Compare Chesterfield Guest House Rentals

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Featured Guest Houses in Chesterfield

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Feb 15 - Feb 16
Total with taxes and fees
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
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$139 nightly
The price is $150 total per night
$150 total
Jan 29 - Jan 30
Total with taxes and fees
Blooming Inn features free WiFi in public areas, coffee in a common area, and refrigerator in a common area. You can put free offsite parking to good use if you drive.
Free WiFi
Air conditioning
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Jan 29 - Jan 30
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
The Revival House

The Revival House

3 out of 5
17 Commercial St Adams MA
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $168 total per night
$168 total
Jan 29 - Jan 30
Total with taxes and fees
The Revival House features free WiFi in public areas and a communal living room. There's free parking if you drive.
Breakfast included
Parking included
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$131 nightly
The price is $146 total per night
$146 total
Feb 3 - Feb 4
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
Free WiFi
Air conditioning
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
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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.

Hotel Options in Chesterfield

    D. Hotel Suites & Spa

    D. Hotel Suites & Spa

    1 Country Club Rd Holyoke MA
    $124 nightly
    The price is $139 total per night from Jan 29 to Jan 30
    $139 total
    Jan 29 - Jan 30
    Total with taxes and fees
    9.2/10 Wonderful! (2,245 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $121 nightly
    The price is $136 total per night from Feb 26 to Feb 27
    $136 total
    Feb 26 - Feb 27
    Total with taxes and fees
    9/10 Wonderful! (818 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $98 nightly
    The price is $109 total per night from Jan 30 to Jan 31
    $109 total
    Jan 30 - Jan 31
    Total with taxes and fees
    8/10 Very Good! (1,002 reviews)

Chesterfield Guest Houses essential information

Accommodation
6 Guest Houses
Lowest Price
$105
Highest Price
$210
Popular accommodation
The Central Downtown Inn & Suites, Blooming Inn, Berkshire Village Carriage House - Super Private!!, The Revival House, In town, newly remodeled studio with private balcony , Chestnut Lodge