Search Romantic Hotels in Pittsfield

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Check availability on Pittsfield Romantic Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Pittsfield Romantic Hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (743)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is 2.307.873 ₫
2.577.895 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (889)
"Excellent customer service and great rooms"
The price is 2.716.728 ₫
3.034.585 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Nice area to visit "
The price is 3.537.022 ₫
3.950.861 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (512)
"Great hotel, staff and restaurant!"
The price is 5.582.480 ₫
6.235.630 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Williams Inn
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"great place have stayed several times, and hope to return."
The price is 4.457.544 ₫
6.157.556 ₫ total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"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!! "
The price is 6.918.425 ₫
7.312.775 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Harbour House Inn
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (548)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is 2.702.459 ₫
3.018.647 ₫ total
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (325)
"Great spot. Lots of history. "
The price is 4.800.432 ₫
5.361.977 ₫ total
includes taxes & fees
29 Oct - 30 Oct
The Dewey
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 Barrington Stage Company. 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 Barrington Stage Company.
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.