Book Guest Houses in Great Barrington, MA

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Top Guest Houses in Great Barrington

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night
$111 total
Oct 15 - Oct 16
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $164 total per night
$164 total
Nov 10 - Nov 11
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Oct 19 - Oct 20
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
9 Academy

9 Academy

4 out of 5
9 Academy St Salisbury CT
$594 nightly
The price is $683 total per night
$683 total
Oct 14 - Oct 15
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-in, and express check-out are also on offer.
Parking included
Free WiFi
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Granby CT
$239 nightly
The price is $271 total per night
$271 total
Nov 2 - Nov 3
Total with taxes and fees
A garden is available at this guesthouse.
Air conditioning
Parking available
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
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A garden is available at this guesthouse.
Pet friendly
Free WiFi
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

Great Barrington MA
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This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
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This guesthouse features laundry facilities.
Free WiFi
Air conditioning
1805 House Bed and Breakfast

1805 House Bed and Breakfast

3 out of 5
775 Snydertown Road Craryville NY
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This guesthouse features free self parking and a terrace. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Parking included
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
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A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
Hot Tub
Parking included
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
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.

Top hotels in Great Barrington

Prospect Berkshires

Prospect Berkshires

50 Prospect Lake Rd Egremont MA
$345 nightly
The price is $385 total per night from Nov 10 to Nov 11
$385 total
Nov 10 - Nov 11
Total with taxes and fees
10/10 Exceptional! (45 reviews)

Great Barrington Guest Houses essential information

Accommodation
13 Guest Houses
Lowest Price
$74
Highest Price
$683
Popular accommodation
The Central Downtown Inn & Suites, Hideaway Inn Lenox, Berkshire Village Carriage House - Super Private!!, 9 Academy , A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, The Dewey, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, 1805 House Bed and Breakfast , Chestnut Lodge, Jacob's Tanglewood Ranch

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