Most Romantic Hotels in Pittsfield

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Check availability on Pittsfield Romantic Hotels

Top Pittsfield Romantic Hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (687)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is RM673
RM752 total
includes taxes & fees
24 Aug - 25 Aug
Berkshires Untold
The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (486)
"The property was spacious but still had a cozy feel. "
The price is RM982
RM1,097 total
includes taxes & fees
7 Sept - 8 Sept
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, (1006)
"Loved our visit"
The price is RM796
RM1,077 total
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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 RM1,105
RM1,168 total
includes taxes & fees
25 Aug - 26 Aug
Harbour House Inn
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (521)
"Great place , love it, will return"
The price is RM629
RM702 total
includes taxes & fees
15 Sept - 16 Sept
The Constance by the Lenox Collection
1896 House Country Inn & Motels
Miscellaneous

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (434)
"Near hiking for Mt. Greylock and the Appalachian Trail. Nice walking area close by at Lamb's Hill. Clean Older mattress, was OK, but could feel springs a little. If you like a tub, it is tiny. The shower is OK"
1896 House Country Inn & Motels
Brook Farm Inn
1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (157)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
Brook Farm Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
The price is RM730
RM816 total
includes taxes & fees
19 Aug - 20 Aug
Whistler's Inn Bed & Breakfast
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.

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Very clean, fantastic staff, comfortable bed, robes to use gping to the pool/jacuzzi, plus the large bottles of water in the room. "
Victoria 1-night trip
Posted 4 days ago
The Red Lion Inn

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.
What's the best place to stay for a romantic holiday to Pittsfield?
Hotel On North is a favourite hotel for couples, and features premium bedding and flat-screen TVs.
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.