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From $561 per night (USD)
VRBO
Chatham Preservation Award: Antique Cape in Chatham Center
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
2010 Chatham Preservation Award Recipient This 1820 Cape was completely restored in 2008 and combines a classic exterio ...
From $561 per night (USD)
VRBO
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Expedia
Unique family gathering place ,Bright, Spacious. Linens included
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This home is perfect for a large family gathering. The home is situated on a large , quiet lot south of Route 28. Gues ...
Click For Pricing
Expedia
$5 Bed\/2 Bath Sleeps 11. Walk to restaurants, town and more...$
From $877 per night (USD)
VRBO
5 Bed\/2 Bath Sleeps 11. Walk to restaurants, town and more...
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Located just 1 mile from the fish pier and CBI, and 1.5 miles to downtown, we are close to all the best Chatham has to o ...
From $877 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Chatham Escape!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
South Chatham Cottage at the end of quiet street. Walk 1/2 mile to Pleasant Street Beach-Nantucket Sound. Quick access ...
From $282 per night (USD)
VRBO
From $612 per night (USD)
VRBO
STYLISH CHATHAM HOUSE
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located within walking distance to a small beach and quick drive to the local shops and restaurants of Main Street i ...
From $612 per night (USD)
VRBO
From $1106 per night (USD)
VRBO
Cozy Family Home in Chatham - Firepit, Game Room, Large Deck, Yard + More
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
This lovely home is the perfect getaway for families or a group of friends looking for a home filled with entertainment ...
From $1106 per night (USD)
VRBO
$\Cape Escape\ Sunny Renovated House - Walk To Beach, Pickleball, Central AC$
From $601 per night (USD)
VRBO
\"Cape Escape\" Sunny Renovated House - Walk To Beach, Pickleball, Central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Walking Distance to the beach! Updated home with indoor/outdoor living and separate living room and family room both wit ...
From $601 per night (USD)
VRBO
From $1240 per night (USD)
VRBO
Waterfront house on Cape Cod in Chatham, MA.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Enjoy the peaceful tranquility of our beachfront house on Cape Cod in Chatham, Massachusetts. Experience picturesque oce ...
From $1240 per night (USD)
VRBO
From $913 per night (USD)
VRBO
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
Located overlooking Chatham's beautiful Oyster Pond, this home is the perfect location for your vacation. Take advantage ...
From $913 per night (USD)
VRBO
From $645 per night (USD)
VRBO
Sandcastle By the Beach - 300 yards to Ridgevale Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Recently renovated, beautifully appointed, adorable 3 bedroom, 1.5 bath home that is literally a 3 minute walk to Ridgev ...
From $645 per night (USD)
VRBO
From $573 per night (USD)
VRBO
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
This charming and totally renovated (see updated pictures below) Chatham home is on a private road in a downtown neighbo ...
From $573 per night (USD)
VRBO
From $538 per night (USD)
VRBO
In Town Newly Renovated Cape
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Location, Location, Location – New to the rental market, this fully renovated centrally located cape home checks all the ...
From $538 per night (USD)
VRBO
From $293 per night (USD)
VRBO
Quaint Two Bedroom Lakeside Cottage #18 with Screened-in Porch in Chatham
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Must bring your own linens. New kitchen, granite counter tops, new hardwood floors, new drywall and paint. Cathedral c ...
From $293 per night (USD)
VRBO
From $830 per night (USD)
VRBO
New Waterfront Townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $830 per night (USD)
VRBO
From $548 per night (USD)
VRBO
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Right down the hill from the famous Chatham Light House, this one-floor living, 2 bedroom, 2 full bath end-unit condo is ...
From $548 per night (USD)
VRBO
$Stroll Chatham's Historic Downtown \/ Shops, Dining, Galleries, Etc.$
From $770 per night (USD)
Expedia
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 $770 per night (USD)
Expedia
From $938 per night (USD)
VRBO
THE CHATHAM TREEHOUSE 7 minutes from the Village
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to the Treehouse, just 7 mins from the village of Chatham! This beautiful, private property is nestled in the wo ...
From $938 per night (USD)
VRBO
From $1043 per night (USD)
Expedia
Charming and cozy, and right off the Chatham Loop!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the charm and coziness of Cedar Street, a highly desirable location just off the Chatham Loop! This vacation re ...
From $1043 per night (USD)
Expedia
From $822 per night (USD)
VRBO
Beautiful and Pristine Rental in South Chatham.. Recently Reduced!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Awesome Three Bedroom Home on a Quiet Cul-de-sac in South Chatham! This beautiful home is perfect for your dream Chath ...
From $822 per night (USD)
VRBO
From $773 per night (USD)
VRBO
Beautiful Chatham home...3 minute walk to salt water ocean beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Great location, spacious home and yard, private deck with brand new gas grill and comfy furniture. Beautifully decorated ...
From $773 per night (USD)
VRBO
From $277 per night (USD)
VRBO
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 $277 per night (USD)
VRBO
From $659 per night (USD)
Expedia
WATERFRONT home close to Downtown Chatham!
Bedrooms:
4
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 $659 per night (USD)
Expedia
From $564 per night (USD)
VRBO
0.6 Miles to Beach Great for families!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you soak u ...
From $564 per night (USD)
VRBO
From $600 per night (USD)
Expedia
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 and ...
From $600 per night (USD)
Expedia
Click For Pricing
VRBO
The Great Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private setting on quiet street on the outskirts of Chatham. Walk to beaches, bike path, local restaurants, short drive ...
Click For Pricing
VRBO
From $442 per night (USD)
Expedia
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated year round 4 bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $442 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Friendly retreat with a deck, AC, and board games - stellar central location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Corner Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $372 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Vacation in the heart of Chatham and walk to everything. Oyster Pond Beach is right around the corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience downtown Chatham! No need to drive when you can walk to everything. This charming rental features a classic f ...
From $758 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $530 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $363 per night (USD)
Expedia
From $531 per night (USD)
VRBO
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 means a ...
From $531 per night (USD)
VRBO
Click For Pricing
Expedia
Chatham Ocean View Home, Beach Accesso, 3 Decks, Pets Considered, Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our beautiful Cape Cod beach house is perfect for a relaxing vacation with family or friends. Nantucket Sound views and ...
Click For Pricing
Expedia
$Large Home w\/ Fire Pit and Dogs Welcome!$
From $389 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 baysid ...
From $389 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Cozy Chatham Getaway- minutes to all things Cape Cod- New listing!
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 $575 per night (USD)
Expedia
From $571 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. The property boasts a designer kitchen, luxury marbl ...
From $571 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Chatham Cape Cod Retreat, near boat yards, Harding's Beach, Stage Harbor Light
Bedrooms:
3
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 $744 per night (USD)
Expedia
From $1120 per night (USD)
VRBO
Private Beach, Beautiful Neighborhood, Well-Behaved Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
The perfect spot, offering lovely outdoor amenities such as a large, beautiful hedged yard for outdoor activities, a cov ...
From $1120 per night (USD)
VRBO
From $643 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 $643 per night (USD)
VRBO
From $711 per night (USD)
VRBO
Walk to Hardings Beach and private association beach, newly refreshed
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- ...
From $711 per night (USD)
VRBO
From $589 per night (USD)
Expedia
3-bedroom house in charming Chatham with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
From $589 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Quiet South Chatham 2-Bedroom House, Close To Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Just listed well kept 2 bedroom Chatham home just a short drive from popular Rigdevale, Cockle Cove, and Hardings beache ...
From $399 per night (USD)
VRBO
From $1488 per night (USD)
Expedia
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 $1488 per night (USD)
Expedia
Click For Pricing
VRBO
Amazing 4 Bedroom Home! Walk to Downtown Chatham and Oyster Pond!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Beautiful four bedroom home located just steps to all the signature shops and restaurants on Main Street! Leave your str ...
Click For Pricing
VRBO
From $411 per night (USD)
Expedia
Cozy Retreat in South Chatham (2374)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our cozy single-family home located in beautiful South Chatham. This property features 3 comfortable bedrooms ...
From $411 per night (USD)
Expedia
From $473 per night (USD)
VRBO
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 ...
From $473 per night (USD)
VRBO
From $951 per night (USD)
Expedia
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Stunning 4-Bedroom Oasis in a great location with Pool, Hot tub, and outdoor kitchen.. Your comfort and enjoyment are ...
From $951 per night (USD)
Expedia
From $365 per night (USD)
VRBO
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Bedrooms:
1
Bathrooms:
3
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 $365 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Charming Chatham Abode with Sunroom!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16686 - Chatham Life: Charming Chatham Abode with Sunroom! The Space: Embark on a journey into the quintessent ...
From $444 per night (USD)
Expedia
From $1002 per night (USD)
VRBO
Pet friendly home with beautiful views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Pet Friendly with beautiful views!! Bright open living, dining area has a large slider right onto the back deck with wat ...
From $1002 per night (USD)
VRBO
$Stroll to Chatham's Popular Shops & Dining \/ Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound$
From $3929 per night (USD)
Expedia
Stroll to Chatham's Popular Shops & Dining \/ Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound . Recent ...
From $3929 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Newly Renovated Home in Chatham, Walk to Town and Beach: 016-C
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties. Newly Renovated Home in Chatham, Walk to Town and B ...
From $709 per night (USD)
VRBO
From $485 per night (USD)
VRBO
Chatham EsCAPE: At The Heart Of It All!
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 $485 per night (USD)
VRBO
From $425 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 $425 per night (USD)
VRBO
Click For Pricing
Expedia
Steps to Chatham's Historic Downtown
Bedrooms:
3
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 Pricing
Expedia
From $602 per night (USD)
VRBO
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 ...
From $602 per night (USD)
VRBO
From $2091 per night (USD)
Expedia
Beautiful 5 BR property with pool and hot tub!
Bedrooms:
5
Bathrooms:
3
Sleeps:
10
2024 Rental Rates: In-Season: $11,000 per week, Plus Fees and Taxes No Off-Season Click for More Photos, Map, and A ...
From $2091 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Fantastically located Chatham house - New patio, refurbished
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Fantastically located Chatham house - New patio, refurbished ( PET FRIENDLY) Beautiful Family Home w/ fire pit and <1 ...
From $625 per night (USD)
VRBO
From $560 per night (USD)
Expedia
Stroll To Lighthouse Beach or Chatham's Charming Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
NEW LOWER PRICING! Best location to spend your days in Chatham! This comfortable condominium overlooks the peaceful m ...
From $560 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Waterfront Pet Friendly Home, with best views in Chatham!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Classic, Cape Cod home, sitting high above Oyster River and Stage Harbor Lighthouse... Views from every window! Plenty ...
From $1122 per night (USD)
VRBO
From $892 per night (USD)
VRBO
Beautifully renovated home, outdoor space, pet considered
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Sea~a~Bella - Your perfect Chatham family vacation is here. You will find three beautiful, scenic beaches within walking ...
From $892 per night (USD)
VRBO
From $395 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 $395 per night (USD)
VRBO
$Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!$
From $415 per night (USD)
Expedia
Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $415 per night (USD)
Expedia
$Newly Renovated Upscale Cottage\/Pvt 2 KING BR Ensuite \/1 Mile to Hardings Beach$
From $467 per night (USD)
VRBO
Newly Renovated Upscale Cottage\/Pvt 2 KING BR Ensuite \/1 Mile to Hardings Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oh Buoy Oh Buoy Escape to Oh Buoy Oh Buoy, our tastefully renovated Chatham cottage just one mile from the soft, white ...
From $467 per night (USD)
VRBO
Click For Pricing
Expedia
Downtown Chatham 4 Bedroom House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom house at end of private, dead-end street in Downtown Chatham. 2 decks, views of conservation land. Listen to ...
Click For Pricing
Expedia
From $382 per night (USD)
VRBO
Bright home walking distance to Main Street with great patio, firepit & bikes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Queen Anne Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $382 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Inviting apartment with patio, full kitchen, & golf nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Reynard's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $274 per night (USD)
Expedia
$Chatham Getaway w\/ Sunroom: Walk to Beach!$
From $497 per night (USD)
VRBO
Chatham Getaway w\/ Sunroom: Walk to Beach!
Bedrooms:
2
Bathrooms:
5
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 $497 per night (USD)
VRBO
From $1766 per night (USD)
Expedia
Pool and large yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
North Chatham home with a large yard and a lovely pool. The large front room is perfect for reading or watching TV, pla ...
From $1766 per night (USD)
Expedia
Click For Pricing
VRBO
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Chatham Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For Pricing
VRBO
From $459 per night (USD)
Expedia
Cozy Chatham Cottage walk to Hardings ⛱️ , Restaurants & downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly remodeled 1950's era cottage with all the comforts for a great visit. Just off the living room and thru French do ...
From $459 per night (USD)
Expedia
From $960 per night (USD)
VRBO
Malabar: 407-CB Chatham Charm, Walk to Beach and Town
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Chatham Charm, Walk to Beach and Town NEW Listing ...
From $960 per night (USD)
VRBO
From $895 per night (USD)
Expedia
Cape Escape: 048-CS Luxurious Chatham Home with Expansive Water Views
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views N ...
From $895 per night (USD)
Expedia
From $1356 per night (USD)
VRBO
Chatterbox: 032-CB Chatham Charm in the Heart of Town
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Chatham Charm in the Heart of Town NEW Listing for ...
From $1356 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Bright cape cod retreat; steps to White pond, bike path, CAC & fire pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunny-Side Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $300 per night (USD)
Expedia
Click For Pricing
VRBO
Great Location Steps to Chatham Lighthouse & Town
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Stunning four-bedroom home located in the heart of Chatham...tucked away in the Old Village section of town, you can w ...
Click For Pricing
VRBO
From $424 per night (USD)
Expedia
Half Mile Walk to Beach, Dog Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16691 - Seaside: Half Mile Walk to Beach, Dog Friendly! The Space: Located in the coveted Ridgevale Beach area ...
From $424 per night (USD)
Expedia
From $477 per night (USD)
VRBO
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 at ...
From $477 per night (USD)
VRBO
From $319 per night (USD)
Expedia
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 Hideaway, ...
From $319 per night (USD)
Expedia
$Spacious home located steps to the beach with patio, W\/D, AC, & kayaks$
From $427 per night (USD)
VRBO
Spacious home located steps to the beach with patio, W\/D, AC, & kayaks
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Crows Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $427 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Walk to Beach: South Chatham Home
Bedrooms:
1
Bathrooms:
3
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 $346 per night (USD)
Expedia
From $434 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 charming ...
From $434 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Charming antique cottage walk to everything downtown Chatham !
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your cozy getaway awaits in Chatham at this adorable Main Stret in town antique cottage ! One block walk to the Squire ...
From $246 per night (USD)
Expedia
From $668 per night (USD)
VRBO
Close to Ridgevale Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Short walk to Ridgevale Beach! This 3 bedroom house (king, 4 twins) and 2 full baths allows plenty of space for the enti ...
From $668 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Close to Forest Beach!!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Spacious Farmer's Porch and close to Forest Beach!! Cozy 4BR (Queen, King, 4 Twins) 1.5 Bath in South Chatham! Grab the ...
From $479 per night (USD)
Expedia
From $558 per night (USD)
VRBO
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 $558 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Fantastic Main Street location!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Fantastic Location!! This charming one-bedroom studio, upstairs apartment with a queen bed and futon is light, bright, a ...
From $385 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Peaceful and private retreat in West Chatham.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Create unforgettable memories with your loved ones at this peaceful and private retreat in West Chatham. This spacious t ...
From $536 per night (USD)
VRBO
From $1530 per night (USD)
Expedia
Vintage 1730 Farmhouse
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This vintage farm style home built in 1730 has 4 bedrooms (3 kings, 1 queen) and 4 bathrooms and a den that has a trundl ...
From $1530 per night (USD)
Expedia
From $278 per night (USD)
VRBO
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 ...
From $278 per night (USD)
VRBO
From $744 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 Delight, ...
From $744 per night (USD)
Expedia
From $1001 per night (USD)
VRBO
Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool ...
From $1001 per night (USD)
VRBO
From $259 per night (USD)
Expedia
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 $259 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Quintessential Cape Cod Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
My cottage is close to Harding's & Ridgevale beach, Chatham farmer market, convenience stores, restaurants and sandwich ...
From $344 per night (USD)
VRBO
From $591 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 Enthusiasts ...
From $591 per night (USD)
VRBO
From $1250 per night (USD)
VRBO
Pondside Retreat - Beach Access, Game Room, Firepit, Spacious Yard & Water Views
Bedrooms:
4
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 $1250 per night (USD)
VRBO
From $989 per night (USD)
VRBO
Spacious 4-bedroom house in Chatham - Walkable to Oyster Bay Pond & Downtown.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Enjoy the wonders of Chatham in our family's summer home. Located a 2 minute walk from Oyster Bay Pond and 8 minutes fr ...
From $989 per night (USD)
VRBO
From $953 per night (USD)
VRBO
Family Friendly Home. Kid Amenities. Beach Nearby!
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 $953 per night (USD)
VRBO
From $1089 per night (USD)
VRBO
Downtown Chatham Family Retreat - Spacious Deck, Games & Firepit - Walk to town
Bedrooms:
3
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 $1089 per night (USD)
VRBO
From $783 per night (USD)
VRBO
Marsh and Nantucket Sound Views!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
PETS ALLOWED WITH OWNER APPROVAL If you love the beach, views of the water and a beautiful home with every amenity, ...
From $783 per night (USD)
VRBO
From $3490 per night (USD)
Expedia
Sophisticated Chatham Oasis with Pool & Spa RPAM062
Bedrooms:
9
Bathrooms:
6
Sleeps:
12
Welcome to 84 Doane Road in Chatham, MA, where opulence meets comfort and convenience. Nestled in a prime location just ...
From $3490 per night (USD)
Expedia

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