains
Sharon Ct, USA Fall foliage and autumn colors.

Check out reviews of Pine Plains hotels guests love

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"The pool was closed so my husband didn’t get to go in"
Lauren 1-night trip
Posted 4 hours ago
Best Western Plus Kingston Hotel And Conference Center

Frequently asked questions

What hotels do travelers recommend in Pine Plains?
Guests like Inn at Pine Plains.
Can I book a refundable hotel in Pine Plains?
If you want the flexibility to change your travel plans to Pine Plains, most accommodations offer refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Pine Plains if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 25 vacation homes.
What will the weather in Pine Plains be like during my visit?
The warmest months in Pine Plains are usually July and August with an average temp of 67°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.
Why should I book my Pine Plains hotel with Hotels.com?
There are plenty of reasons to book your Pine Plains travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.