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From $382 per night (USD)
VRBO
On the Chatham Loop - 1 Min to the Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: 16619 - Chatham Cruiser: On the Chatham Loop - 1 Min to the Beach! The Space: Chatham Cruiser is the perfect m ...
From $382 per night (USD)
VRBO
From $854 per night (USD)
Expedia
Chatham-Walk to Town/Beach-Multi Family Friendly
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
It's all about location. You will have the perfect family vacation in this 5 bedroom, 4.5 bath bathroom lovingly cared ...
From $854 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy your vacation at this lovely North Chatham home. This charming, sunny and spacious, arts and crafts bungalow is co ...
From $658 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Chatham Village - Adorable Studio Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $212 per night (USD)
Expedia
From $608 per night (USD)
VRBO
Newly updated home sleeps 7, AC, free WIFI, half mile to town
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 Bedroom - 2 Baths - Sleeps 7 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $608 per night (USD)
VRBO
From $594 per night (USD)
Expedia
1 Mile from Downtown Chatham Walk to Pier
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16655 - Riptide: 1 Mile from Downtown Chatham Walk to Pier The Space: One of the many perks of staying at this ...
From $594 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Dog-Friendly Home w/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Seashell Wishes-Salty Kisses Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $188 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Pond Front Home w/ Game Room Dog Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16636 - Canoe Club: Pond Front Home w/ Game Room Dog Friendly! The Space: Awake to water views and enjoy your ...
From $409 per night (USD)
Expedia
From $622 per night (USD)
VRBO
Perfect for Group w/ Kids & Dogs w/ Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16638 - The Flying Fish: Perfect for Group w/ Kids & Dogs w/ Hot Tub The Space: Are you searching for a recent ...
From $622 per night (USD)
VRBO
From $628 per night (USD)
Expedia
GREAT LOCATION - Water View, Walk to beach & Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location, Location, Location! Enjoy all the Chatham has to offer! Views of Claflin Landing Beach, Chatham Harbor, No ...
From $628 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $263 per night (USD)
VRBO
From $625 per night (USD)
Expedia
4 Bedrooms, 2 Baths, Sleeps 8-10
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Location! Location! Location! The “Woodford Reserve” for fun and respite! This is classic cape cod home with four bedro ...
From $625 per night (USD)
Expedia
From $815 per night (USD)
VRBO
Fantastically located Chatham house - DISCOUNTED - New patio, refurbished
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Location of the House - Highly sought after Chatham house - corner property which is a walking distance from Historic Do ...
From $815 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Comfort and charm abound in this updated 18th Century seaside farmhouse (4 bedrooms and 3 baths!) situated on more than ...
From $647 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Chatham Beach Chic 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
You will begin to relax the moment you settle into this private family beach retreat. Newly renovated kitchen with quar ...
From $469 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Chatham Village - Lovely 2 bedroom apartment in the antique home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $382 per night (USD)
Expedia
From $983 per night (USD)
VRBO
Steps to Oyster Pond Private Dock!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Summary: 16656 - Decked Out Oyster: Steps to Oyster Pond Private Dock! The Space: Calling all water enthusiasts! This s ...
From $983 per night (USD)
VRBO
Click For Pricing
Expedia
Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Beautifully renovated in 2020, this historic Chatham home is steps away from Lighthouse Beach. Bright and airy, the ope ...
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Expedia
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VRBO
Blue water views and coral sunsets from every room in this beautifully appointed home.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the charm of Chatham in this beautifully appointed rental, perfectly situated with stunning views of Oyster P ...
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VRBO
From $372 per night (USD)
Expedia
This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the charm of downtown Chatham from this cozy rental! You'll be just a short walk from Oyster Pond, perfect fo ...
From $372 per night (USD)
Expedia
From $2518 per night (USD)
VRBO
Tennis anyone? Beautiful, brand new construction with 8 bedrooms, 8 full baths and 2 half baths, that can sleep up to 20 guests.
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
Are you ready for tennis? This stately home features 8 bedrooms and can accommodate 18 guests, with 3 king beds, 2 queen ...
From $2518 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Beautiful home overlooking Emery Pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful home overlooking Emery Pond offers a spacious layout with 2 bedrooms and 1.5 baths, comfortably accommoda ...
From $552 per night (USD)
Expedia
Click For Pricing
VRBO
Quaint Cottage near Rail Trail & Downtown Chatham.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Quaint 2 bedroom home on quiet street. Cozy and comfortable with lots of extra sleeping space available in partially fin ...
Click For Pricing
VRBO
From $1344 per night (USD)
Expedia
School Street in the Old Village!! Charming, new construction with attention to detail!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover the charm of this home on sought after School Street! This stunning 4 bedroom property features a flexible slee ...
From $1344 per night (USD)
Expedia
From $711 per night (USD)
VRBO
Charming house located in the heart of downtown Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming house, with a shared driveway, is located in the heart of downtown Chatham. Leave your cars parked and a s ...
From $711 per night (USD)
VRBO
From $744 per night (USD)
Expedia
5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Chatham Beach House with deeded rights to a path to Hardings Beach as well as to a path to Oyster River Boatyard. Five ...
From $744 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $252 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Chatham Pearl on Oyster River Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $255 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Newly Open - Aug 23-30!! Spacious 3 BR with AC. Walk to Beach! Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming, air-conditioned Chatham home has recently been upgraded. It has new living room furniture and fresh paint ...
From $509 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Wonderful cottage located in the heart of downtown Chatham......steps to everything.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to downtown Chatham! This serene spot in the heart of the village is just a short walk from Main Street's shops, ...
From $577 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Walk to private beach, central air, wifi, 3 bedrooms.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Smell the water! Fully renovated, three-bedroom, two-bathroom Nantucket style home. Walk to private beach on a dead-end ...
From $524 per night (USD)
VRBO
From $468 per night (USD)
Expedia
A well-appointed getaway near beach, Wifi, Gas grill, Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chatham Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $468 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Fantastic location! Thoughtfully updated with all new furnishings! Beautiful light filled 2 bedroom, 2 bath second floo ...
From $479 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
B By the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $341 per night (USD)
Expedia
From $1783 per night (USD)
VRBO
Updated Chatham Inn Home | Spacious Deck & Private Heated Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Stepping Stones -- Old Chatham Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $1783 per night (USD)
VRBO
From $227 per night (USD)
Expedia
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming Downtown Chatham Condo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $227 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Waterfront house on Bucks Creek Marsh with deck, dock, & kayaks
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Magnificent Salt Waterfront with Sunset & Views Our calendar is updated in real-time & our nightly rates are accuratel ...
From $619 per night (USD)
VRBO
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Expedia
Waterfront on Pleasant Bay with stunning views
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Waterfront! Enjoy your Chatham vacation at this stunning 5 bedroom 4 and 1 half bath home in North Chatham. Situated on ...
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Expedia
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VRBO
Step back in time in this beautifully maintained antique horse barn cottage!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Step back in time and experience the charm of this beautifully maintained antique carriage house, comfortably accommodat ...
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VRBO
From $321 per night (USD)
Expedia
Sweet clapboard cottage that is walk to the beach and downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to The Sea Crest for your next vacation! This charming clapboard cottage, perched on a hill off Stage Harbor Road ...
From $321 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Cute clapboard cottage on the hill off Stage Island Road!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spend your vacation in The Sand Dune! This cute clapboard cottage on the hill off Stage Island Road offers an open kitch ...
From $321 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Colorful clapboard cottage perfect for 2!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to The Sea Glass for your next vacation! This charming clapboard cottage, perched on a hill off Stage Harbor Road ...
From $284 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Just off the Chatham bike loop... a perfect location for your family vacation.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just off the Chatham loop, this two bedroom home is the perfect spot for your family vacation. It features a que ...
From $599 per night (USD)
VRBO
From $355 per night (USD)
Expedia
5-Mins to Forest Beach Dog Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16647 - Pink Sky : 5-Mins to Forest Beach Dog Friendly! The Space: Escape the hustle and bustle of your everyd ...
From $355 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Newly Renovated Modern Pond Access!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16622 - The Yachtsman: Newly Renovated Modern Pond Access! The Space: Fully updated and modernized, this vacat ...
From $513 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Wrap-Around Porch Mins. to Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 16643 - Tidal Treasure: Wrap-Around Porch Mins. to Beach! The Space: There isn’t a much more beautiful place t ...
From $285 per night (USD)
Expedia
From $581 per night (USD)
VRBO
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air ...
From $581 per night (USD)
VRBO
From $356 per night (USD)
VRBO
1 Mi to Town & Oyster Pond Beach: Chatham Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $356 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $315 per night (USD)
VRBO
From $853 per night (USD)
Expedia
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Ocean Harbor Waterfront. Stunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with ...
From $853 per night (USD)
Expedia
From $436 per night (USD)
VRBO
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the sh ...
From $436 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Sunrise to Sunset: Bucks Creek Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $590 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Spacious Home on the Loop in Chatham
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Located on the Loop in scenic Chatham, this house rents Sunday to Sunday. The large living room opens onto a deck with ...
From $755 per night (USD)
VRBO
From $347 per night (USD)
VRBO
~ 4 Mi to Dtwn: Chatham Home w/ Fire Pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1,802 Sq Ft | Furnished Deck w/ Gas Grill | Fireplace | 13 Mi to Whydah Pirate Museum Welcome to the good life! Whether ...
From $347 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Full Renovation! Amazing Spot with Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16620 - A Step Above: Full Renovation! Amazing Spot with Views! The Space: Our completely renovated and newly ...
From $419 per night (USD)
VRBO
From $879 per night (USD)
Expedia
Pet friendly and spacious home in quiet neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $879 per night (USD)
Expedia
From $752 per night (USD)
VRBO
Beautiful Home w/ Artistic Flair!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: 16657 - Artist's Haven: Beautiful Home w/ Artistic Flair! The Space: On the Cul-de-sac of a private Chatham ne ...
From $752 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Centrally Located Home w/ Patio Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: 16658 - Home Base: Centrally Located Home w/ Patio Fire Pit! The Space: Conveniently situated in the middle of ...
From $647 per night (USD)
Expedia
From $463 per night (USD)
VRBO
North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1 Bathroom - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $463 per night (USD)
VRBO
Click For Pricing
Expedia
Vacation in downtown Chatham close to Lighthouse Beach
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Spend your Cape Cod vacation in this rental perfectly situated in the heart of downtown Chatham. We're just a half-mile ...
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Expedia
From $1163 per night (USD)
VRBO
Location and Luxury
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Har ...
From $1163 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Chatham walk to Cape Cod beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A Very Short Walk to Hardings Beach. Ocean-side private neighborhood. Chosen by Condé Nast Traveler as “One of the Bes ...
From $515 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Charming Downtown Chatham
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Charming in town apartment above retail shops overlooks the Main St. Walk to beaches, nearby shops & restaurants, band c ...
From $271 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Chatham 3 Bedroom/2 Bath Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated and spacious 3 Bedroom 2 Full Bath Home on a private 1/2 acre setting in one of Chatham's sought a ...
From $307 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
South Chatham Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $305 per night (USD)
VRBO
From $1276 per night (USD)
Expedia
Charming Chatham Cottage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
...
From $1276 per night (USD)
Expedia
From $644 per night (USD)
VRBO
Cozy Cape near Chatham Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
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 qua ...
From $644 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Stylishly Furnished Home- Access to Pleasant Street Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*Cancellation policy at end of property description.* Sophisticatedly furnished and well maintained 3BR/2BA with a bon ...
From $675 per night (USD)
VRBO
Click For Pricing
VRBO
Pet friendly! Beautiful decor and great outdoor entertaining space for the whole family.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy your Chatham vacation at this spacious, newly furnished, 4 bedroom, 3 bath home. Offering 1 king, 2 queens, a bunk ...
Click For Pricing
VRBO
From $1767 per night (USD)
Expedia
Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!
Bedrooms:
6
Bathrooms:
6
Sleeps:
13
Experience your quintessential Cape Cod vacation in a beautifully renovated 1862 Farm House on Stage Harbor Road! Lush g ...
From $1767 per night (USD)
Expedia
From $592 per night (USD)
VRBO
Amazing Location! Lakefront Waterside Deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16629 - Dock Holiday: Amazing Location! Lakefront Waterside Deck The Space: Get ready for a week of rafting, c ...
From $592 per night (USD)
VRBO
From $345 per night (USD)
Expedia
15 Minute Walk to Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16632 - Casa Al Mare: 15 Minute Walk to Pleasant Street Beach! The Space: Your perfect seaside getaway starts ...
From $345 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Lucky Number Seven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $244 per night (USD)
VRBO
From $269 per night (USD)
Expedia
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE! CLOSE TO DOWNTOWN CHATHAM!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 ...
From $269 per night (USD)
Expedia
From $607 per night (USD)
VRBO
1 Mi to Beach: Home w/ Fire Pit & BBQ in Cape Cod!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2,688 Sq Ft | Dog Friendly w/ Fee | Wet Bar | Expansive Yard Nestled in the heart of South Chatham, this 3-bed, 2.5-bat ...
From $607 per night (USD)
VRBO
From $736 per night (USD)
Expedia
Walk to town, baseball games, Oyster Pond
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This well-maintained and updated 4 bedroom, 2 bath home is an excellent choice for your Chatham vacation. With two quee ...
From $736 per night (USD)
Expedia
From $792 per night (USD)
VRBO
Water View-Walk town/beach, pets considered, Linen Option
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
It's all about LOCATION-just steps from deeded access to the Mill Pond where you can launch your Kayak without ever havi ...
From $792 per night (USD)
VRBO
Click For Pricing
Expedia
Charming Chatham Home Close to Bassing Harbor!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Cancellation policy at end of property description.* Looking for the perfect home for your next Chatham vacation? Thi ...
Click For Pricing
Expedia
From $828 per night (USD)
VRBO
Water Views in Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
*Cancellation policy at end of property description.* Charming, perfect location and every amenity you could want! Th ...
From $828 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the heart of downtown Chatham, this gem offers an easy walk to dinner, ice cream, shopping, a movie, Oyster P ...
From $719 per night (USD)
Expedia
From $475 per night (USD)
VRBO
Waterfront on Private Lake!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: 16644 - Lover's Lookout: Waterfront on Private Lake! The Space: Enjoy your best days of summer at our waterfro ...
From $475 per night (USD)
VRBO
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Expedia
Charming home in downtown Chatham
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Main Street in Chatham! Spend your summer vacation relaxing on the front porch of this charming, quintessential Cape Cod ...
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Expedia
From $284 per night (USD)
VRBO
Location, Location, Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Comfortable, stylish Cape Cod home close to everything. Beach is .7 miles, Route 6 is 3 miles, Downtown is 1.5miles, Bik ...
From $284 per night (USD)
VRBO
From $675 per night (USD)
Expedia
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Welcome to The Chatham Carriage House, located within walking distance to Historic Main St. with it's endless vari ...
From $675 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Cozy Chatham home with privacy and nautical decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Retreat to the heart of Cape Cod in this restored Cape salt box cottage. Starry Hill Cottage combines elements of old Ca ...
From $454 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Game Room Walk to Nantucket Sound!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16606 - Chatham Charmer: Game Room Walk to Nantucket Sound! The Space: Nestled between Harwich Port and Chatha ...
From $459 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
After walking by the beautiful hydrangeas and entering through the front door you will realize this house is much more ...
From $587 per night (USD)
VRBO
From $772 per night (USD)
Expedia
Stellar Home with Hot Tub & Movie Room!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: 16614 - Chatham Pearl: Stellar Home with Hot Tub & Movie Room! The Space: Sitting in a quiet neighborhood in b ...
From $772 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Lovely Home Minutes from Beach in Chatham!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: 16605 - Sea Pine Cottage : Lovely Home Minutes from Beach in Chatham! The Space: This quaint Cape home is loca ...
From $280 per night (USD)
VRBO
From $636 per night (USD)
Expedia
Stunning Water Views 2 Decks! By Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16611 - Bucks Creek West: Stunning Water Views 2 Decks! By Beach! The Space: This comfortable family home sitt ...
From $636 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Quintessential Chatham Cottage by the Pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
If a true Cape Cod cottage is what you are looking for, your search ends here. Steps from Schoolhouse Pond, you can for ...
From $350 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Central AC Close to Beach Dog Friendly!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: 16613 - Maiden Chatham: Central AC Close to Beach Dog Friendly! The Space: Enjoy this beautifully renovated, w ...
From $315 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Walk to Ridgevale Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16612 - Salty Breeze: Walk to Ridgevale Beach! The Space: There is nothing like heading to Cape Cod and enjoyi ...
From $566 per night (USD)
VRBO
From $377 per night (USD)
Expedia
4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
My family and I live full time in Lexington, MA. We decided to purchase our first vacation home in Chatham, MA in 2008. ...
From $377 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Old Cape Cod Charm in Chatham MA, 1/4 mile Walking Distance to Hardings Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Quaint 3 bedroom 1 bath cottage, easy 1/4 mile walk to Hardings Beach, one of Chatham's best beaches on Nantucket sound. ...
From $289 per night (USD)
VRBO
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Expedia
Cozy Cockle Cove Retreat!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this adorable coastal cottage, perfectly nestled just half a mile from Cockle Cove Beach in Chatham. Offering ...
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Expedia
From $832 per night (USD)
VRBO
Beautifully Renovated w/ Access to Beach!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Summary: 16626 - Cape Whidah: Beautifully Renovated w/ Access to Beach! The Space: This gorgeous vacation home, located ...
From $832 per night (USD)
VRBO
From $102 per night (USD)
Expedia
Chatham Luxury! WALK to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Chatham Searenity! BEACH ACCESS! Walk to beautiful beach overlooking monomoy! 2 minutes from Chatham Bars Inn, Chatham l ...
From $102 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Great Location in Chatham Walk to town shop, dine, band concert, cape baseball
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Have a wonderful time on your Cape Cod vacation! Our home includes a new deck for your summer cookouts an outdoor shower ...
From $364 per night (USD)
VRBO
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Expedia
Sophisticated decor with an amazing use of space throughout this two bedroom (1 king and 2 twins) cottage.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming cottage, perfect for your next getaway. Its sophisticated decor and lovely wooden views create a serene and inv ...
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Expedia

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Results: 614 Rentals