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Check availability on Hinsdale Romantic Hotels

Our top choices for Hinsdale romantic hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay there!! Very friendly staff"
United States
Ann
The price is 1.971.504 ₫
2.202.171 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
The price is 3.927.193 ₫
4.151.043 ₫ total
includes taxes & fees
13 Dec - 14 Dec
UU Rowe Camp and Conference Center
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.443.294 ₫
2.729.160 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.927.193 ₫
5.564.226 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
The Red Lion Inn
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (813)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is 2.889.966 ₫
3.228.091 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Berkshires Untold
Front of property – evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (549)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is 5.194.965 ₫
5.802.776 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Williams Inn
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is 5.666.755 ₫
5.989.892 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn
Miscellaneous
1896 House Country Inn & Motels

1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (448)
"The price is good. It's a classic motel from the '50's, but gets the job done."
United States
edson
1896 House Country Inn & Motels
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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Frequently asked questions

Searching for romantic hotels in Hinsdale?
Are you in need of a romantic getaway? If you want to explore the area, you might head to Bas Ridge Golf Course. If you'd like to stay close to a certain attraction, you can sort by neighbourhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Hinsdale?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Hinsdale: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Hinsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Hinsdale?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all there is to see and do in Hinsdale. Bas Ridge Golf Course is one of the local sights that might be worth a stop.
What's the best way to get to Hinsdale and around town during my romantic getaway?
These transportation options in Hinsdale might help your romantic trip get off to a smooth start: If you're looking to fly to Hinsdale, the closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.7 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.