Pet Friendly Holiday Rentals

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Pet Friendly Holiday Rentals

Pet Friendly Holiday Rentals in Chester, CT

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There are 4 pet friendly holiday rentals in Chester, and 221 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. All pet policy information is guaranteed and there are no booking fees!

Pet Friendly Duckling Crossing

Big Dogs Allowed

2+ Pets Allowed

Duckling Crossing

5.0 Westbrook, CT

Duckling Crossing Pet Policy

Dogs of any size are allowed at this 4-bedroom house in Westbrook for an additional fee of $25 per pet, per night. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Brodeur Family Cottage - 64 S

4.5 Old Lyme, CT

Brodeur Family Cottage - 64 S Pet Policy

This 2-bedroom vacation rental in Old Lyme allows dogs of any size for an additional fee of $10 per pet, per night. Sorry, no cats.

Big Dogs Allowed

2+ Pets Allowed

North Fork Waterfront Gem

4.7 East Marion, NY

North Fork Waterfront Gem Pet Policy

This 2-bedroom vacation rental in East Marion allows 4 dogs of any size for an additional fee of $20 per pet, per night. Sorry, no cats. All pets must be approved in advance.

Big Dogs Allowed

Beautiful Crescent Beach House

5.0 Niantic, CT

Beautiful Crescent Beach House Pet Policy

This 4-bedroom vacation rental in Niantic allows 1 dog of any size for no additional fee. All pets must be approved in advance. Sorry, no cats.

Small Dogs Only

2+ Pets Allowed

Villa with Fireplace & Garden

4.8 Colchester, CT

Villa with Fireplace & Garden Pet Policy

This 2-bedroom villa in Colchester allows 2 dogs under 20 lbs for no additional fee. Cats are also welcome.

Big Dogs Allowed

2+ Pets Allowed

Exclusive North Cove

4.7 Old Saybrook, CT

Exclusive North Cove Pet Policy

This 3-bedroom vacation rental in Old Saybrook allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Spacious House with Pool Near Beaches

5.0 Waterford, CT

Spacious House with Pool Near Beaches Pet Policy

This 3-bedroom house in Waterford allows 2 dogs of any size for an additional fee of $30 per pet, per night. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Beachfront Dream House in Long Island Sound

Beachfront Dream House in Long Island Sound Pet Policy

Dogs of any size are allowed at this 4-bedroom house in Orient for an additional fee of $50 per pet, per night. Cats may also be allowed by request.

Small Dogs Only

Old Lyme Shores Beach House

5.0 Old Lyme, CT

Old Lyme Shores Beach House Pet Policy

This 4-bedroom estate in Old Lyme allows 1 dog under 20 lbs for no additional fee. Cats may also be allowed by request.

Small Dogs Only

Maison de La Mer

5.0 East Marion, NY

Maison de La Mer Pet Policy

This 3-bedroom house in East Marion allows 1 dog under 20 lbs for no additional fee. Cats are also welcome.

Small Dogs Only

Charming Northfork Getaway

5.0 Greenport, NY

Charming Northfork Getaway Pet Policy

This 2-bedroom vacation rental in Greenport allows 1 dog under 20 lbs for no additional fee. Sorry, no cats.

Small Dogs Only

Spacious Apartment 3 Blocks to Downtown

5.0 Greenport, NY

Spacious Apartment 3 Blocks to Downtown Pet Policy

This 2-bedroom apartment in Greenport allows 1 dog under 20 lbs for no additional fee. Sorry, no cats. Non-shedding breeds only. Pets must be crated if left unattended. A crate is provided.

Small Dogs Only

Private Room Near Shore & Beaches

5.0 East Lyme, CT

Private Room Near Shore & Beaches Pet Policy

This 1-bedroom house in East Lyme allows pets in cages for no additional fee. Sorry, no cats or dogs permitted at this property.

Big Dogs Allowed

2+ Pets Allowed

Rustic Lakeside Cabin

5.0 East Lyme, CT

Rustic Lakeside Cabin Pet Policy

This cabin in East Lyme is pet friendly! Dogs of any size are welcome for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

72 Shore Rd

4.8 Clinton, CT

72 Shore Rd Pet Policy

This 2-bedroom vacation rental in Clinton allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

3/2 House with Fire Pit

5.0 Old Saybrook, CT

3/2 House with Fire Pit Pet Policy

This 3-bedroom vacation rental in Old Saybrook allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Casino Wine Down House

4.8 Montville, CT

Casino Wine Down House Pet Policy

This 3-bedroom vacation rental in Montville allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Cove Street Cottage

4.7 Old Saybrook, CT

Cove Street Cottage Pet Policy

This 3-bedroom vacation rental in Old Saybrook allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Big Dogs Allowed

2+ Pets Allowed

Beautiful Madison Beach House

5.0 Madison, CT

Beautiful Madison Beach House Pet Policy

This 4-bedroom vacation rental in Madison allows dogs of any size for a fee of $250 per pet, per stay. Cats may also be allowed by request.

Small Dogs Only

2+ Pets Allowed

Ospreys' Landing

5.0 Old Lyme, CT

Ospreys' Landing Pet Policy

This 1-bedroom vacation rental in Old Lyme allows 2 dogs under 20 lbs for an additional fee of $8 per pet, per night. Cats are also welcome.

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Chester, CT, US