Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Chatham Vacation Rentals

1 - 25 of 25 rentals
  PrevNext  
Sun 26 Mar Mon 27 Mar Tue 28 Mar Wed 29 Mar Thu 30 Mar Fri 31 Mar Sat 1 Apr Sun 2 Apr Mon 3 Apr Tue 4 Apr Wed 5 Apr Thu 6 Apr Fri 7 Apr Sat 8 Apr Sun 9 Apr Mon 10 Apr Tue 11 Apr
Couple's Paradise by the Sea - Chatham, MA Vacation Rental
- - - - - - 120 120 120 120 120 120 150 150 120 120 120
The Sea Chest  in The South of Chatham  - Chatham, MA Vacation Rental
- - - - - - - - 140 150 150 150 180 180 150 150 150
A Chatham Pearl on Oyster River - Chatham, MA Vacation Rental
- - - - - - 155 145 145 145 145 145 190 190 145 145 145
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 99 99 99 99 130 130 99 99 99 99 99 135 135 99 99 99
"Sampsons Folly" - Barnstable, MA Vacation Rental

"Sampsons Folly"

Barnstable, MA
6 Bed 6 Bath Sleeps 14 (8 Adults Max)
290 295 295 295 295 360 360 345 365 365 365 365 445 445 365 365 365
Orleans Oyster Shell - Orleans, MA Vacation Rental

Orleans Oyster Shell

Orleans, MA
3 Bed 2 Bath Sleeps 10
115 120 120 120 120 180 180 130 130 130 130 130 190 190 130 130 130
The Waterfront Penthouse - Provincetown, MA Vacation Rental
- 140 140 140 140 190 190 225 225 225 225 225 240 - - 190 190
The Place to be... - Provincetown, MA Vacation Rental

The Place to be...

Provincetown, MA
2 Bed 1 Bath Sleeps 5
115 120 120 120 120 165 165 115 115 115 115 115 165 165 115 115 115
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
- - - - - - - - - - - - - - - - -
The Beauty of Brewster - Brewster, MA Vacation Rental

The Beauty of Brewster

Brewster, MA
4 Bed 2.5 Bath Sleeps 8
- 120 130 130 130 175 175 135 135 135 135 135 160 - - - -
Seaview Condo at the Pagodas  - Provincetown, MA Vacation Rental
115 120 120 120 120 150 150 99 99 99 99 99 115 115 99 99 99
Harwich Port Perfection - Harwich, MA Vacation Rental

Harwich Port Perfection

Harwich, MA
3 Bed 2.5 Bath Sleeps 8
99 115 115 99 - - - - - 150 160 160 190 190 160 160 160
Bayside Cape Codder - Dennis, MA Vacation Rental

Bayside Cape Codder

Dennis, MA
3 Bed 2 Bath Sleeps 8
- - - - - - - 99 115 115 115 115 150 150 115 115 115
Bay Side Beauty in Eastham - Eastham, MA Vacation Rental

Bay Side Beauty in Eastham

Eastham, MA
4 Bed 2.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
150 155 155 155 155 175 - - - - - - - - - - -
Chic Antique in Wellfleet Village - Wellfleet, MA Vacation Rental
130 135 135 135 135 180 180 130 130 130 130 125 - - - - -
Seaside Park Cottage - Barnstable, MA Vacation Rental

Seaside Park Cottage

Barnstable, MA
3 Bed 2 Bath Sleeps 8
155 160 160 160 160 185 185 135 135 135 135 135 170 170 135 135 135
The Beachcomber - Dennis, MA Vacation Rental

The Beachcomber

Dennis, MA
3 Bed 1 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Nauset Beach Dream - Orleans, MA Vacation Rental

Nauset Beach Dream

Orleans, MA
3 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Boat House on The  Bass River  - Dennis, MA Vacation Rental
99 115 115 115 115 155 155 99 99 99 99 99 130 130 99 99 99
Hyannis Port Haven - Hyannis, MA Vacation Rental

Hyannis Port Haven

Hyannis, MA
4 Bed 3 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
"Act One"  in Truro - Truro, MA Vacation Rental

"Act One" in Truro

Truro, MA
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Billingsgate Landing at Wellfleet Harbor - Wellfleet, MA Vacation Rental
- - - - - - - - - - - - - - - - -
Toes In The Sand at Craigville Beach - Centerville , MA Vacation Rental
- - - - - - - - - - - - - - - - -

About Chatham

Chatham rated 4.8 out of 5 based on 64 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!

  • Searching ...
  • 25 of 25
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here