Compare Inns in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Inns in Pittsfield

Gregory House Country Inn

Gregory House Country Inn

3 out of 5
3016 New York 43 Averill Park NY
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $125 total per night
$125 total
Dec 5 - Dec 6
Total with taxes and fees
Guests staying at Gregory House Country Inn enjoy free WiFi in public areas, a terrace, and a fireplace in the lobby. Free parking is included with your stay. This inn also has a picnic area.
Parking included
Free WiFi
Apple Tree Inn

Apple Tree Inn

3 out of 5
10 Richmond Mountain Rd Lenox MA
Guests of Apple Tree Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and express check-out. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include a terrace, a garden, and a picnic area.
Pool
Breakfast included
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 out of 5
910 Cold Spring Road Williamstown MA
$113 nightly
The price is $127 total per night
$127 total
Dec 9 - Dec 10
Total with taxes and fees
1896 House Country Inn & Motels features free WiFi in public areas, conference space, and a business center. Free parking is included with your stay. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include a computer station, a terrace, and wedding services.
Pet friendly
Parking included
The Egremont Village Inn

The Egremont Village Inn

3 out of 5
17 Main Streeet South Egremont MA
At The Egremont Village Inn, guests enjoy features like a nightclub, karaoke, and free WiFi in public areas. There's free parking and an airport shuttle for a fee. Staff members are on hand to provide dry cleaning/laundry services, tour or ticket assistance, and luggage storage. Additional amenities include a meeting room, an arcade/game room, and a library.
Pet friendly
Parking included
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
Guests of Kemble Inn enjoy free WiFi in public areas, a hot tub, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with luggage storage and tours/tickets. Other amenities at this boutique inn include coffee/tea in a common area, a library, and free newspapers.
Hot Tub
Breakfast included
The Kemble Berkshires

The Kemble Berkshires

2 out of 5
2 Kemble St Lenox MA
Guests staying at The Kemble Berkshires enjoy free WiFi in public areas, a terrace, and barbecue grills. If you decide to drive, there's free parking. This inn also has a garden.
Parking included
Free WiFi
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

Hotel Options in Pittsfield

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $101 nightly
    The price is $113 total per night from Jan 4 to Jan 5
    $113 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (776 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $93 nightly
    The price is $104 total per night from Dec 5 to Dec 6
    $104 total
    Dec 5 - Dec 6
    Total with taxes and fees
    7.8/10 Good! (975 reviews)
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St Pittsfield MA
    $93 nightly
    The price is $104 total per night from Dec 7 to Dec 8
    $104 total
    Dec 7 - Dec 8
    Total with taxes and fees
    8.4/10 Very Good! (1,004 reviews)

Inns

Find a great Pittsfield inn
If you’re on the lookout for a place to stay in Pittsfield that sports special touches and décor but is less costly than a bed and breakfast, rent a room at an inn. Whether you’re staying for a day, a week or a month, Orbitz has a great selection of super-comfy Pittsfield inns to choose from.

Pick the right inn for you
The most popular hotel inns in Pittsfield merge the convenience of an inn with many of the standard features of a hotel. Think pools and gyms, without the hefty price tag.

You’ll find Pittsfield inns are located in all sort of convenient neighborhoods, making them a great option for those traveling on four wheels. They can also offer a tasty breakfast and hearty dinner, saving you the time and effort it would take to find good eats in a new place. 

If you want a space filled with loads of personality and a good helping of hospitality to boot, look out for historic inns. Privately owned with an exclusive number of rooms, you’ll receive a more personalized stay, much like a boutique hotel. No matter what type of inn you choose, you’re sure to enjoy unique experiences you won’t find anywhere else.

Pittsfield Inns essential information

Accommodation
6 Inns
Lowest Price
$104
Highest Price
$127
Popular accommodation
Gregory House Country Inn, Apple Tree Inn, 1896 House Country Inn & Motels, The Egremont Village Inn, Kemble Inn, The Kemble Berkshires

More to Explore