Compare Stockbridge Guest House Rentals

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 Guest Houses in Stockbridge

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The price is $122 per night
$122
includes taxes & fees
$109 per night
May 4 - May 5
Guests of The Central Downtown Inn & Suites enjoy free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a terrace and laundry facilities.
Pet friendly
Parking included
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

The price is $333 per night
$333
includes taxes & fees
$330 per night
May 9 - May 10
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Pet friendly
Air conditioning
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
Free WiFi
Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Free WiFi
Parking available
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd, Lee, MA
Guests staying at Jacob's Tanglewood Ranch enjoy free WiFi in public areas, a terrace, and a picnic area. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a fireplace in the lobby.
Pet friendly
Parking included
Vanderbilt Lakeside

Vanderbilt Lakeside

3.5 out of 5
161 Main St, Philmont, NY
Guests of Vanderbilt Lakeside enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. Free parking is available if you drive. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a library, a terrace, and a garden.
Breakfast included
Parking included
1805 House Bed and Breakfast

1805 House Bed and Breakfast

3 out of 5
775 Snydertown Road, Craryville, NY
Guests staying at 1805 House Bed and Breakfast have access to a terrace, a picnic area, and a garden. You can put free parking to good use if you drive. Multilingual staff is on hand to answer questions.
Breakfast included
Parking included
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street, Lee, MA
At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.
Hot Tub
Parking included
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

At this guesthouse, guests have access to features like laundry facilities.
Free WiFi
Air conditioning
Don't see what you're looking for?
See all available properties in Stockbridge
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 Stockbridge

    The Red Lion Inn

    The Red Lion Inn

    30 Main Street, Stockbridge, MA
    The price is $211 per night from May 4 to May 5
    $211
    includes taxes & fees
    $189 per night
    May 4 - May 5
    8.8/10 Excellent! (1,001 reviews)
    Life House Berkshires

    Life House Berkshires

    194 Pittsfield Rd, Lenox, MA
    The price is $115 per night from May 4 to May 5
    $115
    includes taxes & fees
    $103 per night
    May 4 - May 5
    9/10 Wonderful! (573 reviews)
    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

    190 Meadow Street, South Lee, MA
    The price is $134 per night from May 14 to May 15
    $134
    includes taxes & fees
    $120 per night
    May 14 - May 15
    9/10 Wonderful! (625 reviews)

Stockbridge Guest Houses essential information

Accommodation
8 Guest Houses
Lowest Price
$115
Highest Price
$333
Popular accommodation
The Central Downtown Inn & Suites, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Vanderbilt Lakeside, 1805 House Bed and Breakfast , Chestnut Lodge, Cliffwood Cottage by Evergreen Home

Guest Houses in Stockbridge

Most Popular

More Places To Stay in Stockbridge