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Pet Friendly Hotels
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    Pet Friendly Hotels in Windsor, MA

    There are 2 pet friendly hotels in Windsor, and 253 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 VRBO Windsor
    $115
    No pet fee
    Big dogs OK
    2+ pets OK

    VRBO Windsor

    Windsor, MA
    VRBO Windsor Pet Policy Pet policies are determined by the individual owner of each Vrbo property. For more information on the pet fee, weight limit and other restrictions at a dog-friendly Vrbo in Windsor, please contact the owner directly or read the 'House Rules' section of their listing. Also be sure to include your pet(s) in the 'Guest' field when making your reservation, so the pet fee can be included. If applicable, it will be usually be displayed in the 'On-site Fees' or 'Owner Fees' sections during checkout. Some owners will also wait until you arrive in Windsor to collect the pet fee. Visit Website
    $67
    No pet fee
    Big dogs OK
    2+ pets OK

    Windsor Airbnb Rentals

    Windsor, MA
    Windsor Airbnb Rentals Pet Policy Pet policies are determined by the individual host of each Airbnb property. For more information on the pet fee, weight limit, and other restrictions at a particular property in Windsor, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $99+
    No pet fee
    Big dogs OK
    2+ pets OK

    Pet-Friendly Airbnb Rentals

    Windsor, MA
    $122
    No pet fee
    Big dogs OK
    2+ pets OK

    The Little Lion

    Great Barrington, MA
    The Little Lion Pet Policy The Little Lion is pet friendly! Dogs of any size are welcome for no additional fee. Cats are also welcome, and well-behaved pets may be left in the room unattended. There are waste bags at the front desk and a grassy pet relief area on the property. See Details
    $150
    +$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
    $146
    +$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
    $196
    +$40 pet fee
    Big dogs OK
    2 pets max

    Shaker Mill Inn

    West Stockbridge, MA
    Shaker Mill Inn Pet Policy Shaker Mill Inn allows 2 pets of any size in designated rooms for an additional fee of $40 per stay. All rooms are pet friendly except the Washington, Greylock, Rockwell, and Family Suite. Both dogs and cats are permitted, and pets may be left unattended if a cell phone number is given to the front desk. The inn provides treats, beds, bowls, mats and a book about dog-friendly places to visit in the area. There are pet waste stations on the property. See Details
    $175
    +$40/pet/night
    Big dogs OK
    2 pets max

    Hotel Downstreet an Ascend Collection Hotel

    North Adams, MA
    Hotel Downstreet an Ascend Collection Hotel Pet Policy Hotel Downstreet an Ascend Collection Hotel allows 2 pets of any size for an additional fee of $40 per pet, per night. Both dogs and cats are welcome, but pets must be crated if left unattended in rooms. See Details
    $171
    +$25/pet/night
    Big dogs OK
    2 pets max

    Berkshire Valley Inn

    Williamstown, MA
    Berkshire Valley Inn Pet Policy Berkshire Valley Inn welcomes two pets of any size in designated rooms for an additional fee of $25 per pet, per night. Both dogs and cats are welcome. See Details
    $106
    +$25/pet/night
    Big dogs OK
    2 pets max

    Willows Motel Williamstown

    Williamstown, MA
    Willows Motel Williamstown Pet Policy Willows Motel Williamstown welcomes two pets of any size for an additional fee of $25 per pet, per night. There are only four pet-friendly rooms. Guests with pets must call (877) 411-3436 prior to booking to verify availability of a pet-friendly room or risk not being able to check in with a pet and/or incurring any associated cancellation penalties. Both dogs and cats are allowed, but pets may not be left unattended in the rooms. There are grassy areas for pet relief on the property. See Details
    $200
    +$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
    $162
    +$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
    $244
    No pet fee
    Big dogs OK
    2 pets max

    Clover Hill Farm

    Williamstown, MA
    Clover Hill Farm Pet Policy Clover Hill Farm welcomes 2 dogs of any size in designated rooms for no additional fee. Pets may be left unattended in rooms. There are 100 acres of land on the property for dog walking. Cats are considered with prior approval. See Details
    $557
    No pet fee
    Big dogs OK
    2+ pets OK

    Chesapeake Inn of Lenox

    Lenox, MA
    Chesapeake Inn of Lenox Pet Policy Chesapeake Inn of Lenox is pet friendly! Pets of any size are welcome for no additional fee. Pets are only allowed in Barn Rooms, not the main house. Both dogs and cats are permitted, but pets may not be left unattended. There is a grassy relief area right outside the barn entrance. See Details
    $270
    +$25 pet fee
    Big dogs OK
    2 pets max

    Whistler's Inn Bed & Breakfast

    Lenox, MA
    Whistler's Inn Bed & Breakfast Pet Policy Whistler's Inn Bed & Breakfast allows 2 dogs of any size in designated rooms for an additional fee of $25 per pet, per night for dogs up to 25 lbs and $35 per pet, per night for larger dogs Sorry, no cats. Pets are not permitted on the furniture or in the dining room at breakfast time. Please clean up after your pets. See Details
    $379
    No pet fee
    Big dogs OK
    2+ pets OK

    The Cottage

    Stockbridge, MA
    The Cottage Pet Policy The Cottage is pet friendly! Dogs of any size are welcome in designated rooms for no additional fee. Cats may also be allowed by request. See Details
    $265
    +$75/pet/night
    Big dogs OK
    2 pets max

    The Red Lion Inn

    Stockbridge, MA
    The Red Lion Inn Pet Policy The Red Lion Inn allows 2 pets of any size in designated rooms for an additional fee of $75 per pet, per night. Only ground-floor rooms are pet friendly. Guests with pets must call (877) 411-3436 prior to booking to verify availability of a pet-friendly room or risk not being able to check in with a pet and/or incurring any associated cancellation penalties. Both dogs and cats are welcome, but pets must be crated if left unattended. Pets receive treats, bowls, and use of a crate at check-in. Guests can walk their dogs at the park down the street from the hotel. Three pets are considered with prior approval. See Details
    $152
    +$30 per pet
    Big dogs OK
    2+ pets OK

    Maple Terrace Motel

    Williamstown, MA
    Maple Terrace Motel Pet Policy Maple Terrace Motel welcomes dogs of any size in designated rooms for an additional fee of $30 per pet, per stay. Deluxe Rooms and Suites are not pet friendly. Dogs may not be left unattended in the room. Treats and waste bags are provided, and there is a grassy area on the property for pet relief. Sorry, cats are not allowed. See Details
    $802
    No pet fee
    Big dogs OK
    1 pet max

    Inn at Kenmore Hall

    Richmond, MA
    Inn at Kenmore Hall Pet Policy Inn at Kenmore Hall allows dogs of any size with a pet deposit of $100. Food and water bowls are provided in the room. Sorry, no cats. See Details
    $241
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Suite at East Berkshire Chalet

    4.7 Charlemont, MA
    Suite at East Berkshire Chalet Pet Policy This 2-bedroom apartment in Charlemont is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    Windsor, MA, US