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Cheap Spencertown Hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
$93 nightly
The price is $104 total per night
$104 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
16 mi from city center
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Pool
Pet friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.3 mi from city center
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Pool
Hot Tub
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
$89 nightly
The price is $100 total per night
$100 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.83 mi from city center
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$113 nightly
The price is $126 total per night
$126 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.05 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$191 nightly
The price is $213 total per night
$213 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.19 mi from city center
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
$138 nightly
The price is $154 total per night
$154 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.23 mi from city center
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
$101 nightly
The price is $113 total per night
$113 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
12.67 mi from city center
With a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
$274 nightly
The price is $310 total per night
$310 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
14.74 mi from city center
With a stay at Pocketbook Hotel and Bath in Hudson, you'll be within a 10-minute walk of Hudson Area Library and Stoddard Corner.
Free WiFi
Restaurant
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
$103 nightly
The price is $115 total per night
$115 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.78 mi from city center
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
Pool
Breakfast included
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
$107 nightly
The price is $120 total per night
$120 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
10.68 mi from city center
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute drive from Monument Mountain Reservation.
Pool
Breakfast included
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.14 mi from city center
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
Breakfast included
Pet friendly
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night
$166 total
Dec 12 - Dec 13
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
16.29 mi from city center
Located in Pittsfield, Hotel On North is a 1-minute drive from Barrington Stage Company and 7 minutes from Bousquet Ski Area.
Pet friendly
Parking included
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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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Spencertown hotels essential information

Accommodation
1,349 hotels
Lowest Price
$100
Highest Price
$310
Popular hotels
Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Mountain Lodge, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, The Red Lion Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Pocketbook Hotel and Bath, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Express Hotel & Suites Great Barrington by IHG, Best Western Plus Berkshire Hills Inn & Suites, Hotel On North

Most Recent Spencertown Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5 out of 5
Posted 4 hours ago
CheapTickets Verified Review
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham