Find Romantic Hotels in Pine Plains, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pine Plains Romantic Hotels

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
8.4 out of 10, Very Good, (807)
"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 ₩151,995
₩171,944 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, (271)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is ₩263,017
₩302,469 total
includes taxes & fees
Dec 18 - Dec 19
Interlaken Inn & Resort
Shared fridge, microwave
The Nest Hudson

The Nest Hudson

The Nest Hudson
3.5 star property
Hudson
9.6 out of 10, Exceptional, (210)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson
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 ₩241,356
₩277,560 total
includes taxes & fees
Dec 18 - Dec 19
Blackberry River Inn
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 ₩236,715
₩267,783 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Millerton Inn
Restaurant
Hotel Kinsley

Hotel Kinsley

Hotel Kinsley
3.5 star property
Stockade District
9.0 out of 10, Wonderful, (330)
"Room was great and staff very friendly"
Canada
Byron
The price is ₩323,301
₩420,839 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Hotel Kinsley
Exterior
Mirbeau Inn & Spa

Mirbeau Inn & Spa

Mirbeau Inn & Spa
4.0 star property
Rhinebeck
9.6 out of 10, Exceptional, (308)
"The inn was lovely with attentive staff!"
United States
Karen
The price is ₩630,008
₩766,686 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Mirbeau Inn & Spa
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 ₩360,749
₩440,771 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Diamond Mills Resort
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.
View all properties

Top Pine Plains Hotel Reviews

Explore a world of travel with Expedia

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.