Book Guest Houses in Chester, MA

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Top Guest Houses in Chester

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $173 total per night
$173 total
Jun 9 - Jun 10
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.
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$114 nightly
The price is $127 total per night
$127 total
Jun 11 - Jun 12
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.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$240 nightly
The price is $268 total per night
$268 total
Jun 10 - Jun 11
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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

Granby CT
$219 nightly
The price is $248 total per night
$248 total
Jun 10 - Jun 11
Total with taxes and fees
A garden is available at this guesthouse.
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.
Hill Ross Guest Suite on Historic Homestead

Hill Ross Guest Suite on Historic Homestead

Florence MA
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This guesthouse features a garden, laundry facilities, and barbecue grills.
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

Granby CT
$210 nightly
The price is $239 total per night
$239 total
Jun 30 - Jul 1
Total with taxes and fees
This guesthouse includes a garden and laundry facilities.
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.
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
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This guesthouse features laundry facilities.
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.
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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 Chester

The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
$105 nightly
The price is $117 total per night from Jun 9 to Jun 10
$117 total
Jun 9 - Jun 10
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)

Chester Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$104
Highest Price
$268
Popular accommodation
Hideaway Inn Lenox, The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, The Dewey, Hill Ross Guest Suite on Historic Homestead, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

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