Contact Us

Chatham Cape Cod Vacation Rentals

There are plenty of activities and things to do in and around Chatham for vacationing families.
For beach goers there are Cockle Cove and Ridgevale Beaches. Golfers will enjoy the scenic, nine hole Chatham Seaside Links and the 36 hole Captains Golf Course is in nearby Brewster. Day trips for whale watching and deep sea fishing are also close by. A branch of the  Cape Cod Rail Trail begins in Chatham and extends to Dennis at one end and Wellfleet at the other. Baseball fans will enjoy watching a Chatham Anglers game against an opposing team of the Cape Cod Baseball Leage. There are many family and fine dining restaurants to choose from and an assortment of antique and speciality shops. Stop in town for a bite to eat or a beverage after a day on the beach or out on a boat.
For more activities, please visit our Things To Do page.

Search Results

Found 21 properties

Beautifully Maintained 3BR Colonial Close to Forrest Beach

$2200/week

South Chatham | #1577
3 BR | 2 Baths | Sleeps 8

This rental is a comfortable 3 bedroom, 2 bath that sleeps 8. It sits on a pretty lot with a big backyard just 7/10th of a mile to Forest Beach in Chatham.

View Details

Cape 3BR Home Close to Pleasant Bay

$2500-3000/week

Chatham | #1978
3 BR | 2.5 Baths | Sleeps 8

This 3 bedroom cottage is the perfect location for your family stay in Chatham. You can't beat the location less than a mile away from Jackknife Beach on Pleasant Bay, 2.5 miles to downtown Chatham and Oyster Pond Beach.

View Details

Add to my favorites!
Chatham Beach Compound

Chatham Beach Compound

$6500/week

Chatham | #RP9216
3 BR | 2 Baths | Sleeps 6

Located in the highly desirable Morris Island area

View Details

Chatham Beach Facing 2 Bedroom Condo With Private Beach Access

$2250-3000/week

Chatham | #2267
2 BR | 2 Baths | Sleeps 6

Stunning two bedroom condo overlooking the Chatham beach and Outemost Harbor.

View Details

Add to my favorites!
Chatham Emery Pond

Chatham Emery Pond

$3750/week

Chatham | #RP9041
5 BR | 3 Baths | Sleeps 12

Centrally Located Chatham Rental with Amenities

View Details

Cozy South Chatham Vacation Cottage

$1800-2850/week

South Chatham | #2079
4 BR | 2 Baths | Sleeps 8

This cozy South Chatham vacation cottage is located in a seaside neighborhood, close to the Chatham Beaches on Nantucket Sound and enticing local restaurants and shops.

View Details

Cute Cottage - Half Mile to Nantucket Sound!

$1585/week

South Chatham | #1976
2 BR | 1 Baths | Sleeps 6

Perfect for a relaxing vacation. Located in a quiet location in South Chatham, only ½ mile to Nantucket Sound.

View Details

Enjoy your own PRIVATE POOL in Chatham!

$4999-5999/week

Chatham | #2252
5 BR | 2.5 Baths | Sleeps 12

A private and spacious backyard with a pool includes the ultimate accessories for a fabulous vacation guaranteed to make sure you leave feeling relaxed and fulfilled!

View Details

Explore Chatham's Nantucket Sound Beaches!

$950-1499/week

South Chatham | #2037
2 BR | 2 Baths | Sleeps 6

Conveniently located in South Chatham. This lovely Townhouse is close to some of Chatham's best swimming beaches.

View Details

Add to my favorites!
Harding's Beach

Harding's Beach

$4200/week

Chatham | #RP9118
4 BR | 2 Baths | Sleeps 10

Renovated with back deck & outdoor shower. Stroll to the beach.

View Details

Heated pool and breathtaking views!

$14000-16000/week

Chatham | #RP9033
4 BR | 6 Baths | Sleeps 8

Sophisticated Contemporary Overlooking Chatham Pier Heated Pool and Hot Tub in Resort Luxury Setting.

View Details

Add to my favorites!
Historic Chatham Home

Historic Chatham Home

$30000/week

Chatham | #RP9119
7 BR | 5 Baths | Sleeps 16

Robert Paul Properties

View Details

Lovely Chatham Home Near the Bike Trail

$1500-2100/week

South Chatham | #1524
3 BR | 2 Baths | Sleeps 6

Enjoy this 3-bedroom, 2 bath contemporary Chatham home just minutes from the Cape Cod Rail Trail for great cycling and 1 mile to the beautiful beaches on Nantucket Sound.

View Details

North Chatham - Charming "Stones Throw"

$2000-3500/week

Chatham | #2130
4 BR | 2 Baths | Sleeps 8

Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom.

View Details

Add to my favorites!
On the water with amazing views!

On the water with amazing views!

$5000-7200/week

Chatham | #RP9018
4 BR | 3 Baths | Sleeps 10

Home on Oyster River Close to Hardings beach.

View Details

Perfectly Located 3 Bedroom Chatham Charmer

$3900-4500/week

North Chatham | #RP9178
3 BR | 2 Baths | Sleeps 8

Location is everything! The perfectly appointed 3 bed, 2 full bath home is just 1.3 miles to Chatham Main Street

View Details

Add to my favorites!
Pet Friendly & Close to Trails

Pet Friendly & Close to Trails

$6000/week

Chatham | #RP9023
5 BR | 5.5 Baths | Sleeps 12

Pet Friendly Luxury Rental

View Details

Pet friendly home with central air

$1790-1945/week

Chatham | #1998
4 BR | 2 Baths | Sleeps 8

This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh water ponds and just a short drive to Pleasant Bay!

View Details

Pool and Private Association Beach In Cannon Hill

$9500-12500/week

North Chatham | #RP9015
4 BR | 3.5 Baths | Sleeps 10

4 BED / 3.5 BATH / SLEEPS 10 w/ HEATED POOL AND ASSOCIATION BEACH.

View Details

Add to my favorites!
Prime Morris Island

Prime Morris Island

$5000/week

Chatham | #RP9217
2 BR | 1 Baths | Sleeps 2

Featuring direct beach access to one of the most stunning Cape Cod waterfronts

View Details