Pet Friendly Hotels in Chester, MA

There are 3 pet friendly hotels in Chester, and 182 more nearby. All of them welcome two or more pets with no weight limit. Need help to decide where to stay with your dog? 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!

$120

+ Pet fee

Big dogs OK

2+ pets OK

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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$32

+ 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.

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$99+

No pet fee

Big dogs OK

2+ pets OK

Pet-Friendly Airbnb Rentals

Chester, MA

$109

+$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.

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$132

+$75 pet fee

75 lbs 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.

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$133

+$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.

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$126

+$75 pet fee

75 lbs max

2 pets max

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 in designated rooms 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.

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$123

+$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.

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$110

+$45/pet/night

40 lbs max

2 pets max

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield, MA

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG Pet Policy

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG allows 2 dogs up to 40 lbs for an additional fee of $45 per pet, per night. Pets cannot be left unattended in rooms. There is a grassy pet relief area on the property. Sorry, no cats.

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$249

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.

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$60

+$20/pet/night

50 lbs max

2 pets max

Econo Lodge Lee Great Barrington

Lee, MA

Econo Lodge Lee Great Barrington Pet Policy

Econo Lodge Lee Great Barrington welcomes two pets up to 50 lbs in designated rooms for an additional fee of $20 per pet, per night. Both dogs and cats are allowed. Well-behaved pets may be left in the room unattended. There is a grassy area for pet relief on the property.

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$109

+$30/pet/night

60 lbs max

2 pets max

Quality Inn Westfield - Springfield

Westfield, MA

Quality Inn Westfield - Springfield Pet Policy

Quality Inn Westfield - Springfield allows 2 pets up to 60 lbs for an additional fee of $30 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.

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$274

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.

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$247

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.

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$192

+$100 pet fee

Big dogs OK

1 pet max

Sleeps 5

The Mill River Cabin

4.8 Mill River, MA

The Mill River Cabin Pet Policy

This 2-bedroom vacation rental in Mill River allows 1 dog of any size for an additional fee of $100 per stay. Cats may also be allowed by request.

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$143

+$106 per pet

Big dogs OK

2 pets max

Sleeps 4

East Otis Reservoir Cabin With Porch

4.1 Otis, MA

East Otis Reservoir Cabin With Porch Pet Policy

This 2-bedroom vacation rental in Otis allows 2 dogs of any size for an additional fee of $106 per pet, per stay. Sorry, no cats.

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$136

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.

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$246

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.

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$89

+$25/pet/night

Big dogs OK

2 pets max

Pilgrim Inn

Lee, MA

Pilgrim Inn Pet Policy

Pilgrim Inn welcomes two pets of any size for an additional fee of $25 per pet, per night. Both dogs and cats are accepted.

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$137

+$20 pet fee

Big dogs OK

1 pet max

Sleeps 4

Excalibur

4.8 Becket, MA

Excalibur Pet Policy

This 2-bedroom vacation rental in Becket allows 1 dog of any size for an additional fee of $20 per stay. Sorry, no cats.

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There are 3 pet friendly hotels in Chester, MA. All of them welcome two or more pets with no weight limit. Do you know of a pet friendly hotel we've missed? Post a spot to BringFido!