Chatham Rentals
- From $469 per night (USD)
VRBO
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 $469 per night (USD)VRBO
- From $520 per night (USD)
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 ...
From $520 per night (USD)Expedia
- From $385 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 $385 per night (USD)VRBO
- From $1571 per night (USD)
Expedia
Beautiful 5 BR property with pool and hot tub!
- Bedrooms:
- 5
- Bathrooms:
- 5
- 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 $1571 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Fantastically located Chatham house - New patio, refurbished
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fantastically located Chatham house - New patio, refurbished ( PET FRIENDLY) Location of the House - Highly sought- ...
From $371 per night (USD)VRBO
- From $568 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 ...
From $568 per night (USD)Expedia
- From $1071 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 $1071 per night (USD)VRBO
- From $395 per night (USD)
VRBO
172) Perfect for families!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream getaway!This stunning property offers a memorable retreat. 2,176 of living space provides plenty o ...
From $395 per night (USD)VRBO
- From $1368 per night (USD)
VRBO
2 Adjacent Homes on 6-acre Chatham Estate. Water views and access. Tennis & more
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 18
Welcome to Camp Moonpenny- a 6 acre property in the Sears Point area of Chatham. While only 2 miles from Main Street att ...
From $1368 per night (USD)VRBO
- From $521 per night (USD)
VRBO
NEW LISTING! Perfect family home, short walk to Chatham!
- Bedrooms:
- 3
- 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 $521 per night (USD)VRBO
- From $309 per night (USD)
VRBO
CHATHAM - 3 BLOCKS TO SANDY BEACHES, RESTAURANTS. PRIVATE YARD, LINENS INC, MINT
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
CHATHAM - AVAIL as of 4/15/2024: AVAILABLE MAY, MOST OF JUNE, SEPT & OCT and the following pockets: OPEN July 4 - 10 (6- ...
From $309 per night (USD)VRBO
- From $1900 per night (USD)
VRBO
Oyster Pond Waterfront - Chatham, Massachusetts
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
Capture spectacular sunrises, seasonal fireworks, and everything in between via the unobstructed panoramic water and tow ...
From $1900 per night (USD)VRBO
- From $1360 per night (USD)
VRBO
Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
We loved seeing the different groups who came through our house this year. We had bachelorette parties, multi-generation ...
From $1360 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Short Walk to Beautiful Ridgevale Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet, family neighborhood, a short stroll to the beach. 2 bedroom, 1 bath, outdoor shower, large deck to enjoy your mor ...
From $340 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
Alluring, Upscale in Chatham, Striking Water View, Separate Guest House: 081-C
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties. Alluring, Upscale in Chatham, Striking Water View, ...
From $1000 per night (USD)VRBO
- From $858 per night (USD)
VRBO
On the water with amazing views! Dogs welcome!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia rental home. Comfort and charm abound in this updated 18th Century seaside farmhouse (four bedrooms and ...
From $858 per night (USD)VRBO
- From $965 per night (USD)
VRBO
Luxury condo with all amenities. Pool tennis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in th ...
From $965 per night (USD)VRBO
- From $1286 per night (USD)
VRBO
Luxury condo with pool, tennis and waterviews!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond. Beaut ...
From $1286 per night (USD)VRBO
- From $905 per night (USD)
VRBO
Luxury condo in Chatham with amenities!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the ...
From $905 per night (USD)VRBO
- From $1174 per night (USD)
Expedia
Chatham Resort Style Quality with Heated Pool, Close to Everything: 364-C
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
This property is professionally managed by Pretty Picky Properties Chatham Resort Style Quality with Heated Pool, Close ...
From $1174 per night (USD)Expedia
- From $153 per night (USD)
VRBO
Sunny, Cape-style home with a game room, yard, firepit, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $153 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Charming Chatham home, close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
This lovely cottage is a short distance to South Chatham's breath taking beaches. Newly renovated kitchen and updates th ...
From $425 per night (USD)VRBO
- From $372 per night (USD)
VRBO
Direct Private Beach Access
- 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 $372 per night (USD)VRBO
- Click For Pricing
VRBO
Walk to Beach and Town, newly renovated 4\/BR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy easy access to everything from this perfectly located home base. Located in historic Chatham Village, this 1850's ...
Click For PricingVRBO
- Click For Pricing
VRBO
Welcome to Daddy's Mink!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Daddy's Mink; a stunning four bedroom home ideally located outside of downtown Chatham. Inside and out, this property ha ...
Click For PricingVRBO
- From $386 per night (USD)
Expedia
Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Awesome Location! Right on the Chatham "Loop", it is Perfect for Long Walks! This 4-bedroom Cape House is close to town ...
From $386 per night (USD)Expedia
- Click For Pricing
VRBO
AFFORDABLE AND COMFORTABLE. SHORT DRIVE TO NANTUCKET SOUND!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Reasonably Priced, Charming Rental Located on a little side street, and just a short drive to Nantucket Sound beaches ( ...
Click For PricingVRBO
- From $921 per night (USD)
Expedia
Spacious Custom Chatham Home w\/Pool, Guest Cottage & Water Views: 051-C
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties. Spacious Custom Chatham Home w/Pool, Guest Cottage ...
From $921 per night (USD)Expedia
- From $143 per night (USD)
VRBO
Townhouse-style condo at The Hammond House located across from Lighthouse Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lighthouse Beach area! Townhouse-style condo at The Hammond House is located right across from Lighthouse Beach. Spend y ...
From $143 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Pet friendly home with large backyard!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Enjoy your Chatham vacation at this spacious, 5 bedroom, 2 bath home. Offering 2 queens, a bunk bed and 4 twins, and a t ...
From $554 per night (USD)Expedia
- From $1251 per night (USD)
VRBO
Great Cockle Cove Home!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Family Retreat Destination! Let this 7 bedroom, 5 1/2 bathroom home serve as your luxurious home base for a multi-gener ...
From $1251 per night (USD)VRBO
- From $638 per night (USD)
VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
- Bedrooms:
- 2
- 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 $638 per night (USD)VRBO
- Click For Pricing
VRBO
Walk to beach and breathtaking views of Red River Marsh
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
New 2021 Listing! If you are looking for stunning views on a private deck for optimal outdoor living overlooking a windi ...
Click For PricingVRBO
- From $2269 per night (USD)
Expedia
The Barn at Hardings Beach
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Unique property offering a 4 bed 3 bath main house and a 3 bed 1.5 bath barn. The basement of the barn is set up as a ...
From $2269 per night (USD)Expedia
- From $3215 per night (USD)
VRBO
Luxury Chatham Vacation Rental w\/ Heated Pool and Spa
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 12
LISTING ALERT! 6/23/24 TO 6/29/24 OPEN FOR 5 OR 6 NIGHT STAY! Welcome to 84 Doane Road in Chatham, MA, where opulence m ...
From $3215 per night (USD)VRBO
- From $985 per night (USD)
VRBO
Newly Remodeled Seaside Getaway with Forest Beach in your backyard!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Newly renovated home with ocean views and Forest Beach right in your backyard. Swim, lounge, kayak, hike, or play tennis ...
From $985 per night (USD)VRBO
- From $1715 per night (USD)
VRBO
Luxury Chatham Home w\/ Heated Pool and Spa
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your luxurious vacation rental in the exclusive enclave of Chatham, MA! This brand new construction boasts th ...
From $1715 per night (USD)VRBO
- From $719 per night (USD)
VRBO
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Ren ...
From $719 per night (USD)VRBO
- From $844 per night (USD)
VRBO
Chatham~Lake Front~Shark Free Swimming!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This phenomenal home has been completely renovated over the past few years down to the addition of central air, wood flo ...
From $844 per night (USD)VRBO
- From $643 per night (USD)
VRBO
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Exquisite Chatham Home, Easy Access to Town, Bike Tr ...
From $643 per night (USD)VRBO
- From $1178 per night (USD)
VRBO
Superb, Upscale Waterfront in North Chatham: 078-C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This Property is professionally managed by Pretty Picky Properties. Superb, Upscale Waterfront in North Chatham Sleeps ...
From $1178 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Luxurious Home with Pool & Game Room in Cape Cod
- Bedrooms:
- 5
- 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 $900 per night (USD)VRBO
- From $210 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 $210 per night (USD)VRBO
- From $345 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, loca ...
From $345 per night (USD)Expedia
- From $217 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 vacation ho ...
From $217 per night (USD)VRBO
- From $870 per night (USD)
VRBO
Beach Cottage 4BD\/2BATH (2,138 sqft)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Beautifully renovated 4 BR/2BA bath Cape (2,138 sqft) and just a mile from Hardings Beach! Enjoy the updated kitchen, l ...
From $870 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Perfect Chatham Retreat | Access To Lovers Lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
*Cancellation policy at end of property description.* Enjoy your best days of summer at this 2BR + Bonus custom home ...
From $550 per night (USD)VRBO
- From $1068 per night (USD)
Expedia
Tastefully appointed new home located at the end of a cul-de-sac!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tastefully appointed home located at the end of a cul-de-sac with plenty of living area and beautiful outdoor space. Com ...
From $1068 per night (USD)Expedia
- From $200 per night (USD)
VRBO
The Whistling Whale - Fantastic Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Whistling Whale - Fantastic Location!! Charming one bedroom, upstairs apartment with a queen bed and fabulous views ...
From $200 per night (USD)VRBO
- Click For Pricing
Expedia
Vacation on Library Lane in the heart of downtown Chatham!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation on Library Lane in the heart of downtown Chatham! This newly renovated home that sleeps 8 in 2 queens, 2 twins ...
Click For PricingExpedia
- From $1109 per night (USD)
VRBO
Gorgeous Cape Cod getaway with patio, grill, sun room, fireplace, AC, & W\/D
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Deer Meadow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1109 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Chatham Beach Cottage + loft Walk to the Beach
- Bedrooms:
- 2
- 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 $300 per night (USD)VRBO
- Click For Pricing
Expedia
Secluded hilltop home at Chatham, with a fenced yard, Pet\/family\/work-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** New Installed Ductless Mini Split heating/AC System *** Nestled atop a secluded hill overlooking the picturesque Mon ...
Click For PricingExpedia
- From $970 per night (USD)
Expedia
Dog Friendly! Half mile to Hardings Beach, newly updated, modern coastal chic, great outdoor space
- Bedrooms:
- 4
- 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 $970 per night (USD)Expedia
- From $675 per night (USD)
VRBO
Charming colonial gem with multiple decks, gas grill, patio, and central AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $675 per night (USD)VRBO
- Click For Pricing
Expedia
Spacious Cape - Large Private Backyard, 3 Decks!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
All bathrooms and kitchens recently renovated. Fast 1GB internet, full cable, multiple living areas, work from home frie ...
Click For PricingExpedia
- From $385 per night (USD)
VRBO
Charming 3b\/2ba 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 $385 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Serene home near downtown with furnished deck - walk to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy Cape Time Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $286 per night (USD)Expedia
- From $900 per night (USD)
VRBO
Charming and updated home with private gardens and patio!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming and updated home with private gardens and patio! Located on "The Loop", this vacation rental that sleeps 8 is g ...
From $900 per night (USD)VRBO
- From $654 per night (USD)
Expedia
Refreshed Interior Central AC WIFI Large Yard Deck Great Chatham Location
- 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 $654 per night (USD)Expedia
- Click For Pricing
VRBO
Charming new 3Bd Rm 4 bath home .6mi to Ridgevale Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Newly built home, app 2900 sq feet, The 1st floor includes a master bedroom with private bath with tub/shower, king siz ...
Click For PricingVRBO
- From $386 per night (USD)
Expedia
Enjoy Classic Chatham Charm and Easy Stroll to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
<p>Located in Chatham, this welcoming vacation home lets you experience it all. Cape Cod Beaches is within an easy 13-mi ...
From $386 per night (USD)Expedia
- Click For Pricing
Expedia
Walk to Everything From this Light and Bright Home Near Town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Take advantage of the quick walk to the Chatham Anglers' Ball Field, the playground and Main Street from this recently u ...
Click For PricingExpedia
- From $618 per night (USD)
VRBO
Contemporary 4bedroom home near beach.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax with the whole family at our peaceful 4 bedroom home. Recently renovated with 2 full baths and 2 living room ...
From $618 per night (USD)VRBO
- From $571 per night (USD)
VRBO
Lovely 3 BR Home in Harbor Coves, North Chatham...Peaceful Setting!
- Bedrooms:
- 3
- 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 ...
From $571 per night (USD)VRBO
- From $799 per night (USD)
Expedia
Walking distance to downtown, CBI, Fish Pier, Veteran's Field, and beaches.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned within a comfortable walking distance to downtown Chatham, Chatham Bars Inn, the Chatham Fish Pier, ...
From $799 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Amazing Home, Private Pool, Walk to Downtown Chatham!
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 10
This exceptional property offers ultimate luxury nestled in an exclusive neighborhood steps to Chatham Village. Overlook ...
From $1500 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Lovely 1-bedroom loft-with an incredible view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Have fun with the whole family at this stylish place. We are so exited to share this newly completed space whit you! ...
From $300 per night (USD)VRBO
- Click For Pricing
VRBO
Spacious and beautiful home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful and welcoming property for a group of family or friends looking to have a wonderful time. Quiet and peaceful ...
Click For PricingVRBO
- From $775 per night (USD)
VRBO
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w\/ Pond Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*** New Listing in 2023 *** Marta (my wife) and I are two Canadians who now call Massachusetts our home. Our lovely ...
From $775 per night (USD)VRBO
- From $118 per night (USD)
VRBO
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Riviera Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $118 per night (USD)VRBO
- From $438 per night (USD)
VRBO
Newly Renovated Cape House .9Miles from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to Jean's Dream a charming Cape house in South Chatham, MA. This delightful newly renovated rental features 2 bed ...
From $438 per night (USD)VRBO
- From $455 per night (USD)
VRBO
Newly Renovated Chatham Cape House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Indulge in a memorable stay at Cockle Cottage in Chatham, MA. This inviting rental boasts 2 bedrooms, 1 bathroom and com ...
From $455 per night (USD)VRBO
- From $630 per night (USD)
VRBO
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This charming, tastefully decorated, and bright home includes a cheerful yellow fully equipped kitchen with a unique isl ...
From $630 per night (USD)VRBO
- From $857 per night (USD)
VRBO
Located in quiet Riverbay directly on the river; kayak to Jacknife Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
OFF SEASON RATES REDUCED!! Kayak to Pleasant Bay on Muddy River straight from the backyard (kayaks are provided). This ...
From $857 per night (USD)VRBO
- From $652 per night (USD)
Expedia
Views of Eastward Ho Golf Course from the backyard!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
North Chatham gem offers views of Eastward Ho Golf Course from the backyard! Antique Cape style home that sleeps 8 peopl ...
From $652 per night (USD)Expedia
- From $745 per night (USD)
VRBO
KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
***KAYAK TO PLEASANT BAY FROM YOUR BACK YARD! KAYAKS PROVIDED! OPEN YEAR ROUND Spacious five bedroom, four bath ho ...
From $745 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Steps to Oyster Pond Beach and Downtown Chatham from this beautifully landscaped, contemporary 3 bedroom home, located o ...
From $600 per night (USD)Expedia
- From $929 per night (USD)
VRBO
Steps from Ridgevale Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Steps from Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed 3 bedroom (king, 2 ...
From $929 per night (USD)VRBO
- From $1214 per night (USD)
Expedia
Spacious Waterfront Home on Ryder's Cove! Pet Friendly too!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Contemporary 4 bedroom home located on Ryder's Cove in North Chatham. Plenty of space to spread out, with different liv ...
From $1214 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Updated 6 Bedroom Home Close to Everything!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Cranberry Corners is the perfect house for your extended family vacation! DOGS WELCOME! Plenty of space to spread out, ...
From $430 per night (USD)VRBO
- From $814 per night (USD)
VRBO
Chatham Seascape
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This home is represented by Nauset Rental, a local vacation rental management company. The perfect vacation destinatio ...
From $814 per night (USD)VRBO
- From $535 per night (USD)
VRBO
Beautiful 3 bedroom Cape with spacious deck and hot tub
- Bedrooms:
- 3
- 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 ...
From $535 per night (USD)VRBO
- Click For Pricing
Expedia
Downtown Chatham - Charming & Convenient
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming 3 bedroom 2 bath Cape home located in the heart of Chatham. The lovely fenced in Back Yard and deck provid ...
Click For PricingExpedia
- From $486 per night (USD)
VRBO
Walk to The Monomoy Wildlife Sanctuary. Great space for relaxing and entertaining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spend your vacation by the beach! Charming 3 bedroom, 2 bath that can sleep 6 with 1 double bed, 2 twins, and a king in ...
From $486 per night (USD)VRBO
- From $423 per night (USD)
Expedia
Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc. Completely remodeled to perfectio ...
From $423 per night (USD)Expedia
- From $336 per night (USD)
VRBO
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 nat ...
From $336 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Bright Charming South Harwich Property, Private Backyard, Mini Splits
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This quaint 2-story Gambrel style Cape house is located on a quiet cul-de-sac conveniently located off Route 28 between ...
From $400 per night (USD)Expedia
- From $500 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 $500 per night (USD)VRBO
- From $714 per night (USD)
Expedia
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 $714 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Dog-friendly home with yard, patio, grill, & fireplace - great location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Whale's Tales Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $286 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Chatham Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a peaceful, quiet escape in beautiful Chatham on Cape Cod. Our home is a short walk to town and Oyster Pond. 7 m ...
From $349 per night (USD)Expedia
- From $986 per night (USD)
VRBO
Charming and in town!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming and in town! Leave the cars parked and walk to everything. A few minute's walk to downtown will bring you to th ...
From $986 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Perfect family vacation rental!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home is the perfect spot for your family vacation! Located in a quiet neighborhood less than a mile into downtown ...
From $490 per night (USD)Expedia
- From $341 per night (USD)
VRBO
Classic, airy Chatham cottage minutes from beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**House is cleaned, disinfected & aired out between guests** Welcome to Cranberry Cottage, a cozy 2 BR, 1 BA cottage ce ...
From $341 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Historic Cottage on White Pond, near Downtown Chatham and beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Affectionately named the "Chit-Chat", this classic 1920's 2 bedroom Cape Cod cottage is near downtown and Chatham's best ...
From $273 per night (USD)Expedia
- From $1100 per night (USD)
VRBO
A short stroll to Hardings Beach - Perfect Cape Cod Getaway Begins Here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Cancellation policy at end of property description.* Your search for the perfect Cape Cod getaway begins and ends ri ...
From $1100 per night (USD)VRBO
- From $530 per night (USD)
Expedia
5 Bedroom Chatham Retreat on Quiet Street
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious 5 bedroom home in a great location in Chatham! This home can comfortably accommodate your entire family. Beauti ...
From $530 per night (USD)Expedia
- From $999 per night (USD)
VRBO
Relax and enjoy this stylish home in Chatham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Picture yourself enjoying your next vacation at this newly renovated 3 bed/2.5 bath home. 4 min to beach & town. Cathedr ...
From $999 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Newly Renovated and Ideally Located \/ Close to Chatham's Idyllic Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated and Ideally Located, this Two-Bedroom Home is Close to Downtown, the Chatham A's Ballpark, the Fish Pier ...
From $390 per night (USD)Expedia