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Chatham Vacation Rentals

1 - 24 of 24 rentals
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Couple's Paradise by the Sea - Chatham, MA Vacation Rental
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The Sea Chest  in The South of Chatham  - Chatham, MA Vacation Rental
115 115 115 115 115 155 145 - - - - - 145 155 115 - -
A Chatham Pearl on Oyster River - Chatham, MA Vacation Rental
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Waterview Chatham Home  - Chatham, MA Vacation Rental

Waterview Chatham Home

Chatham, MA
2 Bed 1.5 Bath Sleeps 7
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The Place to be... - Provincetown, MA Vacation Rental

The Place to be...

Provincetown, MA
2 Bed 1 Bath Sleeps 5
99 99 99 115 99 - - 99 115 115 115 115 165 165 120 120 120
"Act One"  in Truro - Truro, MA Vacation Rental

"Act One" in Truro

Truro, MA
4 Bed 3 Bath Sleeps 8
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Seaside Park Cottage - Barnstable, MA Vacation Rental

Seaside Park Cottage

Barnstable, MA
3 Bed 2 Bath Sleeps 8
170 170 170 170 170 195 195 170 170 170 170 170 195 195 175 175 175
Bay Side Beauty in Eastham - Eastham, MA Vacation Rental

Bay Side Beauty in Eastham

Eastham, MA
4 Bed 2.5 Bath Sleeps 8
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Harwich Port Perfection - Harwich, MA Vacation Rental

Harwich Port Perfection

Harwich, MA
3 Bed 2.5 Bath Sleeps 8
115 115 115 115 115 155 155 115 115 115 115 115 155 155 120 120 120
Seaview Condo at the Pagodas  - Provincetown, MA Vacation Rental
- - - 85 90 120 120 90 90 90 90 90 120 120 99 99 99
Nauset Beach Buddy  - Orleans, MA Vacation Rental

Nauset Beach Buddy

Orleans, MA
2 Bed 1 Bath Sleeps 4
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Bayside Cape Codder - Dennis, MA Vacation Rental

Bayside Cape Codder

Dennis, MA
3 Bed 2 Bath Sleeps 8
120 120 120 120 120 155 155 120 120 120 120 120 155 155 125 125 125
Escape in Dennis - Dennis, MA Vacation Rental

Escape in Dennis

Dennis, MA
3 Bed 2 Bath Sleeps 7
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The Beauty of Brewster - Brewster, MA Vacation Rental

The Beauty of Brewster

Brewster, MA
4 Bed 2.5 Bath Sleeps 8
125 130 130 130 130 180 180 130 130 130 130 130 180 180 140 140 140
Orleans Oyster Shell - Orleans, MA Vacation Rental

Orleans Oyster Shell

Orleans, MA
3 Bed 2 Bath Sleeps 10
130 130 130 130 130 195 195 130 130 130 130 130 195 195 140 140 140
The Waterfront Penthouse - Provincetown, MA Vacation Rental
- 99 115 130 130 185 185 130 130 130 130 125 - - 135 140 140
Chic Antique in Wellfleet Village - Wellfleet, MA Vacation Rental
130 130 130 130 130 175 175 130 130 130 130 130 175 175 140 140 140
The Boat House on The  Bass River  - Dennis, MA Vacation Rental
99 99 99 99 99 130 130 99 99 99 99 99 130 130 99 99 99
The Beachcomber - Dennis, MA Vacation Rental

The Beachcomber

Dennis, MA
3 Bed 1 Bath Sleeps 7
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Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
220 220 220 170 170 220 220 170 170 170 170 170 220 220 180 180 180
Nauset Beach Dream - Orleans, MA Vacation Rental

Nauset Beach Dream

Orleans, MA
3 Bed 1 Bath Sleeps 6
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Hyannis Port Haven - Hyannis, MA Vacation Rental

Hyannis Port Haven

Hyannis, MA
4 Bed 3 Bath Sleeps 7
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Billingsgate Landing at Wellfleet Harbor - Wellfleet, MA Vacation Rental
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Toes In The Sand at Craigville Beach - Centerville , MA Vacation Rental
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About Chatham

Chatham rated 4.8 out of 5 based on 63 reviews Chatham, MA

Although some of the towns on Cape Cod have lost a bit of their historic charm over the years, Chatham in the Lower Cape has managed to maintain its quaint appeal. With myriad mom-and-pop shops tucked along a pedestrian-friendly and well-maintained main street, Chatham retains its unique allure among Cape towns. And our Chatham vacation rentals allow you to enjoy all the historic sites and Cape Cod flavor while living like a local!

Things to Do in Chatham, MA

Chatham offers plenty of fun for singles, couples, and families alike! Head to the Main Street gazebo for summer concerts featuring local artists. The Cape Cod Baseball League boasts star collegiate players, and the Chatham Anglers are one of its top teams.

Colonial history buffs will be in heaven in Chatham, especially when it comes to historic homes. The Atwood House Museum, built in 1752, is the oldest structure in town and boasts historic documents, vintage tools, a period herb garden and a lighthouse turret. The Caleb Nickerson House, circa 1772, is a classic example of colonial architecture, with wooden wainscoting and pine board floors. The Josiah Mayo House, circa 1820 (and thus downright modern by comparison), transports visitors to the past and celebrates Chatham's first postman.

Had enough of historic homes? The Chatham Railroad Museum sits in the town's railroad depot and boasts locomotives from the 1939 New York World's Fair as well as a wooden caboose from the early 1900s. Or, pay a visit to the cast-iron Chatham Lighthouse, established by Thomas Jefferson, which has protected ships since 1808.

Chatham Beaches & Outdoor Adventures

When you book one of our Cape Cod summer rentals in Chatham, you're never far from the water - and the town offers six saltwater beaches to please everyone in your party. Chatham Lighthouse Beach, with its eponymous historic lighthouse, is the most popular during the warmer months. Harding‘s Beach boasts warmer and calmer waters, due to its position on Nantucket Sound. Schoolhouse Pond and Forest Beach are great for families with small children, and Oyster Pond Beach is conveniently close to town. Dogs are welcome in the early morning and evening on Pleasant Bay Beach (perfect for guests staying in one of our pet-friendly Chatham rentals!), and Pleasant Street Beach is also close to nearby Harwich. After a long day, wash your cares (and sand) away at your Chatham vacation rental.

Day Trips from Chatham

Chatham sits on the Lower Cape and is the perfect gateway to other towns along the coast from Eastham, aka "The Gate", to quaint Harwich to gay-friendly Provincetown. It's also a short drive to Harwich Port to catch the ferry to the picturesque islands of Nantucket and Martha's Vineyard.

Whether historic architecture, windswept beaches, or simply visions of a relaxing weekend getaway draws you here, you'll find a true gem on the Cape when you make one of our Chatham rentals your home-away-from-home!

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