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Chatham Vacation Rentals

1 - 25 of 25 rentals
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The Sea Chest  in The South of Chatham  - Chatham, MA Vacation Rental
115 - - 130 135 135 135 135 175 - - - - - 115 - -
A Chatham Pearl on Oyster River - Chatham, MA Vacation Rental
- - 160 155 190 190 190 190 250 250 190 190 190 190 190 250 250
Couple's Paradise by the Sea - Chatham, MA Vacation Rental
- - - - - - - - - - 130 135 135 135 135 165 165
Cozy Provincetown Getaway - Provincetown, MA Vacation Rental
99 140 140 115 115 115 115 115 160 160 115 115 115 115 115 160 160
Chic Antique in Wellfleet Village - Wellfleet, MA Vacation Rental
- - - - 185 195 195 195 225 225 195 195 195 195 185 - -
The "  B's " Beach Cottage - Dennis, MA Vacation Rental

The " B's " Beach Cottage

Dennis, MA
3 Bed 2 Bath Sleeps 6 (4 Adults Max)
99 130 130 99 115 115 115 115 150 150 115 115 115 115 115 150 150
"Sampsons Folly" - Barnstable, MA Vacation Rental

"Sampsons Folly"

Barnstable, MA
6 Bed 6 Bath Sleeps 14 (8 Adults Max)
- - - - - 385 395 395 485 485 395 395 395 395 395 485 485
Seaview Condo at the Pagodas  - Provincetown, MA Vacation Rental
99 115 115 99 115 115 115 115 160 160 115 115 115 115 115 160 160
The Beauty of Brewster - Brewster, MA Vacation Rental

The Beauty of Brewster

Brewster, MA
4 Bed 2.5 Bath Sleeps 8
- - 150 135 145 145 145 145 195 195 145 145 145 145 145 175 -
Bayside Cape Codder - Dennis, MA Vacation Rental

Bayside Cape Codder

Dennis, MA
3 Bed 2 Bath Sleeps 8
- - - 115 135 135 135 135 175 175 135 135 135 135 130 - -
Seaside Park Cottage - Barnstable, MA Vacation Rental

Seaside Park Cottage

Barnstable, MA
3 Bed 2 Bath Sleeps 8
99 125 - - 130 135 135 135 170 170 135 135 135 135 135 170 160
The Waterfront Penthouse - Provincetown, MA Vacation Rental
- - - 190 225 225 215 - - - - 240 250 250 250 290 -
Orleans Oyster Shell - Orleans, MA Vacation Rental

Orleans Oyster Shell

Orleans, MA
3 Bed 2 Bath Sleeps 10
130 190 190 135 135 135 135 135 195 195 135 135 135 135 135 195 195
The Place to be... - Provincetown, MA Vacation Rental

The Place to be...

Provincetown, MA
2 Bed 1 Bath Sleeps 5
99 135 135 99 115 115 115 115 155 155 115 115 115 115 115 155 155
Nauset Beach Buddy  - Orleans, MA Vacation Rental

Nauset Beach Buddy

Orleans, MA
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Escape in Dennis - Dennis, MA Vacation Rental

Escape in Dennis

Dennis, MA
3 Bed 2 Bath Sleeps 7
- - - 90 90 90 90 90 115 115 90 90 90 90 90 115 115
Harwich Port Perfection - Harwich, MA Vacation Rental

Harwich Port Perfection

Harwich, MA
3 Bed 2.5 Bath Sleeps 8
150 180 180 160 160 160 160 160 195 195 160 160 160 160 160 195 195
Nauset Beach Dream - Orleans, MA Vacation Rental

Nauset Beach Dream

Orleans, MA
3 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
- - - - - - - - - - - - - - - - -
The Boat House on The  Bass River  - Dennis, MA Vacation Rental
- - - - - - - - - - - - - - - - -
Hyannis Port Haven - Hyannis, MA Vacation Rental

Hyannis Port Haven

Hyannis, MA
4 Bed 3 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Bay Side Beauty in Eastham - Eastham, MA Vacation Rental

Bay Side Beauty in Eastham

Eastham, MA
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
"Act One"  in Truro - Truro, MA Vacation Rental

"Act One" in Truro

Truro, MA
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
The Beachcomber - Dennis, MA Vacation Rental

The Beachcomber

Dennis, MA
3 Bed 1 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Billingsgate Landing at Wellfleet Harbor - Wellfleet, MA Vacation Rental
- - - - - - - - - - - - - - - - -

About Chatham

Chatham rated 4.8 out of 5 based on 66 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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