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From $658 per night (USD)
VRBO
Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy your vacation at this lovely North Chatham home. This charming, sunny and spacious, arts and crafts bungalow is co ...
From $658 per night (USD)
VRBO
From $854 per night (USD)
Expedia
Chatham-Walk to Town/Beach-Multi Family Friendly
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
It's all about location. You will have the perfect family vacation in this 5 bedroom, 4.5 bath bathroom lovingly cared ...
From $854 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Chatham Village - Adorable Studio Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $212 per night (USD)
VRBO
From $608 per night (USD)
Expedia
Newly updated home sleeps 7, AC, free WIFI, half mile to town
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 Bedroom - 2 Baths - Sleeps 7 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $608 per night (USD)
Expedia
From $628 per night (USD)
VRBO
GREAT LOCATION - Water View, Walk to beach & Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location, Location, Location! Enjoy all the Chatham has to offer! Views of Claflin Landing Beach, Chatham Harbor, No ...
From $628 per night (USD)
VRBO
From $625 per night (USD)
Expedia
4 Bedrooms, 2 Baths, Sleeps 8-10
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Location! Location! Location! The “Woodford Reserve” for fun and respite! This is classic cape cod home with four bedro ...
From $625 per night (USD)
Expedia
From $815 per night (USD)
VRBO
Fantastically located Chatham house - DISCOUNTED - New patio, refurbished
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Location of the House - Highly sought after Chatham house - corner property which is a walking distance from Historic Do ...
From $815 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Comfort and charm abound in this updated 18th Century seaside farmhouse (4 bedrooms and 3 baths!) situated on more than ...
From $647 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $263 per night (USD)
VRBO
From $469 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 $469 per night (USD)
Expedia
From $382 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 $382 per night (USD)
VRBO
From $744 per night (USD)
Expedia
5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Chatham Beach House with deeded rights to a path to Hardings Beach as well as to a path to Oyster River Boatyard. Five ...
From $744 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Chatham Village: Large, Newly-Renovated 1 Bedroom Apartment in Antique Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
** We've just completed a major renovation of Ship's Light! Having stood the test of time for almost 200 years, the hous ...
From $252 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Chatham Pearl on Oyster River Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $255 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Newly Open - Aug 23-30!! Spacious 3 BR with AC. Walk to Beach! Pet Friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming, air-conditioned Chatham home has recently been upgraded. It has new living room furniture and fresh paint ...
From $509 per night (USD)
VRBO
From $468 per night (USD)
Expedia
A well-appointed getaway near beach, Wifi, Gas grill, Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chatham Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $468 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Sunny Updated Chatham Village 2 Bedroom Condo W/ Large Private Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Fantastic location! Thoughtfully updated with all new furnishings! Beautiful light filled 2 bedroom, 2 bath second floo ...
From $479 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
B By the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $341 per night (USD)
Expedia
From $1783 per night (USD)
VRBO
Updated Chatham Inn Home | Spacious Deck & Private Heated Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Stepping Stones -- Old Chatham Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $1783 per night (USD)
VRBO
From $619 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 $619 per night (USD)
Expedia
From $581 per night (USD)
VRBO
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air ...
From $581 per night (USD)
VRBO
From $356 per night (USD)
VRBO
1 Mi to Town & Oyster Pond Beach: Chatham Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $356 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $315 per night (USD)
VRBO
From $853 per night (USD)
Expedia
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Ocean Harbor Waterfront. Stunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with ...
From $853 per night (USD)
Expedia
From $436 per night (USD)
VRBO
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the sh ...
From $436 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Sunrise to Sunset: Bucks Creek Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $590 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Spacious Home on the Loop in Chatham
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Located on the Loop in scenic Chatham, this house rents Sunday to Sunday. The large living room opens onto a deck with ...
From $755 per night (USD)
VRBO
From $879 per night (USD)
Expedia
Pet friendly and spacious home in quiet neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $879 per night (USD)
Expedia
From $463 per night (USD)
VRBO
North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1 Bathroom - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $463 per night (USD)
VRBO
From $1163 per night (USD)
Expedia
Location and Luxury
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Har ...
From $1163 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Charming Downtown Chatham
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Charming in town apartment above retail shops overlooks the Main St. Walk to beaches, nearby shops & restaurants, band c ...
From $271 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Chatham 3 Bedroom/2 Bath Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated and spacious 3 Bedroom 2 Full Bath Home on a private 1/2 acre setting in one of Chatham's sought a ...
From $307 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
South Chatham Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $305 per night (USD)
VRBO
From $1276 per night (USD)
Expedia
Charming Chatham Cottage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
...
From $1276 per night (USD)
Expedia
From $644 per night (USD)
VRBO
Cozy Cape near Chatham Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. Our home is 1/2 mile from the qua ...
From $644 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $269 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 $269 per night (USD)
VRBO
From $792 per night (USD)
Expedia
Water View-Walk town/beach, pets considered, Linen Option
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
It's all about LOCATION-just steps from deeded access to the Mill Pond where you can launch your Kayak without ever havi ...
From $792 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Chatham-Walk to Ridgevale Beach, Pets Considered, Central Air, Bike Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
After walking by the beautiful hydrangeas and entering through the front door you will realize this house is much more ...
From $587 per night (USD)
VRBO
From $350 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 $350 per night (USD)
Expedia
From $407 per night (USD)
VRBO
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 $407 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 $377 per night (USD)
VRBO
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)
VRBO
From $364 per night (USD)
Expedia
Great Location in Chatham Walk to town shop, dine, band concert, cape baseball
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Have a wonderful time on your Cape Cod vacation! Our home includes a new deck for your summer cookouts an outdoor shower ...
From $364 per night (USD)
Expedia
From $454 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 $454 per night (USD)
VRBO
From $658 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 $658 per night (USD)
VRBO
From $404 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 $404 per night (USD)
VRBO
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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. ...
Click For Pricing
Expedia
From $401 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 $401 per night (USD)
VRBO
From $178 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 $178 per night (USD)
Expedia
From $504 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 $504 per night (USD)
VRBO
From $318 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 $318 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
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VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $514 per night (USD)
VRBO
Poppy's Place: Cape Escape for Family & Friends
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 $514 per night (USD)
VRBO
From $434 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 $434 per night (USD)
VRBO
From $899 per night (USD)
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 ...
From $899 per night (USD)
VRBO
Click For Pricing
Expedia
Charming Coastal Haven in Chatham
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 ...
Click For Pricing
Expedia
From $524 per night (USD)
VRBO
North Chatham Retreat – Renovated 3BR, 3.5BA + Bonus, 2900 Sq Ft
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Your North Chatham Retreat – A Perfect Cape Cod Getaway Located in scenic North Chatham and just minutes fro ...
From $524 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 $840 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 $840 per night (USD)
VRBO
From $787 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 $787 per night (USD)
VRBO
From $537 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 $537 per night (USD)
VRBO
From $605 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 $605 per night (USD)
VRBO
From $572 per night (USD)
VRBO
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. ...
From $572 per night (USD)
VRBO
From $401 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 $401 per night (USD)
VRBO
From $408 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 $408 per night (USD)
VRBO
From $430 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 $430 per night (USD)
VRBO
From $1545 per night (USD)
VRBO
Chatham Loop/Stage Neck/5 Bed/6 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
https://www.youtube.com/watch?v=aFmta3dZpX8 Welcome to Over The Moon located in the heart of Chatham's Gold Coast just ...
From $1545 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $526 per night (USD)
VRBO
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 $526 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $673 per night (USD)
VRBO
Perfectly Content: Walk to Schoolhouse Pond
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 $673 per night (USD)
VRBO
From $445 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 $445 per night (USD)
VRBO
From $790 per night (USD)
VRBO
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 $790 per night (USD)
VRBO
From $742 per night (USD)
Expedia
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 $742 per night (USD)
Expedia
From $537 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 $537 per night (USD)
VRBO
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 $1740 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 $1740 per night (USD)
VRBO
$North Chatham - Charming \Stones Throw\ (2130)$
From $574 per night (USD)
Expedia
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 $574 per night (USD)
Expedia
From $458 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 $458 per night (USD)
VRBO
From $347 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 $347 per night (USD)
VRBO
From $308 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 $308 per night (USD)
VRBO
From $358 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 $358 per night (USD)
VRBO
From $695 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 $695 per night (USD)
VRBO
From $650 per night (USD)
Expedia
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 $650 per night (USD)
Expedia
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 $376 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 $376 per night (USD)
VRBO
From $708 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 $708 per night (USD)
VRBO
From $313 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 $313 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 $709 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 $709 per night (USD)
VRBO
From $484 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 $484 per night (USD)
VRBO
From $330 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 $330 per night (USD)
VRBO
From $308 per night (USD)
VRBO
See the World Cup AND Enjoy a Chatham Vacation June 2026
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
90 mile (mostly highway) drive to Gillette Stadium, where some 2026 World Cup Games will be held. Enjoy a vacation in de ...
From $308 per night (USD)
VRBO
From $804 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 $804 per night (USD)
VRBO
From $6793 per night (USD)
VRBO
Your Ultimate Vacation Destination!
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
This is your ultimate vacation destination! Simply stunning, custom built home with a grand farmer's porch! Sit and sip ...
From $6793 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Happy Yellow House - Family and pet-friendly; walkable to Ridgevale Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
*Note: The minimum stay dropped to 3 nights for Jan-March! Other months are still 7 nights as a minimum. The monthly dis ...
From $594 per night (USD)
VRBO
From $616 per night (USD)
VRBO
CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $616 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Reuben Young House: Two 1st Floor King Master Suites. Close to Town & Beaches.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming circa 1820 antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oys ...
From $1001 per night (USD)
Expedia

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