Chatham Rentals
From $488 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 $488 per night (USD)VRBO
From $658 per night (USD)Expedia
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)Expedia
From $863 per night (USD)VRBO
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 $863 per night (USD)VRBO
From $243 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 $243 per night (USD)Expedia
From $632 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 $632 per night (USD)VRBO
From $471 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 $471 per night (USD)Expedia
From $313 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 $313 per night (USD)VRBO
From $333 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 $333 per night (USD)Expedia
From $547 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 $547 per night (USD)VRBO
From $651 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 $651 per night (USD)Expedia
From $322 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 $322 per night (USD)VRBO
From $504 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 $504 per night (USD)Expedia
From $809 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 $809 per night (USD)VRBO
From $669 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 $669 per night (USD)Expedia
From $789 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 $789 per night (USD)VRBO
From $511 per night (USD)Expedia
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 $511 per night (USD)Expedia
From $399 per night (USD)VRBO
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 $399 per night (USD)VRBO
From $1144 per night (USD)Expedia
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 ...
From $1144 per night (USD)Expedia
From $372 per night (USD)VRBO
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)VRBO
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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 ...
Click For PricingExpedia
From $2572 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 $2572 per night (USD)VRBO
From $587 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 $587 per night (USD)Expedia
From $552 per night (USD)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 ...
From $552 per night (USD)VRBO
From $1166 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 $1166 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
Click For PricingExpedia
Pet Friendly in Riverbay!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home for a family vacation! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay. There are 2 queens ...
Click For PricingExpedia
From $753 per night (USD)VRBO
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 $753 per night (USD)VRBO
From $318 per night (USD)Expedia
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 $318 per night (USD)Expedia
From $457 per night (USD)VRBO
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 $457 per night (USD)VRBO
From $556 per night (USD)Expedia
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 $556 per night (USD)Expedia
From $577 per night (USD)VRBO
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)VRBO
From $529 per night (USD)Expedia
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 $529 per night (USD)Expedia
From $537 per night (USD)VRBO
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 $537 per night (USD)VRBO
From $490 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 $490 per night (USD)VRBO
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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 ...
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From $846 per night (USD)Expedia
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 $846 per night (USD)Expedia
From $323 per night (USD)VRBO
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 $323 per night (USD)VRBO
From $733 per night (USD)Expedia
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 $733 per night (USD)Expedia
From $2594 per night (USD)VRBO
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 ...
From $2594 per night (USD)VRBO
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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 ...
Click For PricingExpedia
From $249 per night (USD)VRBO
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 $249 per night (USD)VRBO
From $274 per night (USD)Expedia
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 $274 per night (USD)Expedia
From $284 per night (USD)VRBO
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)VRBO
From $564 per night (USD)Expedia
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 $564 per night (USD)Expedia
From $404 per night (USD)VRBO
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 $404 per night (USD)VRBO
From $435 per night (USD)Expedia
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 $435 per night (USD)Expedia
From $296 per night (USD)VRBO
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 $296 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
From $358 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 $358 per night (USD)VRBO
From $315 per night (USD)Expedia
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)Expedia
From $887 per night (USD)VRBO
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 $887 per night (USD)VRBO
From $431 per night (USD)Expedia
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 $431 per night (USD)Expedia
From $578 per night (USD)VRBO
Walk to Beach-Water views-Central A/C and WiFi
- 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 $578 per night (USD)VRBO
From $858 per night (USD)Expedia
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 $858 per night (USD)Expedia
From $348 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 $348 per night (USD)VRBO
From $589 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 $589 per night (USD)Expedia
From $483 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 $483 per night (USD)VRBO
From $565 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 $565 per night (USD)Expedia
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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 ...
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From $1156 per night (USD)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 ...
From $1156 per night (USD)Expedia
From $1183 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 $1183 per night (USD)VRBO
From $360 per night (USD)Expedia
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 $360 per night (USD)Expedia
From $429 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 $429 per night (USD)VRBO
From $584 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 $584 per night (USD)Expedia
From $301 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 $301 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 $867 per night (USD)VRBO
From $662 per night (USD)Expedia
Air Conditioned, King bed Comfort .Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cranberry Cove, beautiful bright open-plan 3 bedroom house with central AC, a great room made for family time, with vaul ...
From $662 per night (USD)Expedia
From $517 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 $517 per night (USD)VRBO
From $660 per night (USD)VRBO
Stylishly Furnished Home- Access to Pleasant Street Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Cancellation policy at end of property description.* Sophisticatedly furnished and well maintained 3BR/2BA with a bon ...
From $660 per night (USD)VRBO
From $1268 per night (USD)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 ...
From $1268 per night (USD)VRBO
From $1408 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 $1408 per night (USD)Expedia
From $485 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 $485 per night (USD)VRBO
From $383 per night (USD)Expedia
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 $383 per night (USD)Expedia
From $306 per night (USD)VRBO
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 $306 per night (USD)VRBO
From $355 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 $355 per night (USD)Expedia
From $575 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 $575 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 $836 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 $836 per night (USD)VRBO
From $757 per night (USD)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 ...
From $757 per night (USD)Expedia
From $821 per night (USD)VRBO
Water Views in Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Cancellation policy at end of property description.* Charming, perfect location and every amenity you could want! Th ...
From $821 per night (USD)VRBO
From $656 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 $656 per night (USD)Expedia
From $394 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 $394 per night (USD)VRBO
From $1414 per night (USD)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 ...
From $1414 per night (USD)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 $452 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 $452 per night (USD)VRBO
From $559 per night (USD)Expedia
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 $559 per night (USD)Expedia
From $691 per night (USD)VRBO
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 $691 per night (USD)VRBO
From $298 per night (USD)Expedia
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 $298 per night (USD)Expedia
From $612 per night (USD)VRBO
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 $612 per night (USD)VRBO
From $386 per night (USD)Expedia
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 $386 per night (USD)Expedia
From $368 per night (USD)VRBO
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 $368 per night (USD)VRBO
From $345 per night (USD)Expedia
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 $345 per night (USD)Expedia
From $423 per night (USD)VRBO
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 $423 per night (USD)VRBO
From $431 per night (USD)Expedia
2-Story Home w/Gas Grill, Partial A/C, Deck, and W/D - near Bucks Creek Marshes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stevie, the Cape Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $431 per night (USD)Expedia
From $500 per night (USD)VRBO
Located on Rail Trail By Beach & Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16617 - Skipping Stone: Located on Rail Trail By Beach & Downtown! The Space: This beautifully updated home is ...
From $500 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
From $585 per night (USD)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 ...
From $585 per night (USD)Expedia