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Search Guest Houses in Stockbridge

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Our top choices for Stockbridge guest houses

Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
$94 nightly
The price is $105
Dec 28 - Dec 29
Total with taxes and fees
The Central Downtown Inn & Suites
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (271)
"We enjoyed our stay. Excellent location to explore Western Mass!"
United States
Charles D.
$187 nightly
The price is $209
Dec 24 - Dec 25
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
Exterior
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage
Hillsdale
10.0 out of 10, Exceptional, (17)
"Wonderful place - great location. Beautiful cottage and perfectly designed. Had everything we needed for a lone weekend."
United States
Lauren P.
$305 nightly
The price is $310
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hudson valley and The Berkshires Cottage
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 Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Stockbridge

Stockbridge Guest Houses information

Number of reviews
632
Accommodation
10 Guest Houses
Lowest Price
$105
Highest Price
$310

Frequently asked questions

What is the nightly rate for a guest house in Stockbridge?
Rates for Stockbridge guest houses vary, but travelers can find great-value prices from $105 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Stockbridge guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Stockbridge guest house and a B&B?
A guest house in Stockbridge is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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