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Latest Vacation Rentals in Chatham MA (25)

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8 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Tennis anyone? This stately home with 8 bedrooms, can sleep 18 with 3 kings, 2 queens, 5 twins and 8 doubles in custom built in bunk beds. 8 full baths, and 2 half baths. A deck overlooks the...

Created Apr 14, 2024

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2 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachusetts. Fresh and new, the Townhome also includes access to a swimming pool and...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Comfy and cozy four bedroom home near Hardings Beach! This recently updated Cape cottage is filled with new furnishings, and is a wonderful spot for your vacation in Chatham. There is a deeded foot...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's coveted downtown shopping and dining scene. Welcome to 25 Spring Hill Rd a light-...

Created Apr 14, 2024

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1 Br Cottage Vacation Rental In Chatham, Massachusetts

Spend your vacation in The Sea Crest! This sweet clapboard cottage on the hill off Stage Harbor Road offers an open kitchen, living area, and a queen size bed. Crispy white tones and pops of color...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

A beautiful house on a quiet cul-de-sac that is close to everything that Chatham has to offer. It is less than 2 miles from the many wonderful beaches! If you love to ride bikes, the Cape Cod Rail...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Whale's TalesOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You couldnt ask for a sweeter stay than this...

Created Apr 14, 2024

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2 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

B By the SeaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Walk to Oyster Pond and downtown! This renovated,...

Created Apr 14, 2024

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5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Absolutely beautiful vacation home with upscale furnishings throughout! Giant wraparound porch complete with comfy furniture and central air conditioning (Two zones). The kitchen is a chef's dream,...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

This renovated, clean home is your perfect home away from home. Set back from Route 28 (Main Street) on 1.8 private acres abutting conservation land and a Cape Cod kettle pond, this retreat...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, next to everything. Relax in the professionally designed beach motif that is...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Location, Location, Location New to the rental market, this fully renovated centrally located cape home checks all the boxes. Within minutes you can walk to some of Chatham's top attractions...

Created Apr 14, 2024

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2 Br Cottage Vacation Rental In Chatham, Massachusetts

Oh Buoy Oh BuoyEscape to Oh Buoy Oh Buoy, our tastefully renovated Chatham cottage just one mile from the soft, white sand and warm waters of Hardings Beach. Nestled on a quiet cul-de-sac, this...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Summary:16646 - Sunny-Side-Up: Deeded Rights to Emery Pond Fire Pit!The Space:Spend a week where the sun always shines at our Chatham family home that sleeps 6, and enjoy the best Bs of Summer on...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Harding's and that connects to Lighthouse Beach. It's close enough to return home...

Created Apr 14, 2024

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5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

***KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED! OPEN YEAR ROUNDSpacious five bedroom, four bath home in charming Riverbay Estates overlooking Monomoy River, also known as Muddy...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our beach home has been lovingly furnished, decorated and updated. The open...

Created Apr 14, 2024

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Private Vacation Home Vacation Rental In Chatham, Massachusetts

This lovely home is just steps to Chatham Windmill, Chase Park, Chatham Village and Oyster Pond Beach. It offers two living areas on the main floor, as well as a full bath and a master bedroom. The...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Check in to this beautifully renovated West Chatham ranch, located south of 28 on a quiet cul-de-sac perfect for families to relax and unwind after a day at one of Chatham's many pristine beaches....

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. Our home is 1/2 mile from the quaint town center and Oyster Pond, and 1/4 mile walk to the children's playground...

Created Apr 14, 2024

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1 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

3 Bedroom- 3.5 Bathrooms- Sleeps 10A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off...

Created Apr 14, 2024

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4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

This property is professionally managed by Pretty Picky PropertiesExquisite Chatham Home, Easy Access to Town, Bike TrailNew Heated Salt Water Pool to be installed for 2024!Rents Friday to Friday...

Created Apr 14, 2024

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3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts

Every room in this year-round home has been totally renovated and redesigned just a few years ago. Bayview Cottage features central air conditioning throughout, gleaming hardwood floors in living...

Created Apr 14, 2024

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