Top Winter Vacations - Vacation Rentals in Caleb Nickerson House

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From US $491

         

10.0 (117 Reviews)

House

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $908

         

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10.0 (6 Reviews)

House

1 Mile from Downtown Chatham Walk to Pier

• Air Conditioner
• Parking
• View

• Massachusetts
• Chatham

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From US $502

         

|

9.8 (214 Reviews)

Bed & Breakfast

Captain's House Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $416

         

9.6 (24 Reviews)

House

Lovely Home Minutes from Beach in Chatham!

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $713

         

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10.0 (3 Reviews)

House

Central AC Close to Beach Dog Friendly!

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $342

         

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9.6 (162 Reviews)

Bed & Breakfast

Old Harbor Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $834

         

10.0 (129 Reviews)

House

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $515

         

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10.0 (3 Reviews)

House

Fully Updated Home w Great Outdoor Space

• Air Conditioner
• Parking
• View

• Massachusetts
• South Chatham

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From US $229

         

8.0 (159 Reviews)

Bed & Breakfast

Surfside Inn Chatham

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $675

         

10.0 (102 Reviews)

House

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $523

         

10.0 (100 Reviews)

House

See the World Cup AND Enjoy a Chatham Vacation June 2026

• Air Conditioner
• Parking
• TV

• Chatham
• West Chatham

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From US $2,260

         

10.0 (42 Reviews)

House

5-bedroom vacation home just 3 minutes drive to Cape Cod Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $555

         

9.6 (55 Reviews)

House

Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $401

         

10.0 (19 Reviews)

Cottage

Waterfront Chatham Retreat w/WiFi & Privacy

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $675

         

9.4 (25 Reviews)

House

1 Mi to Beach: Home w/Fire Pit & BBQ in Cape Cod!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• South Chatham

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From US $505

         

9.8 (46 Reviews)

House

Secluded Chatham Cape Cod House Stage Harbor Area

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $517

         

9.6 (8 Reviews)

House

The Cape Escape: Walk to Harding's Beach

• Air Conditioner
• Parking
• Pet Friendly

• Chatham
• West Chatham

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From US $292

         

9.4 (66 Reviews)

Apartment

Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home

• Air Conditioner
• Parking
• TV

• Massachusetts
• Chatham

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From US $611

         

10.0 (6 Reviews)

House

Beachside Bliss: Dog Friendly & Breezy Stay

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• South Chatham

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From US $592

         

10.0 (27 Reviews)

House

Sleeps 10+/Walk To Buck's Pond Lake! Close To Beach/Golf/Restaurants

• Air Conditioner
• Parking
• TV

• Harwich
• East Harwich

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From US $336

         

10.0 (7 Reviews)

House

Beach Days Await at Harwich Getaway

• Air Conditioner
• Parking
• TV

• Harwich
• East Harwich

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From US $373

         

9.4 (13 Reviews)

House

Chatham Home Near the Bike Trail & Nantucket Sound (1524)

• Air Conditioner
• Parking
• TV

• Massachusetts
• South Chatham

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From US $405

         

8.8 (27 Reviews)

House

Pet friendly home with central air (1998)

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Chatham

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From US $2,102

         

10.0 (19 Reviews)

House

Beam Reach: 137-O Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool

• Air Conditioner
• Parking
• Pet Friendly

• Orleans
• South Orleans

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