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From $707 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 $707 per night (USD)
VRBO
From $258 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 $258 per night (USD)
Expedia
From $384 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 $384 per night (USD)
VRBO
From $613 per night (USD)
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 ...
From $613 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Sun Room Beaches and Dog Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16649 - Sunny Skies: Sun Room Beaches and Dog Welcome! The Space: From your doorstep, take a stroll, bike ride ...
From $271 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Great Chatham Location w/ Hot Tub, Near Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: 16650 - The Beach Buoys: Great Chatham Location w/ Hot Tub, Near Beach! The Space: Access to beaches, a quinte ...
From $455 per night (USD)
Expedia
From $471 per night (USD)
VRBO
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Absolutely beautiful vacation home with upscale furnishings throughout! Giant wraparound porch complete with comfy furni ...
From $471 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Hot Tub, Fenced Yard & Dog Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: 16651 - Smooth Sailing: Hot Tub, Fenced Yard & Dog Friendly The Space: Keep it classy this summer and spend a ...
From $759 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Fully Updated Home w/ Great Outdoor Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16648 - Quail Trail: Fully Updated Home w/ Great Outdoor Space! The Space: This beautifully updated house in S ...
From $218 per night (USD)
VRBO
From $687 per night (USD)
VRBO
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to The Salty Breeze! Come enjoy the perfect vacation spent in Chatham, one of the most desirable summertime dest ...
From $687 per night (USD)
VRBO
From $473 per night (USD)
VRBO
Spacious w/ Large Outdoor Area Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit! The Space: Our beautifully decorated, spacious ...
From $473 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Great Location Outdoor Space Dog Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: 16601 - The Salty Seashell: Great Location Outdoor Space Dog Friendly The Space: Wide planked Pine Hardwood fl ...
From $475 per night (USD)
Expedia
From $411 per night (USD)
VRBO
Chatham Village - Center - Main Street Center Area
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This is a fantastic - location right off main street in Chatham downtown area - 5 minute walk to Oyster Pond Ocean Inlet ...
From $411 per night (USD)
VRBO
From $225 per night (USD)
Expedia
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cottage is an affordable Chatham getaway destination for a couple or small family who want to experience Cape Cod. ...
From $225 per night (USD)
Expedia
From $544 per night (USD)
VRBO
Charming Walk to Beach Chatham-Bayview Cottage 3 BR--Central A/C; Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Every room in this year-round home has been totally renovated and redesigned just a few years ago. The Living Room ha ...
From $544 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sea House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $274 per night (USD)
Expedia
From $593 per night (USD)
VRBO
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
STEPS FROM OYSTER POND, SHORT WALK TO TOWN AND CAPE LEAGUE BASEBALL GAMES! This truly is a unique beach house in an excl ...
From $593 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Beautifully Renovated Cape on Bike Trail, 1 mile to Downtown Chatham and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Charming Cape house recently renovated less than a mile to Downtown Chatham for shopping and restaurants. Located on a q ...
From $270 per night (USD)
VRBO
From $648 per night (USD)
VRBO
Walk to Downtown Chatham, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 16688: Sand Bar - Walk to Downtown Chatham, Steps to Beach! The Space: Introducing Sand Bar: Your Private Have ...
From $648 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Waterfront Home With Dock and Two Water Facing Decks! (2372)
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of ...
From $525 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Beach Bag Ready & Friday to Friday Rental!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
FRIDAY TO FRIDAY RENTAL.... Cozy beach house sleeps 9 with 4 bedrooms (2 queen, double, 2 twins) and 2 baths, hardwood f ...
From $445 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Water-view house near golf with firepit, grill, deck, central AC & washer/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $421 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Stunning Marsh Views, Near Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16689: Lady Slipper - Stunning Marsh Views, Near Pleasant St. Beach! The Space: Nestled in the serene enclave ...
From $567 per night (USD)
VRBO
From $1043 per night (USD)
Expedia
3 Bedroom Sea-Side Cottage w/ Beach Access RPAM083
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled at the end of Little Beach Road in Chatham, this charming 3-bedroom, 2-bathroom cottage invites you to indulge i ...
From $1043 per night (USD)
Expedia
From $778 per night (USD)
VRBO
2 Bedroom Sea-Side Cottage w/ Beach Access RPAM085
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled at the end of Little Beach Road in Chatham, this charming 2-bedroom, 1-bathroom cottage invites you to indulge i ...
From $778 per night (USD)
VRBO
From $417 per night (USD)
Expedia
Charming house with patio, Washer/Dryer, & central location
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Dreamcatcher Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $417 per night (USD)
Expedia
From $1117 per night (USD)
VRBO
New Home, Dogs ok. A/C, near beach, shopping
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 $1117 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Wifi, AC, 4 bedrooms, 3 bathrooms, additional sleep space and bonus living room in the lower level
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $531 per night (USD)
Expedia
From $751 per night (USD)
VRBO
Luxury Waterfront with Game Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 16693 - Chatham Homecoming: Luxury Waterfront with Game Room! The Space: Perched above the shimmering waters o ...
From $751 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Elbow Inn: Private Retreat with Two Master Suites
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This spacious Chatham beach house comfortably sleeps 8, making it the perfect retreat for families or friends. With 4 be ...
From $642 per night (USD)
Expedia
From $2719 per night (USD)
VRBO
Beautiful sunsets and saltwater views from every room
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Magnificent, wraparound saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to ...
From $2719 per night (USD)
VRBO
From $504 per night (USD)
VRBO
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Book your Cape Cod escape where location, historic charm, and value unite! Our beautifully preserved and updated 1930s h ...
From $504 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Oar'asis: 093-C Charming Newly Renovated Retreat in Chatham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Charming Newly Renovated Retreat in Chatham NEW Li ...
From $586 per night (USD)
VRBO
From $976 per night (USD)
Expedia
Unique Private Chatham Getaway with Lap Pool & Deck Lounge (2403)
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect Chatham retreat—new to the rental market and truly one-of-a-kind. Built right into a hillside, t ...
From $976 per night (USD)
Expedia
From $1635 per night (USD)
VRBO
Coastal Retreat Minutes from Hardings Beach!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Coastal retreat in West Chatham - Minutes from Hardings Beach! Escape to this stunning, recently renovated beach house n ...
From $1635 per night (USD)
VRBO
From $511 per night (USD)
Expedia
Chatham Vineyard View
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this cozy three-bedroom, two-bath cottage nestled on a private cul-de-sac. A bright and sunny sunroom adds ter ...
From $511 per night (USD)
Expedia
From $1218 per night (USD)
VRBO
Spacious 7-bedroom house with WiFi, AC in charming Chatham
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Beautifully decorated family compound features Cottage with 2 bedrooms (1 K, 1 Q) + Loft (4 twin beds), and four (4) "bo ...
From $1218 per night (USD)
VRBO
Click For Pricing
VRBO
Walk to town and beach from this updated 3BR house in historic Chatham
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Recently renovated for 2025 to include updated bathrooms and new furnishings. NEW photos coming soon! A fantastic, famil ...
Click For Pricing
VRBO
From $715 per night (USD)
VRBO
Pleasant Street Hideaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to the beauty of Cape Cod in this cozy 3-bedroom, 3-bathroom cottage, just a short stroll from Pleasant Street Be ...
From $715 per night (USD)
VRBO
Click For Pricing
Expedia
Bright, dog-friendly property located close to Jackknife Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This bright, dog-friendly rental features a fenced yard and is conveniently located near Jacknife Beach. The property in ...
Click For Pricing
Expedia
From $551 per night (USD)
VRBO
Cape Cod Beach Getaway walk to the beach Relax in Coastal Comfort
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedrooms- 2.5 Bathrooms- Sleeps 8 During peak summer weeks, it is typical for our properties to require a 7-night stay ...
From $551 per night (USD)
VRBO
From $753 per night (USD)
Expedia
3-bedroom house in charming North Chatham with AC, WiFi. Enjoyable getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Live like a local in North Chatham at this charming 3-bedroom retreat. Each bedroom features a queen bed, designed for r ...
From $753 per night (USD)
Expedia
From $1119 per night (USD)
VRBO
Charming 4-bedroom house with fresh water dock & shark-free swimming!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this enchanting house in Chatham. This phenomenal home has been completely renovated over the past few years ...
From $1119 per night (USD)
VRBO
From $598 per night (USD)
Expedia
Mooncusser Cottage on Taylor's Pond!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Mooncusser! Fabulous two bedroom (1 king, 2 doubles) with a den (sleep sofa) waterfront cottage on saltwater ...
From $598 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Private Beach, Water Views, Incredible Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16695 - Tide's Edge: Private Beach, Water Views, Incredible Location! The Space: Welcome to Tide's Edge, a ser ...
From $596 per night (USD)
VRBO
From $820 per night (USD)
VRBO
Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to this delightful cottage nestled in picturesque Chatham—your perfect home base for Cape adventures! With 3 comf ...
From $820 per night (USD)
VRBO
From $1306 per night (USD)
VRBO
Spacious Lakefront Escape - Perfect for Families
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Welcome to our spacious lakefront home, perfect for families and large groups! With two master suites, four additional b ...
From $1306 per night (USD)
VRBO
From $829 per night (USD)
VRBO
Soundside Sanctuary - Chatham Home Close to Forest Beach & The Rail Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Soundside Sanctuary! Nestled in a quiet Chatham neighborhood, this peaceful retreat offers spacious, updated ...
From $829 per night (USD)
VRBO
From $925 per night (USD)
VRBO
NEW! Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $925 per night (USD)
VRBO
From $702 per night (USD)
VRBO
4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in Chatham, this charming house offers 4 bedrooms - 2 queen beds, 1 full bed, and 1 twin bed. With 2.5 bathrooms ...
From $702 per night (USD)
VRBO
From $624 per night (USD)
VRBO
3BR - Large Fenced In Yard, Patio, Near Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location: Located on a dead-end road near the head of Pleasant Bay. This 3 bedroom home offers a large fenced in yard wi ...
From $624 per night (USD)
VRBO
From $681 per night (USD)
VRBO
Downtown Chatham Luxurious & Spacious Condo w/ Roof Deck - Close to Oyster Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is ...
From $681 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Beautiful Chatham, Sun Sand & Surf. 8/10 mile to beaches ,pet friendly home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Island view is a beautiful Chatham beach house Located in a quite cul- de- sac , think about the warm tranquil mornings ...
From $521 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on ...
From $378 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. ...
From $547 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Beautiful Retreat / Hot tub/ Walk to Ridgevale Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Lovely, sun-filled, completely renovated, 4 bedroom 2 full bath house located within walking distance to beautiful, kid- ...
From $423 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Short Walk to Beach From Clean, Beautiful 3BR/2BA Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pretty, completely renovated 3BR home on quiet cul de sac, located w/in a 5-10 minute stroll to beautiful, family-friend ...
From $426 per night (USD)
VRBO
From $434 per night (USD)
VRBO
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Check in to this beautifully renovated West Chatham ranch, located south of 28 on a quiet cul-de-sac perfect for familie ...
From $434 per night (USD)
VRBO
From $622 per night (USD)
VRBO
Near Beach, bike trail, Central AC, WiFi, Private Neighborhood
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 Bedroom- 3 Bathroom- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $622 per night (USD)
VRBO
From $456 per night (USD)
VRBO
Stunning Water Views, Swim and Kayak in Tidal River, Walk to Beach, AC, Like New
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The River House is a recently built, beautifully furnished home, with stunning views of an idyllic bird watcher’s tidal ...
From $456 per night (USD)
VRBO
From $507 per night (USD)
VRBO
Charming/Great Location/Walk to town/baseball field
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfect location. Minute walk to town, baseball field, fish pier and beach. Bike path is right down the street. This ...
From $507 per night (USD)
VRBO
From $949 per night (USD)
Expedia
Enjoy your own private pool in Chatham! (2252)
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This uniquely beautiful home located in historic Chatham comfortably sleeps 10 with 5 sleeping spaces, 2.5 baths, plus t ...
From $949 per night (USD)
Expedia
From $564 per night (USD)
VRBO
Charming Chatham condo - Oyster Pond views, pool, tennis court and water access
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy the Chatham breezes and take advantage of the best the Cape has to offer whether staying on the property or g ...
From $564 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Hidden Gem - Captain's Haven
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest loc ...
From $199 per night (USD)
VRBO
From $782 per night (USD)
VRBO
22 Veterans’ Field Rd., Chatham, MA: Home Plate
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Description: *Four bedrooms (plus outbuilding with daybeds sleeping four and heating/cooling…great for teens!) *Beds for ...
From $782 per night (USD)
VRBO
From $766 per night (USD)
VRBO
New July dates! Sun drenched Cape haven- spectacular deck, garden & patio!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Relax and revive in this airy, modern and beautifully appointed 2600 square ft. Cape Cod home in a lovely secluded neigh ...
From $766 per night (USD)
VRBO
From $1780 per night (USD)
VRBO
Ocean front, pets ok, private beach, AC, Wifi
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
4 Bedroom - 4 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $1780 per night (USD)
VRBO
From $497 per night (USD)
VRBO
Three Bedroom -- Charming, Newly Renovated Cape Cottage - Sandy, Private Ocean Beach Just 500 Ft. Away
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming Renovated Cape Cottage with Sandy Private Ocean Beach * * * * See end of this description for informat ...
From $497 per night (USD)
VRBO
From $1013 per night (USD)
VRBO
Short Distance to Downtown Chatham -- 2/10's mile to Oyster Pond Beach Area
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
One block to Downtown Chatham and 1/2 mile to Oyster Pond, a Nice Saltwater Inlet with Sandy Beach and Bathhouse * * ...
From $1013 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Renovated, modern Chatham beach house with lots of cozy charm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This charming beach house has just been gut renovated and decorated with a modern but cozy, beachy feel. The house is lo ...
From $469 per night (USD)
VRBO
From $1084 per night (USD)
VRBO
Sprawling 5 BR Chatham Escape / Endless Outdoor Living & Entertaining Choices
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Completely renovated in 2017, this classic Cape is the perfect Chatham beach house. Offering an open flow layout with fi ...
From $1084 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Location is Everything! Walk to 3 of North Chatham's Most Scenic Salt Water Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's covete ...
From $516 per night (USD)
Expedia
Click For Pricing
VRBO
Bright & Spacious Ridgevale Beach Getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Close to Ridgevale Beach! This spacious 4 bedroom, 3 bath vacation home is well maintained and just under a mile to popu ...
Click For Pricing
VRBO
From $2408 per night (USD)
VRBO
FIVE BEDROOM -- MAGNIFICENT WATER VIEWS OF PLEASANT BAY AND ATLANTIC OCEAN.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Panoramic Saltwater Views of Nauset Beach, Strong Island, Bassing Harbor and Pleasant Bay with Private Beach * * * ...
From $2408 per night (USD)
VRBO
$North Chatham - Charming \Stones Throw\ (2130)$
From $603 per night (USD)
VRBO
North Chatham - Charming \"Stones Throw\" (2130)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features ...
From $603 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Totally renovated cottage steps to Ridgevale beach via private path and bridge!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Completely renovated in 2021! Our cottage is the perfect choice for families on vacation or anyone who’s looking for the ...
From $453 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $658 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham ...
From $391 per night (USD)
VRBO
From $553 per night (USD)
VRBO
Steps to Chatham Center & Lighthouse Beach - charming home with central AC
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Steps from Chatham Center and a short walk to Lighthouse Beach, our home is the perfect spot for families and couples lo ...
From $553 per night (USD)
VRBO
From $361 per night (USD)
VRBO
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, res ...
From $361 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Modern, RENOVATED, 3-bed PeachTree House
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Chatham's Peach Tree Cottage is NEWLY RENOVATED and minutes from the beach on a quiet residential cul-de-sac surrounded ...
From $389 per night (USD)
VRBO
From $818 per night (USD)
VRBO
Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This stunning home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, res ...
From $818 per night (USD)
VRBO
From $991 per night (USD)
VRBO
Four Bedroom home with Water Views of Saltwater Millpond & Mitchell River -- Close to Town and Oyster Pond Beach.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
3200 Square Foot Cape with Spectacular Water Views of Millpond, the Mitchell River and Stage Harbor in the Distance. * ...
From $991 per night (USD)
VRBO
From $1888 per night (USD)
VRBO
Booking for Summer 2025!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Heated Pool and hot tub! Close to Chatham Bars Inn and downtown Chatham. Perfect location for a small or large family/fr ...
From $1888 per night (USD)
VRBO
From $599 per night (USD)
VRBO
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, n ...
From $599 per night (USD)
VRBO
From $1553 per night (USD)
VRBO
Gracious home 200 yards to private beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This beautiful Cape Cod "gem" was built as a barn in the 1800s and converted to a home by our grandparent's in the 1950s ...
From $1553 per night (USD)
VRBO
From $544 per night (USD)
VRBO
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in ...
From $544 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Apres Sea - Chatham 4 Bedroom w/ Central AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Ideal location just minutes to bike trail, beaches and downtown Chatham! This home is represented by Nauset Rental, a l ...
From $923 per night (USD)
Expedia
From $544 per night (USD)
VRBO
Walk to Chatham Center or bike the Cape Cod Rail Trail!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Wonderful summer rental, filled with new furnishings and centrally located in Chatham! The Cape Cod Rail Trail is right ...
From $544 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
.... PET FRIENDLY! ... Recently updated, this classic summer beach cottage is a quick walk to popular Ridgevale Beach! A ...
From $386 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Luxury Chatham Town Home. Close to town & beaches!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Sunlight filled luxury town home overlooking a beautiful pond, with three floors of living space. Located less than a mi ...
From $346 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Fantastic Rooftop Deck * 3 Min Walk to Ocean Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In a Few Words Walk to the beach from this classic New England cottage. Head to the rooftop deck for coffee or cocktai ...
From $660 per night (USD)
Expedia
From $844 per night (USD)
VRBO
Family Friendly Home with Private Bog View-Close to 2 beaches & town center.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly remodeled in 2020, this designer 4 BR, 3 full bath house sleeps 10 (8 preferred) and has everything you need to ma ...
From $844 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Excellent Chatham Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $551 per night (USD)
VRBO
From $600 per night (USD)
VRBO
Secluded Chatham Cape Cod House Stage Harbor Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor ...
From $600 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy your quiet family get-away in a lovely, newer construction beautifully decorated cape with central air. Just a co ...
From $513 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Lovely Stage Harbor Estate Guest House W/Private Beach to Use
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Lovely guest house on quiet and picturesque Stage Harbor! Right on town way with 30 second walk to the water and use of ...
From $389 per night (USD)
VRBO
From $790 per night (USD)
Expedia
Near beach and town, private, AC, pet friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $790 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cape Cod style home with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham neighborhood. ...
From $372 per night (USD)
VRBO
From $1081 per night (USD)
VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
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 $1081 per night (USD)
VRBO

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