Owner Direct Vacation
Rentals in Chatham

There are a lot of options in Chatham. If you plan on staying in the Chatham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chatham:

• Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
• Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
• Chatham walk to Cape Cod beach
• Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
• Water View-Walk town/beach, pets considered, Linen Option
• Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
• Cape Cod Chatham Water View Retreat
• Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
• 5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
• Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

There are 36 vacation rentals with private pools near Chatham. Top-rated homes that have access to a swimming pool include:

• Eileen's Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated
• Sophisticated Chatham Retreat with Private Pool and Spa RPAM093
• Plunge Pool, Game Barn, AC, 5 Min to Beach!
• Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

If you are looking for a family-friendly vacation home in Chatham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chatham:

• Lovely Home Minutes from Beach in Chatham
• Outermost Waterfront Chatham Home w/Wraparound Views
• Surfside Inn Chatham

Currently, the total number of properties listed in 2026 is over 680 in the Chatham area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chatham.