Pet Friendly Hotels in Chester, MA

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.

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$166

+$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.

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.

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.

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.

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.

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.

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.

Hampton Inn & Suites Berkshires Lenox

Lenox, MA

Hampton Inn & Suites Berkshires Lenox Pet Policy

Hampton Inn & Suites Berkshires Lenox welcomes two pets with a combined weight up to 75 lbs for an additional fee of $75 for stays of 1 to 4 nights and $125 for longer stays. Both dogs and cats are allowed. Pets may be left unattended in rooms for up to three hours if crated. Beds and bowls are available, and there are two pet relief areas on the property.

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.

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.

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.

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.

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.

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.

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.

VRBO Chester

Chester, MA

VRBO Chester 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 Chester, 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 Chester to collect the pet fee.

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