Chatham Vacation Rentals & Apartments - 283 Rentals Available

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Chatham Home
9 BR / 5 BA / Sleeps 20 9 20 Min stay varies
Home / 9 Bedrooms / Sleeps 20
9 bedrooms 5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"Our family feels so fortunate to have found this beautiful property! My sister was married in early June followed by a gathering in Chatham for a special family reunion. My parents were able to somewhat relax before the wedding, and REALLY relax afterward,..."
- Rhianna Hayes, Boston, MA
(1) Excellent (1 review)
1 / 20

Chatham Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This is a wonderful home in a great Chatham location. Just a few steps to Main Street and Chatham Bars Inn. Newly renovated; equipped with everything we needed; open floor plan on 1st floor with beautifully appointed kitchen, dining area and living..."
- Teresa Waters Servidio, Greenwich, Connecticut
(1) Excellent (1 review)
1 / 1

Chatham Estate
9 BR / 5 BA / Sleeps 20 9 20 7 night min stay
Estate / 9 Bedrooms / Sleeps 20
9 bedrooms 5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"This is a terrific house for a large diverse group (we had 18 people at one time) and three generations. We had plenty of room for all of us, and everyone was comfortable - from grandpa to the 9 month old grand baby. The kids loved the yard, the beach..."
- Katie, Colorado
(1) Excellent (1 review)
1 / 46

Chatham Home
3 BR / 2 BA / Sleeps 10 3 10 Min stay varies
Home / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every day. We traveled up and down the coast, spent a day at Martha's Vineyard,..."
- Carla Smith, Newark, DE
(4) Excellent (4 reviews)
1 / 10

Chatham Cottage
2 BR / 1 BA / Sleeps 5 2 5 7 night min stay
Cottage / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
"We have rented this cottage multiple time. It is on a quiet street with a veiw of the salt marsh; a short walk from the beach. We love to watch the birds and dragon flies and relax."
- Laurie Chadbourne, Amherst, MA USA
(6) Excellent (6 reviews)
1 / 16

Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We really enjoyed our stay in this lovely beach house. Very nice pond, perfect for swimming or fishing. Close to the Ridgevale beach. The house is fully equipped with everything you need and more."
- Jean-Francois Mercier, Johannesburg, South-Africa
(1) Excellent (1 review)
1 / 8

Chatham Home
9 BR / 4 BA / Sleeps 20 9 20 Min stay varies
Home / 9 Bedrooms / Sleeps 20
9 bedrooms 4 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"This house was perfect for our needs. We needed a place which felt like our home at the Cape for so many summers. We had to all be under one roof, sharing stories, memories, laughs & tears. We came to the Cape to sprinkle my husband's ashes at sea...."
- margaret brady, Hudson Valley, New York
(3) Excellent (3 reviews)
1 / 15

Chatham Home
3 BR / 1 BA / Sleeps 5 3 5 Min stay varies
Home / 3 Bedrooms / Sleeps 5
3 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • TV (Antenna)
"The Chatham Retreat measures up to its name. The cottage is clean, quaint, centrally located and a short walk to the beach. This was my third trip there and looking forward to going back again next summer. It is beautifully decorated and well maintained...."
- Donna Somma, NH
(5) Excellent (5 reviews)
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About Chatham

Chatham, MA Travel Tips

Situated on the southeastern tip of Cape Cod is the town of Chatham, MA. This charming town is a pleasant place for families to unwind and spend valuable and fun time together. For the most relaxing experience possible, people will want to skip hotels in favor of Chatham rentals. For the best selection of Chatham vacation rentals online, you're in the right place. Vacation Home Rentals has well-maintained properties available for rent by owner. By booking with us, you can save money and enjoy the comforts of home. When planning a trip to Chatham, there are a few tips that can make the stay more comfortable for all.
During the winter, Chatham is quieter than in the busy summer months. For families that prefer to avoid crowds, this is a good time to visit. Keep an eye on the average temperatures for the month that you'll be visiting Chatham. The warmest months of the year are July and August, with top temperatures averaging 75 degrees Fahrenheit. The coldest month of the year is January, with average lows at 24 degrees Fahrenheit and highs at 38 degrees Fahrenheit. Checking out the weather will help make packing for the family easier. When traveling in peak season, be sure to book Chatham vacation rentals in advance to save time and money.


Rest and relaxation are two of the most important reasons why tourists stay in vacation rentals. Chatham, MA, has so many attractions that at the end of a fun-filled day, families will appreciate a good night's sleep. A popular destination for families is the Atwood House Museum. The museum is a great way to learn about the history of Cape Cod and to view the area's art while staying in Chatham, MA, rentals. Another interesting museum to visit is the Chatham Railroad Museum, which is located in an 1887 railroad depot that has been restored. The Chatham Lighthouse is another popular destination when visiting the city. To visit the lighthouse, tourists may arrange for a tour on dates that have been set aside by the Coast Guard Auxiliary. For many tourists staying in Chatham rentals, the beaches are one of the main attractions. Public beaches include Ridgevale Beach, Harding Beach, Cockle Cove Beach, and more. Parks are another way that families can enjoy their vacation. Parks such as Chase Park offer great outdoor fun and have picnic areas and charcoal grills. Also located in Chatham is the Monomoy National Wildlife Refuge, Samuel Hawes Park, Sears Park, and Volunteer Park.


Hotels are often overcrowded and noisy when the city is hosting a special event. The calm atmosphere and convenience of staying in Chatham, MA, vacation rentals is a benefit for many tourists. Families on vacation will appreciate this convenience and can better enjoy the event's festivities. Festivals, fairs and other events take place throughout the year. In June, for instance, there is the annual Chatham Harbor Run and the Classic Car Invitational. For the children in the family, there are games for kids, while adults can enjoy a beer with their bratwurst and other German fare. Thanksgiving is a great time to travel to and stay in vacation rentals in Chatham, MA. Before indulging in a Thanksgiving Day meal, families can run or walk together in the annual Turkey Trot. Also during the holiday season, don't miss the annual Chatham Christmas Stroll.

When you think of a quaint New England village, of salt shaker houses and quiet, flower-edged lanes, you have Chatham. Though it’s not as sleepy as you might imagine (especially in the summer), a Chatham vacation rental provides the perfect base to explore charming Cape Cod.

Things to Do

The major draw of this area is the beaches. Cape Cod is the place Bostonites and other New Englanders flock to each summer. Cape Cod is to New England populations as Long Island is to New Yorkers. Cockle Cove and Harding’s Beaches provide excellent spots for families, while the Chatham Lighthouse Beach allows visitors to appreciate the nautical history of the area. Lighthouse Beach’s tides are some of the strongest tides in Chatham, so pay attention to posted warnings. The Monomoy National Wildlife Refuge is the ideal place to look for spotted seals and is known for its bird watching.
Seal cruises and fishing jaunts are also popular ways to enjoy the rich gifts of the sea this area is known for. If you go, bring a jacket. The Atlantic and its breezes are cold regardless of the time of year or land temperatures.   


There are a number of buses and shuttle services that take visitors from Boston to Hyannisport and connect them to other points on the cape. During the summer, you can also catch the Cape Flyer, which offers train service from Boston to the Cape. However, most people prefer to bring cars because they can visit all the delightful towns of the cape and have more room than a bike basket provides for their many treasures gathered along the way. Bikes are popular for getting around town from your Chatham vacation rental.


Most people enjoy the cape because it allows them to escape the sweltering heat of the city in the summer. Summer temps are usually in the mid 70s. Winter brings highs in the 30s and can feel bitter due to the dampness off the water.


While winter is the slow time at the cape, it also brings with it the magic of quiet towns and twinkling lights. Chatham hosts a Christmas-by-the-Sea shopping event and a Christmas Stroll as well as many theater shows. July 4th is also a big holiday at the cape as neighboring towns celebrate our nation’s independence with dueling fireworks displays.


Chatham offers a number of darling boutiques and unique shops that feature treasures that are distinctly Cape Cod. From whimsical coastal décor to delightful preppy fashions and candy kitchens with chocolate seashells to works from local artists, you can find the perfect item here to suit your fancy. The stores in Chatham are as adorable as their contents, with awnings and window boxes. Shopping is a real treat in this town.    
A Chatham vacation rental is the perfect way to try on a different style of living; one where bikes with baskets are more popular than what kind of car you drive; where high heels are traded in for sandals; and days are measured in the beauty of experience.