Find Romantic Hotels in Pine Plains, NY

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Check availability on Pine Plains Romantic Hotels

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Pine Plains romantic hotels

Front of property
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn
3.5 star property
Rhinebeck Village
8.4 out of 10, Very Good, (810)
"I’ve stayed at the Beckman Arms many times, in all of the various parts (motel, Delamater House, etc) and have never been disappointed. The location is exceptional, the rooms are cozy and clean, and parking is great. I highly recommend it if you’re staying in the area."
United States
Armand
The price is ₩153,148
₩173,248 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Beekman Arms and Delamater Inn
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (273)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is ₩258,626
₩297,420 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Interlaken Inn & Resort
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ₩237,326
₩272,925 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Blackberry River Inn
Shared fridge, microwave
The Nest Hudson

The Nest Hudson

The Nest Hudson
3.5 star property
Hudson
9.6 out of 10, Exceptional, (211)
"The suite was perfect, charming, roomy. Parking is on the street, which was a concern, but we had no problem. Very walkable to shopping and restaurants. Lovely stay."
United States
Beth
The Nest Hudson
Exterior
Mirbeau Inn & Spa

Mirbeau Inn & Spa

Mirbeau Inn & Spa
4.0 star property
Rhinebeck Village
9.6 out of 10, Exceptional, (309)
"The inn was lovely with attentive staff!"
United States
Karen
The price is ₩619,489
₩753,885 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Mirbeau Inn & Spa
Restaurant
Hotel Kinsley

Hotel Kinsley

Hotel Kinsley
3.5 star property
Stockade District
9.0 out of 10, Wonderful, (332)
"Room was great and staff very friendly"
Canada
Byron
The price is ₩317,903
₩413,812 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Hotel Kinsley
Exterior
The Millerton Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (9)
"Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!"
United States
Jason
The price is ₩238,511
₩269,815 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Millerton Inn
View from room
Diamond Mills Resort

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
Saugerties
9.4 out of 10, Exceptional, (346)
"Amazing view from the room. We had a great stay. "
United States
Adam
The price is ₩354,726
₩433,411 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Diamond Mills Resort
Front of property
it's a good thing

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
8.2 out of 10, Very Good, (25)
"Lynn was a wonderful & accommodating host. Tje"
United States
Julie-Anne
it's a good thing
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 Pine Plains Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Pine Plains?
If you and your partner need a romantic escape, we'd like to help you plan for it. You might consider checking out some of the nearby sights and attractions such as The Stissing Center, Stissing Lake Park, or Thompson Pond. If you're interested in staying close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Pine Plains?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Pine Plains: The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Pine Plains are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.
What is there to do in Pine Plains?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all there is to see and do in Pine Plains. A visit to The Stissing Center, Stissing Lake Park, or Thompson Pond might be just the ticket when you're checking out the sights.
What's the best way to get to Pine Plains and around town during my romantic getaway?
These transportation options in Pine Plains might help your romantic trip get off to a smooth start: Make your way to Pine Plains with a flight to Hudson, NY (HCC-Columbia County), which is the closest major airport located 21.9 mi (35.3 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.