1,187 Chatham Holiday Rentals

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Compare Chatham holiday rentals from 10 rental sites including HomeAway, TripAdvisor, WeNeedAVacation and more, ranging from $34 to $28571 a night.

Information about Chatham

Information about Chatham

A seaside town on the southeastern tip of the Cape Cod peninsula of Massachusetts, Chatham is a popular tourist destination in the summer, when the population grows from 6,100 to roughly 30,000. Harwich borders the town to both the north and west boundary lines, while the Atlantic Ocean, the Nantucket Sound and Pleasant Bay border the rest of Chatham. Retirees and tourists enjoy Chatham for its seaside environment and seclusion from big cities.

Samuel de Champlain discovered Chatham in 1606, and the town was settled by the English in 1664, having previously been habituated by the Monomoy people. At the end of the 1800s, wealthy visitors began to vacation in Chatham during the summer. The economy grew, and the townspeople founded a newspaper and instated telephone service. In 1930, Chatham saw its first airport, and summer tourism steadily increased. Along with other popular tourist destinations in Cape Cod, Chatham is now a summer hotspot for vacationers.

Things to Do in Chatham

A thriving resort town, Chatham boasts several excellent beaches. Ridgevale Beach is among the most popular, offering prime conditions for water sports as well as calmer tide pools for children. Other popular beaches include the picturesque Chatham Lighthouse Beach and Harding Beach. Keep an eye out for seals and other wildlife!

The U.S. Air Force briefly used Monomoy Island off the coast of Chatham for gun range practice before the land was repurposed in 1951. Now, it’s home to The Monomoy National Refuge, a habitat for birds and various varieties of marshes, dunes and ponds. Visit the lighthouse on the island to take a peek inside the keeper’s quarters.

Built in 1916 and restored in 2011, the Orpheum Theater has been an entertainment destination for many generations of Chatham residents and visitors. The Orpheum showcases blockbuster hits as well as indie flicks on its two screens. If the weather isn’t suitable for outside play, grab a popcorn or a plate of local cuisine from the theater café and enjoy a movie!

Chatham Day Trips

Take a boat from Harwich Port to Nantucket Island, a small and secluded island filled with dunes, boutiques, and cobblestone streets. It’s roughly a 30-mile trip by ferry. Visit the lighthouses and historic buildings to see why the National Park Service calls Nantucket “the finest surviving architectural and environmental example of a late 18th- and early 19th-century New England seaport town.”

From Nantucket, you can also take a ferry to Martha’s Vineyard – host of such esteemed visitors as the Kennedys, the Clintons and the Obamas. The island, which is famous for its lovely vacationing weather and breathtaking beaches, was the filming site for the movie Jaws. Summers and weekends can be crowded on the island, so visit during the day and spend the night back in Chatham.

Those looking for a day-long fishing trip are encouraged to check out Pleasant Bay. The bay, which borders Chatham to the north, is an eight-mile passage that can be navigated by a small boat. Many of Pleasant Bay’s fishing access points are private, but follow Strong Island Road to a small parking area and beach at the end of the road for a public fishing spot. Those not interested in fishing can also kayak in the bay’s various channels – but be sure to bring along a map or a guide!

Chatham Accommodations

Tripping.com offers almost 800 rentals in Chatham. Are you taking a pet along on vacation? Check out one of Tripping.com’s pet-friendly rental spaces! For those who need to stay connected, Wi-Fi is available in more than half of Tripping.com’s Chatham rentals.

If you’re looking to make your stay in Chatham as cozy as possible, find one of over 100 rentals with a fireplace to help make this seaside destination your home away from home. Be sure to look out for properties marked “Instabook,” which can be booked immediately.

Choose a rental on the east side of Chatham if you’d like an ocean view. If you stay near the “elbow” of Cape Cod, you might even be able to walk to the historic Chatham Lighthouse! If you pick a spot in North Chatham, you’ll be in close proximity to the Chatham Pier Fish Market, a great spot to buy lobster or watch the boats roll in from the Atlantic Ocean and Pleasant Bay.

Chatham Transportation

Rent a car, bike around the town, or hop on a train or bus in Chatham. Bus stops are few and far between within the city limits, but drivers will stop if you catch their attention. Buses are equipped with ramps and bicycle racks.

The CapeFLYER train offers service throughout the summer between Cape Cod and Boston. You can bring bikes on the train at no charge. The Chatham Municipal Airport is a very small (but full service) airport on the northwest side of town.

Head to Hyannis for alternative air transit at the Barnstable Municipal Airport. Hyannis also offers a ferry to nearby islands.

Vacation Rentals in Chatham

Find the best Chatham vacation rentals with Tripping.com. Choose from 4181 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $34 a night to $28571 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 3285 of homes in Chatham offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 331 rentals with pool or jacuzzi, or relax with the family in one of the 3326 homes with cable TV.

For all those dog lovers and cat lovers, Chatham offers 539 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 10 rental sites in Chatham where the top providers in that area are HomeAway, TripAdvisor, and WeNeedAVacation. There are 1436 HomeAway rentals, 1312 TripAdvisor short term rentals and 896 WeNeedAVacation vacation rentals.