Chatham Vacation Rentals & Apartments - 847 Rentals Available
847 Vacation rentals

Chatham Cape Cod Vacation Rental (13059)
Chatham House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$543.00
from $543.00 / night

16604: < 1 Mile to Cockle Cove Beach! Private, Secluded, Close to Downtown! Dog
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Pet friendly
$130.00
from $130.00 / night

South Chatham Cape Cod Vacation Rental (3388)
Chatham House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$371.00
from $371.00 / night

South Chatham Cape Cod Vacation Rental (2400)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
$414.00
from $414.00 / night

Chatham Cape Cod Vacation Rental (8233)
Chatham House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
South Chatham Cape Cod Vacation Rental (4642)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Chatham Cape Cod Vacation Rental (7102)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Chatham Cape Cod Vacation Rental (1936)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$229.00
from $229.00 / night
Chatham Cape Cod Vacation Rental (2171)
Chatham House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$557.00
from $557.00 / night
South Chatham Cape Cod Vacation Rental (9577)
South Chatham House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$471.00
from $471.00 / night
South Chatham Cape Cod Vacation Rental (4201)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$314.00
from $314.00 / night
Chatham Cape Cod Vacation Rental (2973)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$286.00
from $286.00 / night
Chatham Cape Cod Vacation Rental (4983)
Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$229.00
from $229.00 / night
41 Captains Walk 102234
North Chatham House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
South Chatham Cape Cod Vacation Rental (5025)
Chatham House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 11 11
- 7 nights min
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
South Chatham Cape Cod Vacation Rental (1011)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$457.00
from $457.00 / night
Chatham Cape Cod Vacation Rental (4385)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$557.00
from $557.00 / night
South Chatham Cape Cod Vacation Rental (76)
Chatham House
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$271.00
from $271.00 / night
Chatham Cape Cod Vacation Rental (11498)
Chatham House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$786.00
from $786.00 / night
South Chatham Cape Cod Waterfront Vacation Rental (6972)
Chatham House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$857.00
from $857.00 / night
Chatham Cape Cod Vacation Rental (8716)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$743.00
from $743.00 / night
Chatham Cape Cod Vacation Rental (4489)
Chatham House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$571.00
from $571.00 / night
South Chatham Cape Cod Vacation Rental (7129)
Chatham House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$486.00
from $486.00 / night
South Chatham Cape Cod Waterfront Vacation Rental (4963)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$457.00
from $457.00 / night
West Chatham Cape Cod Waterfront Vacation Rental (20)
Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$221.00
from $221.00 / night
Chatham Cape Cod Vacation Rental (7899)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$486.00
from $486.00 / night
16605: A quaint Cape home only a minute from the most beautiful stretch of beach
Chatham House
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$138.00
from $138.00 / night
South Chatham Cape Cod Vacation Rental (12266)
Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Pet friendly
$157.00
from $157.00 / night
The Snuggery 104507
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
$215.00
from $215.00 / night
Chatham Cape Cod Waterfront Vacation Rental (2172)
Chatham House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$1,907.00
from $1,907.00 / night
South Chatham Cape Cod Vacation Rental (10339)
Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$314.00
from $314.00 / night
Chatham Cape Cod Waterfront Vacation Rental (10325)
Chatham House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Ask about children
- Air conditioning
$800.00
from $800.00 / night
Chatham Cape Cod Waterfront Vacation Rental (12273)
Chatham House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$514.00
from $514.00 / night
South Chatham Cape Cod Vacation Rental (4643)
Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$257.00
from $257.00 / night
South Chatham Cape Cod Vacation Rental (135)
Chatham House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$286.00
from $286.00 / night
16612: Stunning views of Nantucket Sound, wrap around deck, walk to beach!
Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Child friendly
- Pet friendly
$238.00
from $238.00 / night
South Chatham Cape Cod Vacation Rental (3631)
Chatham House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$387.00
from $387.00 / night
15 Bobbies Lane 43070
South Chatham House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$193.00
from $193.00 / night
South Chatham Cape Cod Waterfront Vacation Rental (12574)
Chatham House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$557.00
from $557.00 / night
South Chatham Cape Cod Vacation Rental (30)
South Chatham House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$336.00
from $336.00 / night
About Chatham
Chatham, MA Travel Tips
Attractions
Events
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.
Transit
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.Climate
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.Events
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.Shopping
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.
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.