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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SPECIAL OFFER! Book before January 31, 2010 and SAVE (July 3 - August 28)
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Overlooking Lovers Lake

— Property 215972
Special Offer
Chatham house rental - Private Heated Pool
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, beach, lake, pool
Rates - per property (USD)
$2,750 - $4,250/week
Calendar Updated Nov 9 2009

Property Review

What a wonderful vacation filled with great memories. Your house was so warm and inviting. The children loved the heated pool. Thank you! Laura, John, Amanda and Shaun
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Classic Renovated Cottage near Town & Beaches

— Property 121806
Chatham cottage rental - Japanese Maples welcome you to our home
3 Bedrooms, Sleeps 6,
Cottage, 2 Bathrooms, beach, town, pets considered
Rates - per property (USD)
$1,650 - $1,850/week
Calendar Updated Nov 9 2009

Property Review

Hello! My wife and I are enjoying our last day at 60 Pondview, and have had a memorable week here at the house, and in Chatham. The house is adorable, and exemplifies Cape Cod living at it's...
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Old Harbor Road - close to town perfect for extended families

— Property 204332
Chatham house rental - The front porch for seeing and being seen
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, downtown, garden
Rates - per property (USD)
$1,500 - $3,000/week
Calendar Updated Nov 9 2009

Property Review

We enjoyed our stay at Old Harbor house. Close to Chatham and all the sights. Classically Cape Code.
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25 Ethelma Drive, Chatham

— Property 217362
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, pets considered
Rates - per property (USD)
$1,000 - $2,500/week
Calendar Updated Nov 9 2009

Property Review

We loved our stay at 25 Ethelma. The house is immaculate, beautiful and quiet. The central air conditioning was very welcome the week we stayed. The bike path is right around the corner. We would...
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Walk to Town - Great Location, Full of Charm

— Property 179236
Chatham house rental - Front of House
2 Bedrooms, Sleeps 5,
House, 1 Bathroom, beach, downtown, internet access
Rates - per property (USD)
$200 - $250/night
$1,000 - $1,600/week
Calendar Updated Nov 8 2009

Property Review

My husband and I stayed here August 9-16. The cottage is small but clean and neat as can be. The owner has done a wonderful job decorating and really capturing that Chatham charm. A short walk to...
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Immaculate, Charming Home - On The 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
Calendar Updated Nov 8 2009

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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Fun family-friendly retreat, steps to Ridgevale Beach

— Property 130469
Chatham house rental - Bright, updated Colonial, 1.5 blocks from beach
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$240/night
$1,000 - $2,700/week
Calendar Updated Nov 8 2009

Property Review

My family and I enjoyed our vacation in September of 2007 greatly. This was largely due to the fantastic stay as Si Como No. It had everything we were looking for with approximity to the beach,...
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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 8 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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Chatham condo rental - Enjoy Our Beautiful Beach . . . You'll Love It!!!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, air-conditioning
Rates - per property (USD)
$1,000 - $2,300/week
Calendar Updated Nov 7 2009

Property Review

Our family, 2 adults and 2 teenagers, had a most wonderful time in this marvellous condo. From the moment we arrived at Chatham we felt really welcome and relaxed. The terraced House was very...
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Chatham house rental - Beautiful four 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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Prestigious North Chatham 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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Classic Chatham Village-Two Story Home

— Property 134182
Chatham house rental - Harrington House
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, downtown, village, garden
Rates - per property (USD)
$1,725 - $2,300/week
Calendar Updated Nov 9 2009

Property Review

Wonderful home and location! Everything you could possibly need in a rental.
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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 5 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 5 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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Chatham-Stage Harbor-Walk to Town.

— Property 130947
Chatham house rental - Front of House
5 Bedrooms, Sleeps 12,
House, 4 Bathrooms, 1 Half Bath, downtown, near the ocean, jacuzzi
Rates - per property (USD)
$3,995 - $7,995/week
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Waterfront Condo Lighthouse & Marina -Long weekend off season special

— Property 112930
Chatham condo rental - More of our beach
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, 1 Half Bath, beach, waterfront, air-conditioning
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Chatham - Mill Pond - Stage Harbor-Water View

— Property 105239
Chatham house rental - Rear of Home-Roof Deck and Patios
5 Bedrooms, Sleeps 16,
House, 4 Bathrooms, near the ocean, town, balcony
Rates - per property (USD)
$2,500 - $7,995/week
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Spectacular water views and steps from Main St Chatham

— Property 230518
Chatham house rental - In Chatham center, yet secluded with water views
4 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, beach, waterfront, pets considered
Rates - per property (USD)
$3,800/week
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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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Newly Constructed Classic Cape - Near Ocean, Walk to Beach

— Property 116091
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, near the ocean, jacuzzi
Rates - per property (USD)
$335/night
$2,295/week
Calendar Updated Nov 4 2009

Property Review

Fantastic property in excellent location. A very quiet, safe area. Facilities in house were superb and had everything from washing machine / tumble dryer to lego and games for my children. We...
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Beautiful Home just 500 ft. from Ridgevale Beach

— Property 7030577h
Chatham house rental - Ridgevale Beach at 500 ft.
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, adventure, air-conditioning
Rates - per house (USD)
$1,900 - $2,950/week
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Charming Seaside Cottage with Private Access to Oyster River

— Property 145991
Chatham cottage rental - Entering
2 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, near the ocean, satellite or cable
Calendar Updated Nov 4 2009

Property Review

This was our 2nd. yr. staying at the Carriage House in Chatham, we love the place and plan on going back again for a 3rd. yr +. It is perfect for a family of 4 plus. The house is clean and well...
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Near Salt and Fresh Water Beaches -- Chatham

— Property 120716
Chatham house rental - Hydrangaes in Bloom
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, village, garden
Rates - per property (USD)
$1,800 - $2,300/week
$6,800 - $8,800/month
Calendar Updated Nov 3 2009

Property Review

We would like to say WOW!! Your home was more than the pictures show. Our family had a wonderful time in Chatham and your home played a big part in our vacation. The kitchen is outstanding and...
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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 - $4,350/week
Calendar Updated Nov 9 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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Private, Pretty, Chatham Cottage, Walk to Ridgevale beach, October avail

— 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 9 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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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 2 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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Completely Remodeled Cape Cod Rental (PHOTOS BEING UPDATED DAILY)

— Property 246676
Chatham house rental
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, beach, near the ocean, garden
Calendar Updated Nov 2 2009

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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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 2 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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Fall at the Cape -Enjoy our charming, spacious, comfortable home

— Property 188659
Chatham house rental - Street Entrance to the house
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$1,600 - $2,300/week
Calendar Updated Nov 2 2009

Property Review

Our family just spent a week at this Chatham home, and would start by saying it FAR exceeded our expectations. Upon arrival, we found the house to be VERY clean, and very comfortable. The...
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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