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Check availability on Pittsfield Romantic Hotels

Top Pittsfield Romantic Hotels

Restaurant
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, (961)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.324.070 ₫
2.595.987 ₫ total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Great stay!"
United States
Ann
The price is 2.608.947 ₫
2.914.115 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is 6.911.605 ₫
7.305.566 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Harbour House Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (799)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is 2.441.222 ₫
2.726.845 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Untold
Outdoor pool, pool loungers
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 3.926.597 ₫
5.563.382 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Red Lion Inn
Front of property – evening/night
The Williams Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (542)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
The price is 5.193.585 ₫
5.801.234 ₫ total
includes taxes & fees
23 Nov - 24 Nov
The Williams Inn
Miscellaneous
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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Top Pittsfield Hotel Reviews

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Frequently asked questions

Searching for romantic hotels in Pittsfield?
Are you in need of a romantic holiday? Our guests also enjoy Pittsfield for its theatre scene and sporting events. If you want to explore the area, you might head to Berkshire Museum, Colonial Theater or Bousquet Ski Area. If you're interested in staying close to a certain attraction, you can sort properties 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 Pittsfield?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Pittsfield: 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 Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Pittsfield?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Pittsfield. Adventurous pairs will enjoy Pittsfield for its sporting events. You might think about visiting Berkshire Museum, Colonial Theater or Bousquet Ski Area.
What's the best way to get to Pittsfield and around town during my romantic getaway?
These transportation options in Pittsfield might help your romantic trip go off without a hitch: The closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 2.5 mi (4 km) from the city centre. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.