Find Romantic Hotels in Chatham, NY from $100

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Top Chatham Romantic Hotels

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1005)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$189 nightly
The price is $212
Dec 18 - Dec 19
Total with taxes and fees
The Red Lion Inn

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (808)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Berkshires Untold

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
$109 nightly
The price is $122
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Nest Hudson

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (268)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$189 nightly
The price is $211
Dec 9 - Dec 10
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
Brook Farm Inn

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown
8.4 out of 10, Very Good, (12)
"Great location and property. thank you"
United States
Christine P.
$244 nightly
The price is $260
Dec 14 - Dec 15
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
$210 nightly
The price is $235
Dec 9 - Dec 10
Total with taxes and fees
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Dec 30 - Dec 31
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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.

Find out more about Chatham

Chatham attractions for couples

In Chatham, New York, families and adventurous travelers alike will find a delightful blend of activities and sights worth exploring. Start your journey at the Chatham Fish & Game Club, where you can participate in various outdoor adventures, from fishing to hiking through scenic trails that showcase the breathtaking beauty of the Hudson Valley. Next, don’t miss the historic Chatham Depot, a charming railway station that adds a touch of nostalgia and offers a glimpse into the region's rich history. For a unique cultural experience, visit the Mac-Haydn Theatre, renowned for its professional summer stock performances that entertain audiences of all ages with musicals and plays. For a more relaxed outing, the Chatham Berry Farm provides a hands-on experience where families can pick their own fruits during the summer, creating memorable moments together. Finally, the nearby Copake Lake offers kayaking and picnicking opportunities, making it a perfect spot for a family day out. When it comes to accommodations, consider staying at one of Chatham's boutique inns or cozy bed-and-breakfasts, where attentive service ensures a pampered experience. Enjoy mornings filled with homemade breakfasts and afternoons spent exploring the picturesque village, all while being just a stone's throw away from these activities.

Top Chatham Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Chatham?
Are you in need of a romantic escape? If you want to explore the area, you might head to The Mac-Haydn Theatre. If you'd like to stay close to a certain attraction, you can sort by neighborhood or distance 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 Chatham?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chatham: 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 Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Chatham?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Chatham. The Mac-Haydn Theatre is one of the local sights that might be worth a stop.
What's the best way to get to Chatham and around town during my romantic getaway?
These transportation options in Chatham might help your romantic trip get off to a smooth start: To get to Chatham, book a flight to Hudson, NY (HCC-Columbia County), which is the closest major airport, located 7.7 mi (12.4 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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