Take a Chance in Chatham

Chatham Vacation Rentals, Chatham Condos, Cottages, Townhomes, Houses, Farmhouses & Estates

For your upcoming vacation on Cape Cod, head out to Chatham, Massachusetts, an old fishing and whaling community that has retained its late colonial flavor. From rustic beach rentals to quaint cottages, you’ll have a better time in a vacation home than in a single overpriced hotel room. Whether you’re looking to bring the family for a weekend getaway, or just want to get out of town for the summer, Chatham has much to offer, both indoors and out.

Consider a beach house on the ocean and spend the afternoons relaxing on the sand with your favorite novel. Don’t worry if sunbathing isn’t your thing. You won’t run out of things to do in Chatham. In fact, you’ll feel as though you’ve stepped back into time when you stroll down Main Street and view its preserved 18th century architecture. Browse through the family-owned shops, including an old fashioned candy store known for its homemade fudge. Buy tickets to a road show at the well- known Monomoy Theatre, or during the summer, catch a free concert at the Gazebo.

If you feel like exploring other parts of Cape Cod, consider taking the ferry to the Monomoy National Wildlife Refuge, home to several species of migratory birds. Or spend a day browsing through the Railroad Museum and learn more than you could from one of those coffee table books that are just for display. Cook meals in the custom kitchen of your home rental and save money to spend on local attractions, like the several art galleries and village shops that populate downtown. No matter what floats your boat, you’ll leave Chatham feeling rejuvenated, so begin planning your summer vacation today!

There are additional vacation properties that the Cape Cod peninsula has to offer. To increase your search selection of Cape Cod vacation rentals consider checking out following rental options: Dennis MA vacation rentals, Bourne area vacation homes, Eastham beach rentals, lodging in Falmouth MA, Harwich rentals, beach cottages in Orleans MA, Provincetown lodging, vacation lodging in Truro MA, Wellfleet cottages, or vacation beach rentals in Yarmouth.



Chatham MA Vacation Homes Rental

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Chatham house rental - High Tide
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, waterfront, garden
Rates - per property (USD)
$2,150/week
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North Chatham Beach Front Property close to Eastward Ho!

— Property 155403
Chatham house rental - Front of House
6 Bedrooms, Sleeps 12,
House, 4 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$4,000 - $7,995/week
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Perfect Chatham - 3 BR, 2 Bath Walk to Cockle Cove Beach and The Bike Path

— Property 158254
Chatham house rental - From the side
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$800 - $1,800/week
Calendar Updated Nov 24 2009

Property Review

This clean, newer home has everything as described. Has everything needed, from a well stocked kitchen to fun and games for the kids on a rainy day. Great place for everyone, although one bedroom...
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Chatham house rental - Beautiful five bedroom home on triple lot!
5 Bedrooms, Sleeps 11,
House, 3 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$2,500 - $4,995/week
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159 Holly Dr.

— Property 7003938h
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms
Rates - per house (USD)
$1,400/week
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Very private, Pretty, Chatham Cottage, Walk to Ridgevale beach, bike path

— Property 230732
Chatham house rental - House deck view
3 Bedrooms, Sleeps 8,
House, 1 Bathroom, beach, near the ocean, garden
Rates - per property (USD)
$250/night
$1,200 - $1,800/week
Calendar Updated Nov 23 2009

Property Review

Our family spent a week at this house in early August. The house is very private, open, bright and lovely. The yard is great for kids and there is a terrific loft for the kids to play in. The...
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Chatham cottage rental - View from water near pier and beach
5 Bedrooms, Sleeps 8,
Cottage, 1 Bathroom, 1 Half Bath, beach, waterfront, garden
Rates - per property (USD)
$400 - $500/night
$2,400 - $4,800/week
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Pristine Morris Island Road Home in Chatham

— Property 242983
Chatham house rental - Great house in a great Chatham location.
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, 1 Half Bath, beach, near the ocean, balcony
Rates - per property (USD)
$4,200 - $5,200/week
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Beautiful Home just 500 ft. from Ridgevale Beach

— Property 7030577h
Chatham house rental - Front
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, adventure, air-conditioning
Rates - per house (USD)
$1,900 - $2,950/week
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Perfect Cottage - lovely waterviews & walk to beach

— Property 159202
Chatham cottage rental - Front View - off season-see the sea on each side
2 Bedrooms, Sleeps 5,
Cottage, 2 Bathrooms, beach, waterfront, satellite or cable
Rates - per property (USD)
$175 - $250/night
$1,050 - $2,400/week
$8,640/month
Calendar Updated Nov 22 2009

Property Review

Great Cottage! Great Location! Great Vacation! What else could you ask for.......................
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Quiet Setting, walk to beach

— Property 117092
Chatham house rental
3 Bedrooms, Sleeps 8,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$175/night
$1,000 - $1,800/week
Calendar Updated Nov 21 2009

Property Review

This year (Sept 2008) it was my turn to host the 21st annual sisters weekend getaway for my 4 sisters and I. The five of us have convened annually together in many geographical locations over the...
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*Chatham Classic* Celebrate Christmas By The Sea

— Property 123592
Chatham house rental - Front Lawn Deck
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, 1 Half Bath, beach, waterfront, garden
Rates - per property (USD)
$395 - $475/night
$1,950 - $4,550/week
Calendar Updated Nov 21 2009

Property Review

We have been renting on the Cape for over 20 years and this is the best home we have ever rented. Clean, private and spacious.
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Classic North Chatham Escape

— Property 239026
Chatham house rental - Classic Cape Cod Sea Captain's Home
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, near the ocean, village, garden
Rates - per property (USD)
$2,100 - $2,700/week
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Large, pristine Chatham home, private tennis court, walk to beach and Town.

— Property 263981
Chatham house rental - Deck overlooks private tennis court.
5 Bedrooms, Sleeps 8,
House, 4 Bathrooms, near the ocean, town, tennis court
Rates - per property (USD)
$8,000/week
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Water Views! Luxury home, short walk to Hardings Beach.

— Property 179305
Chatham house rental - This is it!
5 Bedrooms, Sleeps 10,
House, 3 Bathrooms, 1 Half Bath, beach, near the ocean, jacuzzi
Rates - per property (USD)
$5,500 - $9,500/week
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Charming Antique Home for Rent in West Chatham, Massachusetts

— Property 234295
Chatham house rental - Front House with paved driveway
4 Bedrooms, Sleeps 10,
House, 4 Bathrooms, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$2,000 - $3,100/week
Calendar Updated Nov 20 2009

Property Review

We spent a week in June 2009 at this lovely home. We would certainly return, and would definitely recommend to friends. Thank you for a wonderful week! The house is beautiful and very...
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Chatham townhome rental - Front of Townhouse
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, 1 Half Bath, beach, downtown, air-conditioning
Rates - per property (USD)
$1,200 - $1,600/week
Calendar Updated Nov 20 2009

Property Review

My first experience with Cape Cod renting was great! Not only were the owners extremely helpful, but the property is in a very desirable location. And the price is incredible considering the size...
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Spectacular Ocean View on Prime Acre: Quintessentially Perfect!

— Property 106009
Chatham house rental - Frontal View of Our Tranquil Chatham Home
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, near the ocean, waterfront, air-conditioning
Rates - per property (USD)
$171 - $200/night
$1,200 - $3,400/week
$4,800 - $14,000/month
Calendar Updated Nov 19 2009

Property Review

Our girls' group loved the Chatham Home-By-The-Sea for our annual summer trip. It was spacious and contained everything we needed for a great stay. We just purchased the food for the week and...
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Newly Renovated Chatham 3 Bedroom/2 Bath Retreat

— Property 150401
Chatham house rental - Front of house
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, resort, river, air-conditioning
Rates - per property (USD)
$800 - $2,200/week
Calendar Updated Nov 19 2009

Property Review

The house was lovely, clean and close to town. We have two children and it was very nice that it had enough room for all of us to feel comfortable. We were there for First Night but unfortunately...
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Serene Setting, Walk to Beach, Off Season Rates start 8-21

— Property 211806
Chatham house rental - Sunny Natural Setting
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, tennis court
Rates - per property (USD)
$925 - $1,425/week
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Charming Cedar Street home. Walk to town and Oyster Pond

— Property 154870
Chatham house rental - 308 Cedar....Vintage charm with modern amenities!
4 Bedrooms, Sleeps 9,
House, 2 Bathrooms, beach, town, air-conditioning
Rates - per property (USD)
$1,150 - $2,550/week
Calendar Updated Nov 19 2009

Property Review

This beautiful home is perfection. Very clean and located perfectly in Chatham. It's location is in close proximity to all Chatham has to offer. The owners provide a fantastic book of local...
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Views of Nantucket Sound and Walk to Beach from Charming Cape Cod Cottage.

— Property 166797
Chatham cottage rental - Cottage Circle Drive and Parking Area
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, near the ocean, pets considered
Rates - per property (USD)
$1,000/week
$1,200 - $1,500/month
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Chatham house rental - Farmer's porch and front of house
5 Bedrooms, Sleeps 14,
House, 4 Bathrooms, near the ocean, air-conditioning
Rates - per property (USD)
$4,000/week
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Classic Chatham Village-Two Story Home

— Property 134182
Chatham house rental - Harrington House
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, 1 Half Bath, downtown, garden
Rates - per property (USD)
$1,725 - $2,450/week
Calendar Updated Nov 24 2009

Property Review

Wonderful home and location! Everything you could possibly need in a rental.
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Charming Historic Home in the Heart of Old Village

— Property 144182
Chatham cottage rental - Cozy Family Room w/Wood-Burning Fireplace
4 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, 1 Half Bath, beach, village, air-conditioning
Calendar Updated Nov 18 2009

Property Review

This is a beautiful restoration of a house in a charming town and an excellent location for both beach and town which are within a few minutes walk. We loved the feel of the house and it was very...
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Just off Hardings Beach - Chatham MA Cape Cod

— Property 227195
Chatham cottage rental - House
3 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$1,500 - $1,700/week
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Secluded North Chatham Classic with Private Beach

— Property 116155
Chatham house rental - Front of House Facing Pleasant Bay
5 Bedrooms, Sleeps 9,
House, 2 Bathrooms, 1 Half Bath, beach, waterfront, terrace
Rates - per property (USD)
$3,000/week
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WATERVIEW of Nantucket Sound; 1/2 m. to Hardings Beach

— Property 211174
Chatham house rental - Master bedroom
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$1,600 - $3,450/week
Calendar Updated Nov 17 2009

Property Review

We (2 adults and a toddler) stayed at this property in June and we all really enjoyed it. The house is very well equipped and it’s just as nice as the pictures show. There is a large deck...
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Old Village Home, 5 min. walk to Beach & Downtown

— Property 121737
Chatham house rental - Front of Home
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the ocean, town, air-conditioning
Rates - per property (USD)
$1,750 - $2,950/week
Calendar Updated Nov 16 2009

Property Review

Excellent location within walking distance of the Chatham lighthouse, the beach and the shops in Chatham Village on Main St. The house was fully equipped and had A/C though it wasn't needed during...
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Chatham Village -Walk to village & ocean.Park and Relax

— Property 105734
Chatham cottage rental
2 Bedrooms, Sleeps 5,
Cottage, 1 Bathroom, beach, downtown, garden
Rates - per property (USD)
$750 - $1,600/week