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Pet Friendly Hotels
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    Pet Friendly Hotels in Chester, MA

    There are 3 pet friendly hotels in Chester, and 181 more nearby. Need help to decide where to stay with your dog? You can browse the results below and filter by amenities to find the perfect spot. BringFido members never pay a booking fee, and their reservations are backed by our Pet Friendly Guarantee!

    Pet Friendly Gedney Farm
    $253
    No pet fee
    Big dogs OK
    1 pet max

    Gedney Farm

    Great Barrington, MA
    Gedney Farm Pet Policy Gedney Farm allows 1 pet of any size for no additional fee. Both dogs and cats are welcome. See Details
    $163
    +$50 pet fee
    Big dogs OK
    2 pets max

    The Black Swan Lee - Lenox an Ascend Collection Hotel

    Lee, MA
    The Black Swan Lee - Lenox an Ascend Collection Hotel Pet Policy The Black Swan Lee - Lenox an Ascend Collection Hotel allows 2 dogs of any size for an additional fee of $50 per stay. Sorry, no cats. See Details
    $99+
    No pet fee
    Big dogs OK
    2+ pets OK

    Pet-Friendly Airbnb Rentals

    Chester, MA
    $190
    +$45 per pet
    Big dogs OK
    2+ pets OK

    Hotel On North

    Pittsfield, MA
    Hotel On North Pet Policy Hotel On North allows pets of any size in designated rooms for an additional fee of $45 per pet, per stay. Both dogs and cats are welcome. See Details
    $203
    +$75 pet fee
    38 kg max
    2 pets max

    Hilton Garden Inn Lenox/Pittsfield

    Pittsfield, MA
    Hilton Garden Inn Lenox/Pittsfield Pet Policy Hilton Garden Inn Lenox/Pittsfield allows 2 pets up to 75 lbs for an additional fee of $75 per stay. Both dogs and cats are welcome, but pets cannot be left unattended. See Details
    $178
    +$85 pet fee
    Big dogs OK
    1 pet max

    Berkshires Untold

    Lenox, MA
    Berkshires Untold Pet Policy Berkshires Untold allows 1 pet of any size in designated rooms for an additional fee of $85 per stay. Both dogs and cats are welcome, but exotic pets are not allowed. Please note that pets cannot be left unattended. See Details
    $277
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 4

    The 1843 Morewood Schoolhouse

    4.9 Pittsfield, MA
    The 1843 Morewood Schoolhouse Pet Policy This 1-bedroom house in Pittsfield is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. There is a fenced yard. Visit Website
    $823
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 8

    Berkshire Lakefront Getaway

    4.9 Monterey, MA
    Berkshire Lakefront Getaway Pet Policy This 5-bedroom house in Monterey is pet friendly! Dogs of any size are allowed for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $192
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Waterfront Summer Cottage

    4.9 Otis, MA
    Waterfront Summer Cottage Pet Policy This 2-bedroom cottage in Otis allows dogs of any size for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $134
    +$25/pet/night
    Big dogs OK
    2 pets max

    Quality Inn Westfield - Springfield

    Westfield, MA
    Quality Inn Westfield - Springfield Pet Policy Quality Inn Westfield - Springfield allows 2 pets of any size for an additional fee of $25 per pet every 2 nights. Both dogs and cats are welcome. There is a grassy pet relief area on the property, as well as a dog park within a quarter of a mile. See Details
    $136
    +$15/pet/night
    25 kg max
    2 pets max

    The Central Downtown Inn & Suites

    Pittsfield, MA
    The Central Downtown Inn & Suites Pet Policy The Central Downtown Inn & Suites welcomes two pets up to 50 lbs in designated rooms for an additional fee of $15 per pet, per night (not to exceed $50 per pet, per week). Both dogs and cats are allowed, and well-behaved pets may be left unattended in rooms. There is a grassy area for pet relief on the property, and waste bags are available at the front desk. Aggressive breeds are not permitted. See Details
    $559
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 8

    William Cook House

    4.9 Middlefield, MA
    William Cook House Pet Policy This 4-bedroom house in Middlefield is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $212
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Waterfront Summer Cottage

    4.9 Otis, MA
    Waterfront Summer Cottage Pet Policy This 2-bedroom cottage in Otis allows dogs of any size for no additional fee. Cats may also be allowed by request. Breed restrictions apply, and all pets must be approved in advance. Visit Website
    $425
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 6

    Berkshire Waterfront Lakehouse

    4.8 Lanesborough, MA
    Berkshire Waterfront Lakehouse Pet Policy This 3-bedroom vacation rental in Lanesborough allows 2 dogs of any size for no additional fee. Pets are not allowed on the furniture. Cats may also be allowed by request. Visit Website
    $535
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 8

    Sophisticated Lenox Retreat Minutes to Downtown

    4.9 Lenox, MA
    Sophisticated Lenox Retreat Minutes to Downtown Pet Policy This 4-bedroom house in Lenox is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $45
    + Pet fee
    Big dogs OK
    2+ pets OK

    Walker Island Camping

    Chester, MA
    Walker Island Camping Pet Policy Dogs are allowed at Walker Island Camping, but they must be kept on a leash when outside your vehicle. Dogs may be walked throughout the park as long as they are cleaned up after. Bags are available for clean up. Dogs are not allowed in the building or pool area and must not be left unattended. Dogs must be kept quiet. For more information on pet restrictions, please call (413) 354-2295. See Details
    $418
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 6

    Shangri-La-Country Retreat

    5.0 Ashfield, MA
    Shangri-La-Country Retreat Pet Policy This 3-bedroom house in Ashfield allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $478
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 9

    Mason Hill

    4.8 Cheshire, MA
    Mason Hill Pet Policy This 3-bedroom barn in Cheshire allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $387
    No pet fee
    Big dogs OK
    1 pet max
    Sleeps 6

    2BR Cabin With Deck & Fire Pit

    4.6 Williamsburg, MA
    2BR Cabin With Deck & Fire Pit Pet Policy This 2-bedroom vacation rental in Williamsburg is pet friendly! Dogs of any size are welcome for no additional fee. Sorry, no cats. Visit Website
    $426
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 10

    Brooksong

    5.0 Dalton, MA
    Brooksong Pet Policy This 5-bedroom house in Dalton allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    Chester, MA, US