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Cape Cod Rentals Featuring: Chatham MA

Explore the beauty, history, and waterways of Cape Cod when you stay in one of our Chatham vacation rentals. After a long day in nature, or antique shopping, enjoy dining at one of the local breweries, and the best ice cream for dessert.

For the best guaranteed rate, browse the available Cape Cod vacation rentals below and book online today!

Explore the beauty, history, and waterways of Cape Cod when you stay in one of our Chatham vacation rentals. After a long day in nature, or antique shopping, enjoy dining at one of the local breweries, and the best ice cream for dessert. For the best guaranteed rate, browse the available Cape Cod vacation rentals below and book online today!
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19 Properties Returned
3 Bed
3 Bath
Sleep 8

Enjoy your stay in the charming Chatham home~ beautiful water views and close proximity to Main Street Chatham...

3 Bed
2 Bath
Sleep 8

This bright, exceptionally clean, relaxing cape style home is only a 5 to 7 minute stroll to Pleasant Street Beach, a natural beach on the warm waters of Nantucket Sound....

2 Bed
1½ Bath
Sleep 4

Inviting, comfortable and upbeat best describes this 2BR/1.5BA cottage right on Mill Pond....

4 Bed
2½ Bath
Sleep 8

This updated home offers Central A/C, WIFI and a fenced in yard. Enjoy Coastal decor and a spacious open floor plan and inviting deck for your relaxation!...

3 Bed
2½ Bath
Sleep 6

This bright and clean home in Chatham is the perfect blend of Cape Cod charm and elegance....

2 Bed
2 Bath
Sleep 7

Classic and comfortable in its decor and design, this home in Chatham provides the quintessential summer experience on Cape Cod....

6 Bed
2 Bath
Sleep 11

You won't want to miss this charming 6 Bedroom, 2 Bathroom home in the heart of Chatham!...

4 Bed
2 Bath
Sleep 6

Set high on a knoll in prestigious North Chatham, Quisisana neighborhood with distant views of Chatham Harbor....

3 Bed
2 Bath
Sleep 6

Conveniently located and beautifully updated, this Chatham getaway is the perfect spot for your summer vacation. The entire property is very well-maintained, and you will enjoy all the comforts of home in this cute and cozy escape!...

3 Bed
2½ Bath
Sleep 8

Sophisticatedly furnished and well maintained 3BR/2.5BA Cape style home accessible to Lovers Lake!...

3 Bed
2½ Bath
Sleep 8

Deeded Rights to White Pond! This 3-bedroom, 2 bath meticulously maintained, open concept, cape style home adjacent to White Pond is next to the bike path, is in a cul-de-sac neighborhood and is close to the village!...

3 Bed
3½ Bath
Sleep 8

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3 Bed
2 Bath
Sleep 8

Great location in a highly desirable area. Beautiful Chatham home with views of the water....

3 Bed
2 Bath
Sleep 7

Enjoy your summer vacation at this cozy and conveniently located Chatham home....

2 Bed
2 Bath
Sleep 6

Looking to enjoy the natural beauty of Cape Cod without having to leave your home? Welcome to Lake Therapy!...

4 Bed
2½ Bath
Sleep 8

A gem in Chatham! This "Upside Down" split level home is just what the doctor ordered to turn you "Rightside Up" again!...

4 Bed
2 Bath
Sleep 8

Looking for the perfect home for your next Chatham vacation?...

3 Bed
2 Bath
Sleep 6

Don't forget about sunny summer days and look forward to the crisp cool fall evenings. This tastefully coastal furnished home provides the essentials for a fabulous vacation....