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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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)
$180 - $230/night
$1,200 - $3,600/week
Calendar Updated Feb 9 2010

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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Lovely home in Hardings Beach Hills, walk to the beach & neighborhood dock

— Property 136294
Chatham cottage rental - Front of house
3 Bedrooms, Sleeps 7,
Cottage, 1 Bathroom, 1 Half Bath, beach, near the ocean, satellite or cable
Rates - per property (USD)
$1,700/week
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Completely Remodeled 4 bedroom 2 Bath

— Property 246676
Chatham house rental
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$1,200 - $2,000/week
Calendar Updated Feb 9 2010

Property Review

This place has 4 bedrooms and 2 bathrooms which are clean and nice to live-in. One room is smaller than the 3 because it seems to be an office converted to a bedroom. The kitchen is fully...
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Now Booking Summer in CHATHAM

— Property 140384
Chatham house rental - Charming home in South Chatham
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, village, pets considered
Rates - per property (USD)
$900 - $2,200/week
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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 Feb 9 2010

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 Feb 9 2010

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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Beautiful Waterviews Steps to Beach

— Property 7035178h
Chatham house rental - Front
4 Bedrooms, Sleeps 9,
House, 3 Bathrooms, children, coffee maker
Rates - per house (USD)
$2,400 - $3,250/week
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The quintessential beach house!

— Property 152122
Chatham house rental
3 Bedrooms, Sleeps 8,
House, beach, terrace
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Rate Just Reduced! Save/week Brand New Cockle Cove Vacation Home

— Property 105921
Chatham house rental - quiet, last house cul-du-sac, sea shell driveway
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$2,250 - $3,250/week
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ENJOY YOUR 2010 SUMMER VACATION IN OUR BEAUTIFUL SECLUDED HOME.

— Property 123634
Chatham house rental - Front View
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, town, garden
Rates - per property (USD)
$1,500 - $2,500/week
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17 Whidah Rd, in Prestigious No. Chatham w/Private Beach

— Property 173891
Chatham house rental - 17 Whidah Road
6 Bedrooms, Sleeps 14,
House, 3 Bathrooms, 1 Half Bath, near the ocean, town, air-conditioning
Rates - per property (USD)
$2,000 - $4,500/week
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380 Pleasant St. Breathtaking Oceanview 4 Bedroom / 2 bath home

— Property 105881
Chatham house rental - View from Deck
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, balcony
Rates - per property (USD)
$1,500 - $3,700/week
Calendar Updated Feb 8 2010

Property Review

The neighborhood was wonderful and quiet and of course nothing but Sound in our front yard. House is lovely and very modern but needs a few touchups and some TLC in the Kitchen. I rented toward...
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Chatham Village home

— Property 164161
Chatham house rental - Front of house
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, village, garden
Rates - per property (USD)
$2,700/week
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Chatham's Best - Everything You Need For A Great Vacation

— Property 126131
Chatham house rental - Front side of house
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, near the ocean, town, pets considered
Rates - per property (USD)
$1,600 - $3,000/week
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Barcliff Beachhouse - Walk to Town and Beach

— Property 194312
Chatham farmhouse rental - Front
4 Bedrooms, Sleeps 8,
Farmhouse, 2 Bathrooms, 1 Half Bath, beach, downtown, internet access
Rates - per property (USD)
$2,900 - $3,500/week
Accepts Online Payments
Calendar Updated Feb 8 2010

Property Review

Our family of 5 greatly enjoyed this 4 bedroom home we rented in Aug. 2009. The fishing pier, beach and town of Chatham were easy walks of 10 - 15 minutes. Both upstairs baths were recently and...
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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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*Chatham Classic* Beautiful Water Views

— 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
$2,150 - $4,550/week
Calendar Updated Feb 8 2010

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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Spacious Chatham Condo, 2 baths, Walk to Ridgevale Beach

— Property 108744
Chatham condo rental - Spacious Condominium
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$1,500/week
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Newly Renovated Home Steps from Ridgevale Beach

— Property 136873
Chatham house rental - Quiet setting; extensive renovations inside & out
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, near the ocean, internet access
Calendar Updated Feb 8 2010

Property Review

We had a great vacation! The weather was sunny almost all week, only two cloudy/rainy days but we managed just fine with some biking, shopping and a movie. The boys loved the beach and it was so...
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Beautiful 3-bedroom near ocean beach; gorgeous views

— Property 204633
Chatham house rental - Street view of house
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, near the ocean, pets considered
Rates - per property (USD)
$1,500 - $2,500/week
Calendar Updated Feb 8 2010

Property Review

We just came back from our 9 day stay at this rental property. This house is perfect for adults, an 11 month old child and a family pet. This house was spotless and in great condition. It had...
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Charming Cape Home Near Ridgevale Beach - The Best Family Beach in Chatham

— Property 105862
Chatham house rental - 82 Deering Drive
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, beach, near the ocean, internet access
Rates - per property (USD)
$1,250 - $1,800/week
Calendar Updated Feb 8 2010

Property Review

This is a comfortable property for 6 people. Our family had fun. The deck outside is great to BBQ and have dinners. The beach is walking distance as promised and it is a very good for smaller...
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Charming Home, Close to Beach

— Property 109420
Chatham house rental
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, near the ocean, internet access
Calendar Updated Feb 8 2010

Property Review

This was our first visit to Cape Cod and we couldn"t have chosen a nicer village or more beautiful cottage to stay in! The cottage has everything you could want or need and is in a lovely location...
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Charming One Bedroom Cottage, Walk to Ocean Beach - Avail. All Seasons

— Property 151010
Chatham cottage rental - Interior - Bedroom
1 Bedroom, Sleeps 2,
Cottage, 1 Bathroom, beach, village, garden
Rates - per property (USD)
$700 - $900/week
$700/month
Calendar Updated Feb 8 2010

Property Review

We rented this cute little cottage and were not let down. The beach is right down the road and downtown Chatham is just minutes away. The property is clean, well-maintained, and in a quite...
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Oceanside - Shore Road Location - Chatham, MA

— Property 305569
Chatham house rental - Oceanside view of Briggs House
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$2,900 - $6,900/week
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Immaculate, Charming Home - On Chatham's Bike Trail - Perfect For Couples!

— Property 203270
Chatham house rental - Front View in our Lovely Cul-de-sac Neighborhood.
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, village, air-conditioning
Rates - per property (USD)
$1,400 - $1,900/week
Calendar Updated Feb 7 2010

Property Review

We could not fault this property nor the people who owned it.The house was immaculate and very well equiped,right down to everything you would need for the beach.My daughter particularly liked the...
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Luxury Home - Shore Road - near Chatham Bars Inn

— Property 212938
Chatham house rental - Main House - Ocean Side
4 Bedrooms, Sleeps 8,
House, 4 Bathrooms, 1 Half Bath, beach, garden
Rates - per property (USD)
$2,900 - $6,900/week
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Sunny house with large deck and yard on private road near beach

— Property 204361
Chatham house rental - Front view
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$175/night
$1,550/week
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Exclusive Chatham Property - Brand New

— Property 226009
Chatham house rental
3 Bedrooms, Sleeps 10,
House, 3 Bathrooms, 1 Half Bath, beach, internet access
Rates - per property (USD)
$1,000/night
$3,500 - $5,000/week
$20,000/month
Calendar Updated Feb 7 2010

Property Review

We all want to thank you so very much for the opportunity to stay at your house in Chatham .The home is absolutely beautiful –a great layout with such impressive attention to the details that make...
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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 Feb 6 2010

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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Charming Chatham Vacation Home Walk to Beach & Tennis

— Property 125545
Chatham house rental - Front view of house
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$1,300 - $2,200/week
Calendar Updated Feb 6 2010

Property Review

The house was immaculate and very roomy. Forest Beach was a 5 min walk..although small, it was the quintissential cape beach. We loved the huge screened in porch in the evenings for cocktails...