Pet Friendly Hotels in Cheshire, MA

There are 4 pet friendly hotels in Cheshire, and 230 more nearby. 3 welcome two or more pets, and 3 have 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!

$272

+ Pet fee

Big dogs OK

2+ pets OK

Cheshire Airbnb Rentals

Cheshire, MA

Cheshire 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 Cheshire, please contact the host directly or read the House Rules section at the bottom of their listing.

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$163

+ Pet fee

Big dogs OK

2+ pets OK

VRBO Cheshire

Cheshire, MA

VRBO Cheshire 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 Cheshire, 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 Cheshire to collect the pet fee.

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$99+

No pet fee

Big dogs OK

2+ pets OK

Pet-Friendly Airbnb Rentals

Cheshire, MA

$479

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.

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$669

+$100 pet fee

25 kg max

1 pet max

Sleeps 8

Luxury Private Lakefront in the Berkshires

4.9 Cheshire, MA

Luxury Private Lakefront in the Berkshires Pet Policy

This 4-bedroom house in Cheshire allows 1 dog under 50 lbs for an additional fee of $100 per stay. Sorry, no cats or dogs under 2 years old. Pets must be approved in advance.

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$157

+$35 pet fee

Big dogs OK

2 pets max

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield, MA

Best Western Plus Berkshire Hills Inn & Suites Pet Policy

Best Western Plus Berkshire Hills Inn & Suites allows 2 dogs up to 100 lbs of any size in designated rooms for an additional fee of $35 per stay. Pets may be left unattended in rooms. There are walking trails on the property. Sorry, no cats.

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$181

+$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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$254

+$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.

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$169

+$75 pet fee

38 kg 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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$225

+$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.

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$140

+$25/night pet fee

25 kg max

1 pet max

Williamstown Motel

Williamstown, MA

Williamstown Motel Pet Policy

Williamstown Motel welcomes 1 dog up to 50 lbs in designated rooms for an additional fee of $25 plus tax per night. Sorry, no cats.

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$204

+$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.

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$579

+ Pet fee

Big dogs OK

2+ pets OK

Sleeps 14

5-Bedroom House with Indoor and Outdoor Pools

4.6 Lenox, MA

5-Bedroom House with Indoor and Outdoor Pools Pet Policy

This 5-bedroom vacation rental in Lenox is pet friendly! Pets of any size are welcome for no additional fee, however there is a cleaning fee of $150 per stay for all guests. Sorry, no cats.

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$69

+$25/night pet fee

Big dogs OK

2 pets max

Ladd Brook Inn

Pownal, VT

Ladd Brook Inn Pet Policy

Ladd Brook Inn welcomes two pets of any size for an additional fee of $25 per night. Both dogs and cats are allowed, but pets may not be left in the room unattended. There is a pet relief area on the property, and waste bags are available at the front desk.

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$312

+$20/night pet fee

25 kg max

1 pet max

Sleeps 6

Berkshire Lake Access

5.0 Hinsdale, MA

Berkshire Lake Access Pet Policy

This 4-bedroom vacation rental in Hinsdale allows 1 dog under 50 lbs for an additional fee of $20 per night. A second dog may be allowed by request. Sorry, no cats.

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$255

+$25 per pet

Big dogs OK

2+ pets OK

Sleeps 6

Garfield House

4.9 Lee, MA

Garfield House Pet Policy

This 2-bedroom vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

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$426

+$25/pet/night

Big dogs OK

2 pets max

Sleeps 10

Senecal Farms

4.9 Stamford, VT

Senecal Farms Pet Policy

This 4-bedroom vacation rental in Stamford allows 2 dogs of any size for an additional fee of $25 per pet, per night. Sorry, no cats. The property is situated on 100 acres of land.

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$159

+$25 per pet

Big dogs OK

2+ pets OK

Sleeps 4

The Dolly at Garfield House

4.7 Lee, MA

The Dolly at Garfield House Pet Policy

This 1-bedroom vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

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$193

+$45/pet/night

20 kg 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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$363

+$50 pet fee

40 kg max

1 pet max

Berkshire Mountain House

Stephentown, NY

Berkshire Mountain House Pet Policy

Berkshire Mountain House allows 1 dog up to 80 lbs in designated rooms for an additional fee of $50 per stay. There is an off-leash area for dogs on the property. Sorry, no cats.

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There are 4 pet friendly hotels in Cheshire, MA. 3 welcome two or more pets, and 3 have no weight limit. Do you know of a pet friendly hotel we've missed? Post a spot to BringFido!