Chatham Rentals
From $844 per night (USD)VRBO
Waterfront, No Pet Fee, Fenced Yard, Close to Town and Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $844 per night (USD)VRBO
From $525 per night (USD)Expedia
0.6 Miles to Beach Great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you so ...
From $525 per night (USD)Expedia
From $598 per night (USD)VRBO
Game Room, Rooftop Deck, Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16678 - Jawsome Getaway: Game Room Rooftop Deck Fire Pit!! The Space: Chatham is the hub of entertainment ...
From $598 per night (USD)VRBO
From $242 per night (USD)Expedia
Charming Chatham Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidi ...
From $242 per night (USD)Expedia
From $591 per night (USD)VRBO
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $591 per night (USD)VRBO
From $509 per night (USD)Expedia
Gorgeous Home with Game Room Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation mea ...
From $509 per night (USD)Expedia
From $421 per night (USD)VRBO
Large Home w/ Fire Pit and Dogs Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where ba ...
From $421 per night (USD)VRBO
From $1165 per night (USD)Expedia
Beautiful and Pristine Rental in South Chatham.. Recently Reduced!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Awesome Three Bedroom Home on a Quiet Cul-de-sac in South Chatham! This beautiful home is perfect for your dream Chat ...
From $1165 per night (USD)Expedia
From $1024 per night (USD)VRBO
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful home located in the heart of Chatham! This lovely home offers all the amenities and decor of a modern house wh ...
From $1024 per night (USD)VRBO
From $1223 per night (USD)Expedia
Newly Refreshed Upscale Cottage/Pvt 2 KING BR Ensuite /1 Mile to Hardings Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oh Buoy Oh Buoy A Refined Chatham Retreat Escape to Oh Buoy Oh Buoy, a tastefully renovated Chatham cottage just one m ...
From $1223 per night (USD)Expedia
From $2291 per night (USD)VRBO
Pool and large yard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
We invite you to spend time with your family and enjoy all that Chatham has to offer at this beautiful North Chatham hom ...
From $2291 per night (USD)VRBO
From $648 per night (USD)Expedia
Walk to Beach: Chatham Gem w/ Ocean-View Sunroom!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bath ...
From $648 per night (USD)Expedia
From $647 per night (USD)VRBO
Classic Cape House Walking Distance to the Beach - Many recent upgrades
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Recent upgrades: Complete interior painted (March 2025); Main dining table refinished (April 2025); Downstairs bathroom ...
From $647 per night (USD)VRBO
From $1079 per night (USD)VRBO
Beautifully renovated home, outdoor space, pet considered
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $1079 per night (USD)VRBO
From $920 per night (USD)VRBO
Rail Trail Access: Home 2 Mi to Lighthouse Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $920 per night (USD)VRBO
From $1554 per night (USD)Expedia
Private and pet friendly with expansive back deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Private and pet friendly. The bright, open living and dining area features a large slider that leads directly to the bac ...
From $1554 per night (USD)Expedia
From $4793 per night (USD)VRBO
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound Rece ...
From $4793 per night (USD)VRBO
From $521 per night (USD)VRBO
Chatham EsCAPE: Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3-bedroom, 2-bathroom home is ideally situated between the tranquil Ridgevale Beach and the vibrant Chatha ...
From $521 per night (USD)VRBO
From $541 per night (USD)VRBO
Close to Beach Renovated Dog Friendly Cape Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
4 minutes from the beach and nestled on a spacious half acre set back more than 250 feet on a private road, this newly r ...
From $541 per night (USD)VRBO
From $809 per night (USD)Expedia
New! Chatham Cottage- 1 Mile to Downtown & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to our charming 2 bed/1 bath North Chatham cottage! A short walk to Chatham`s best beaches and downtown shops an ...
From $809 per night (USD)Expedia
Click For PricingVRBO
Steps to Chatham's Historic Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
Click For PricingVRBO
From $667 per night (USD)Expedia
Stroll To Lighthouse Beach or Chatham's Charming Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Best location to spend your days in Chatham! This comfortable condominium overlooks the peaceful marshland in the back a ...
From $667 per night (USD)Expedia
From $2017 per night (USD)VRBO
Great Location Steps to Chatham Lighthouse & Town
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRICE RECENTLY REDUCED BY $2500! Stunning four-bedroom home located in the heart of Chatham...tucked away in the Old ...
From $2017 per night (USD)VRBO
Click For PricingExpedia
Cozy cottage in delightful country side neighborhood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this cozy three-bedroom, two-bath cottage nestled in a peaceful countryside neighborhood. With central air, hi ...
Click For PricingExpedia
From $632 per night (USD)VRBO
Half Mile Walk to Beach, Dog Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 16691 - Seaside: Half Mile Walk to Beach, Dog Friendly! The Space: Located in the coveted Ridgevale Beach ...
From $632 per night (USD)VRBO
From $491 per night (USD)Expedia
Walk to Beach, Private Patio and Backyard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16690 - Chatham Haven: Walk to Beach, Private Patio and Backyard! The Space: Discover the charm of Chatham ...
From $491 per night (USD)Expedia
From $463 per night (USD)VRBO
Minutes to Red River Beach, Dog Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 17755 - Deer Run Hideaway: Minutes to Red River Beach, Dog Friendly! The Space: Welcome to Deer Run Hideaw ...
From $463 per night (USD)VRBO
Click For PricingExpedia
Saltaire: Coastal Getaway Near Hardings Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom - 2 Baths - Sleeps 6 During peak summer weeks, our properties typically require a 7-night stay, either Friday- ...
Click For PricingExpedia
From $11024 per night (USD)VRBO
Waterfront, Updated 4 Bedroom Home with Views of Stage Harbor & Nantucket Sound
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Recently updated waterfront home overlooking Snake River, Stage Harbor & Nantucket Sound on Stage Island. 4+ bedroom, 3 ...
From $11024 per night (USD)VRBO
From $753 per night (USD)VRBO
Walk to downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chatham adventure begins at this lovely 3-bedroom house. With 2 queen beds and 1 full bed, it's the perfect retreat ...
From $753 per night (USD)VRBO
From $1448 per night (USD)VRBO
Peaceful Patio near Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Great for two families and near Ridgevale Beach! This house is located in a quiet neighborhood on a cul-du-sac. A perf ...
From $1448 per night (USD)VRBO
From $830 per night (USD)VRBO
Cozy Chatham Getaway- minutes to all things Cape Cod!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect beach getaway in beautiful Chatham! This charming four-bedroom, two-bathroom cottage is just 2 m ...
From $830 per night (USD)VRBO
From $719 per night (USD)VRBO
Brand New Four Bedroom Home Near Beach and Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Brand new 4 bedroom, 2 bath North Chatham home near town and beach. On the first floor, the home boasts a designer kitch ...
From $719 per night (USD)VRBO
From $800 per night (USD)Expedia
Chatham Cape Cod Retreat, near boat yards, Harding's Beach, Stage Harbor Light
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This modern Chatham home, filled with books and art, and surrounded by nature, is a peaceful retreat for those who appre ...
From $800 per night (USD)Expedia
From $1069 per night (USD)VRBO
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stunning 4-Bedroom Oasis in a great location with Pool, Hot tub, and outdoor kitchen.. Your comfort and enjoyment are ...
From $1069 per night (USD)VRBO
From $723 per night (USD)Expedia
Sweeping Views, 150 Yards to Private Beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 16694 - Oceanside Delight: Sweeping Views, 150 Yards to Private Beach! The Space: Escape to Oceanside Deli ...
From $723 per night (USD)Expedia
From $348 per night (USD)VRBO
New listing! Cozy, fresh and clean 1-bedroom cottage with Pond access in Chatham
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy 1-bedroom cottage in Chatham is the perfect retreat for a couple’s or solo getaway. 2 occupants only please. S ...
From $348 per night (USD)VRBO
From $529 per night (USD)Expedia
Golf, Shop & Beach-Hop! Cape Cod Gem Steps to Sand
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Close to Golf Courses | 9 Mi to Nickerson State Park Discover where East Coast beaches meet small-town charm at this 2- ...
From $529 per night (USD)Expedia
From $409 per night (USD)VRBO
Walk to Water, near Downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16692 - Coastal Escape: Walk to Water, Near Downtown Chatham! The Space: Welcome to Coastal Escape, a char ...
From $409 per night (USD)VRBO
From $885 per night (USD)Expedia
The perfect cozy Chatham getaway awaits you!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your ideal Chatham getaway awaits in this cozy home, featuring 2 bedrooms, 1 bathroom, and within walking distance of do ...
From $885 per night (USD)Expedia
Click For PricingVRBO
Comfortable, Spacious North Chatham Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This fabulous second-floor condo is centrally located in Nickerson Corners in North Chatham, close to downtown and Light ...
Click For PricingVRBO
From $1596 per night (USD)VRBO
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Charming 5-Bedroom Home in the Heart of Downtown Chatham – Walk to Beach, Shops & More Welcome to your perfect Cape Cod ...
From $1596 per night (USD)VRBO
From $724 per night (USD)VRBO
Pet Friendly Waterfront Overlooking Oyster River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Special Off-Season Pricing Offered for Remaining In-Season June and July Weeks - Book and Save Breezes and Views ...
From $724 per night (USD)VRBO
From $1704 per night (USD)Expedia
All-New Coastal Luxury Near CBI & Beaches, Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, newly renovated home off Shore Rd. Steps to Chatham Bars Inn, Fish Pier, Cow Yard Beach, Veterans Field, and ...
From $1704 per night (USD)Expedia
From $488 per night (USD)VRBO
Quintessential Cape Cod Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
. Escape to our cozy Cape Cod cottage in Chatham! This charming, eclectic retreat is perfect for couples, solo adventure ...
From $488 per night (USD)VRBO
From $503 per night (USD)VRBO
The Nook on Nob Hill, The Nook on Nob Hill
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Walk to Downtown Chatham & Cape Cod Rail Trail The Perfect Cape Cod Vacation Rental for Families & Outdoor Enthusiast ...
From $503 per night (USD)VRBO
From $1107 per night (USD)VRBO
.5 miles to the Beach. Close to Wequasset. Foosball & Kid Friendly Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect for families, this cozy vacation home is packed with kid-friendly amenities! Enjoy a lovely deck, two spacious l ...
From $1107 per night (USD)VRBO
From $1283 per night (USD)VRBO
Pondside Retreat - Beach Access, Game Room, Firepit, Spacious Yard & Water Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect Cape Cod getaway for families or a group of friends! This beautiful retreat offers stunning pond ...
From $1283 per night (USD)VRBO
From $582 per night (USD)VRBO
Renovated Chatham Cottage – Steps to Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
The Space Newly renovated and ready for your best Cape Cod summer. This charming 3-bedroom, 1.5-bath home in South Chath ...
From $582 per night (USD)VRBO
From $1528 per night (USD)VRBO
Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Your family or group of friends will be close to everything when you stay at this centrally-located home. This cozy home ...
From $1528 per night (USD)VRBO
From $915 per night (USD)VRBO
Marsh and Nantucket Sound Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Booking Special - Reduced Rates for Remaining 2026 September Nights - Reduced from $800 to $500 per night (3 Night Min. ...
From $915 per night (USD)VRBO
From $3687 per night (USD)Expedia
Sophisticated Chatham Oasis with Pool & Spa RPAM062
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $3687 per night (USD)Expedia
From $1214 per night (USD)VRBO
Chatham Lovers Lake Waterfront Haven: Private Dock, 4BR/3BA & Lakeside Luxury
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the perfect blend of family adventure and serene “work-from-home” luxury at this stunning 3,154 sq. ft. Lovers ...
From $1214 per night (USD)VRBO
From $1127 per night (USD)VRBO
Luxurious Home with Pool & Game Room in Cape Cod
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to our newly listed vacation home in Chatham, Cape Cod! This spacious 4-bedroom/4.5-bathroom house is a haven fo ...
From $1127 per night (USD)VRBO
From $703 per night (USD)VRBO
Visit Cape Cod at a discount after summer! PM us about our 5 star Chatham home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This completely renovated and newly painted home is located on a private road and just a few minutes walk away from all ...
From $703 per night (USD)VRBO
From $1175 per night (USD)VRBO
Renovated Chatham Coastal Estate with Water Views and Room for Fourteen
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Fresh 2026 Renovations. Vintage Camp Vibes. Modern Coastal Luxury. Book now to secure your stay at Chatham Waterscape ...
From $1175 per night (USD)VRBO
From $2278 per night (USD)VRBO
The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
This property is professionally managed by Pretty Picky Properties Sleeps 16 Eight Bedrooms, Nine Baths Rents Friday to ...
From $2278 per night (USD)VRBO
From $579 per night (USD)Expedia
Direct Private Beach Access (2290)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offer ...
From $579 per night (USD)Expedia
From $2426 per night (USD)VRBO
Great Cockle Cove Home!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Family Retreat Destination! Let this 7 bedroom offering 2 queens, 4 twin, 2 full beds and 2 sets of bunk beds, spread o ...
From $2426 per night (USD)VRBO
From $789 per night (USD)VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 6
Fully renovated cottage on little mill pond. Renovation completed may 2016. A 4 minute walk to town of chatham. 3 bedroo ...
From $789 per night (USD)VRBO
From $1211 per night (USD)VRBO
The Barn at Chatham Oaks
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy ...
From $1211 per night (USD)VRBO
From $1037 per night (USD)VRBO
Renovated Cape Escape with Forest Beach in your backyard!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Wake up in our renovated home to fresh ocean views. Chatham’s Forest Beach is right in your backyard, where you can spen ...
From $1037 per night (USD)VRBO
From $2359 per night (USD)VRBO
Sophisticated Chatham Retreat with Private Pool and Spa RPAM093
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your private Chatham retreat, where modern luxury meets classic Cape Cod charm. This stunning four bedroom, f ...
From $2359 per night (USD)VRBO
From $759 per night (USD)VRBO
CHATHAM -WALK TO 3 SANDY BEACHES! OPEN Sept 1 -4, Sept 7 there after! RATE DROP!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
CHATHAM - WALK TO 3 BEAUTIFUL SANDY BEACHES ON NANTUCKET SOUND! FREE PARKING AT BOTH FOREST BEACH AND PLEASANT STREET B ...
From $759 per night (USD)VRBO
From $292 per night (USD)VRBO
Convenient to all amenities and beaches in Chatham
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Studio cottage with queen bed, full bath and kitchenette. Backyard area with brick patio/pergola and grill with an outd ...
From $292 per night (USD)VRBO
From $551 per night (USD)Expedia
Waterfront on Pond w/ Private Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 16664 - Family Tides: Waterfront on Pond w/ Private Beach! The Space: This beautiful waterfront property, ...
From $551 per night (USD)Expedia
From $412 per night (USD)VRBO
Lovely Home Near Bike Path Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16665 - Summer Breeze: Lovely Home Near Bike Path Dog Welcome! The Space: This lovely four bedroom vacatio ...
From $412 per night (USD)VRBO
From $1184 per night (USD)Expedia
Chatham Luxury Retreat—Porch, Art & Family Fun
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom - 3.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $1184 per night (USD)Expedia
From $575 per night (USD)VRBO
The Whistling Whale - Fantastic Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We're delighted to introduce "The Whistling Whale," a charming upstairs apartment over the garage offering a fantastic r ...
From $575 per night (USD)VRBO
From $749 per night (USD)Expedia
Charming House Close to Downtown-Pier-Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bdrm/2ba House -1 mile from Downtown- Close to Lighthouse Beach About our space Pack your bags and leave th ...
From $749 per night (USD)Expedia
From $422 per night (USD)VRBO
Chatham Beach Cottage + loft Walk to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the whole family at this year round Charming Chatham Seaside Cottage , with just a short 5 minute walk to a b ...
From $422 per night (USD)VRBO
From $1048 per night (USD)Expedia
Coastal Comfort & Cape Cod Charm Await
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
4 Bedroom - 2 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $1048 per night (USD)Expedia
From $1341 per night (USD)VRBO
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham! Experience beautiful water views with y ...
From $1341 per night (USD)VRBO
From $1497 per night (USD)Expedia
Located in a quiet neighborhood, less than a mile from downtown Chatham
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home is ideal for your family vacation! Located in a quiet neighborhood, it's less than a mile from downtown Chatha ...
From $1497 per night (USD)Expedia
From $588 per night (USD)VRBO
Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Newly built home, app 2900 sq feet, The 1st floor includes a master bedroom with private bath with tub/shower, king siz ...
From $588 per night (USD)VRBO
From $481 per night (USD)Expedia
1.2 miles from the beach & Private Bike Trail Access - Hillside Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this charming single-family home in South Harwich! Conveniently located off of Route 28, you’re only steps (5 ...
From $481 per night (USD)Expedia
From $523 per night (USD)VRBO
🐶 Dog Friendly Fenced in Yard! 3/2 🏠 1.1 mi to 🏝 WIFI - perfect fall rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Modern 3 bedroom, 2 full bath ranch style home located in Chatham! 1/10th of a mile to Old Colony Bike path and 1.1 mile ...
From $523 per night (USD)VRBO
From $1019 per night (USD)VRBO
Sweeping Water Views, Deeded Beach Access, Pet Friendly and AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Expansive 4 BD / 4 BA Property with AC, and sweeping views of Crows Pond The Space: This home is represent ...
From $1019 per night (USD)VRBO
Click For PricingVRBO
Walk to The Monomoy Wildlife Sanctuary. Great space for relaxing and entertaining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan your next vacation by the beach in this charming 3 bedroom, 2 bath home, which comfortably sleeps six with a double ...
Click For PricingVRBO
From $756 per night (USD)Expedia
Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc. Completely remodeled to perfectio ...
From $756 per night (USD)Expedia
Click For PricingVRBO
Beautiful 3 bedroom Cape with spacious deck and hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Lovely modern 3 bedroom home, located on a quiet cul-de-sac is the perfect place for a family vacation. Hop on the bike ...
Click For PricingVRBO
From $342 per night (USD)Expedia
Updated Beach House Deck Outdoor Shower!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! The Space: Nautical colors and floods of ...
From $342 per night (USD)Expedia
From $755 per night (USD)VRBO
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! It features ...
From $755 per night (USD)VRBO
From $1212 per night (USD)Expedia
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely place in South Chatham is our ne ...
From $1212 per night (USD)Expedia
Click For PricingVRBO
Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled ...
Click For PricingVRBO
From $660 per night (USD)VRBO
Star of the Sea - Newly Renovated Cape House .9Miles from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Escape to Star of the Sea a charming 2 story Cape house in South Chatham, MA. This delightful newly renovated rental fea ...
From $660 per night (USD)VRBO
From $658 per night (USD)VRBO
Cockle Cottage - Renovated Chatham Cape House .9 Miles from Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge in a memorable stay at Cockle Cottage in Chatham, MA. This inviting rental boasts 2 bedrooms, 1 bathroom and com ...
From $658 per night (USD)VRBO
From $1091 per night (USD)VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $1091 per night (USD)VRBO
From $557 per night (USD)VRBO
Cape Escape - Family-Friendly Chatham Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $557 per night (USD)VRBO
From $1651 per night (USD)Expedia
Upscale Elegance, Steps from Ridgevale Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your coffee overlooking Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed ...
From $1651 per night (USD)Expedia
From $572 per night (USD)VRBO
Walk to Main St and Oyster Pond in Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16685 - Slack Tide : Walk to Main St and Oyster Pond in Chatham! The Space: Discover the epitome of Cape C ...
From $572 per night (USD)VRBO
From $1771 per night (USD)Expedia
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
About this space Welcome to a beautiful Coastal retreat! — a spacious seaside escape perfect for families or groups. St ...
From $1771 per night (USD)Expedia
From $608 per night (USD)VRBO
Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...
From $608 per night (USD)VRBO
From $377 per night (USD)Expedia
1 Mi to Sand! Mid-Cape Chatham w/ Furnished Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps f ...
From $377 per night (USD)Expedia
From $658 per night (USD)VRBO
Roof Deck, Walk to Forest Beach, Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit! The Space: Inn Bloom is perched on a small h ...
From $658 per night (USD)VRBO
From $745 per night (USD)Expedia
Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly! ...
From $745 per night (USD)Expedia
From $467 per night (USD)VRBO
Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly! The Space: In this Quin ...
From $467 per night (USD)VRBO
From $373 per night (USD)Expedia
Movie Theater Room, Direct Access to Bike Trail!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: 16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail! The Space: Escape to this charming Cha ...
From $373 per night (USD)Expedia
From $3860 per night (USD)VRBO
Lovely home with heated pool, dock and the best views! RPMS158
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Michelle Sylvia coastal collection. Nestled on its own exclusive point within the private Stage Island enclave, this s ...
From $3860 per night (USD)VRBO
From $357 per night (USD)Expedia
Charming 2 bedroom condo on Private Beach by Outer Most Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Get ready to relax in this 2-bedroom townhome in Chatham. This awesome property features 2 queen beds and 1 twin bed, pe ...
From $357 per night (USD)Expedia