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
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, town, air-conditioning
Rates - per property (USD)
$1,700 - $1,900/week
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Chatham house rental - Exterior
3 Bedrooms, Sleeps 8,
House, 1 Bathroom, beach, village, washing machine
Rates - per property (USD)
$900 - $1,600/week
$1,000/month
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Chatham cottage on lake one mile to ocean beaches

— Property 123686
Chatham cottage rental
2 Bedrooms, Sleeps 5,
Cottage, 1 Bathroom, 1 Half Bath, lake, near the ocean, fishing
Rates - per property (USD)
$100/night
$650 - $850/week
Calendar Updated Jul 3 2009

Property Review

The pictures don't do this cottage justice. We had a beautiful week in Chatham, and the house was perfect!
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Cozy Cottage with views of Nantucket Sound

— Property 224990
Chatham cottage rental
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, beach, near the ocean, internet access
Rates - per property (USD)
$900 - $1,400/week
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Chatham cottage rental - right side of cottage
1 Bedroom, Sleeps 4,
Cottage, 1 Bathroom, beach, near the ocean, air-conditioning
Rates - per property (USD)
$1,000/week
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Chatham cottage rental - Interior - Bedroom
1 Bedroom, Sleeps 2,
Cottage, 1 Bathroom, beach, village, air-conditioning
Rates - per property (USD)
$700 - $900/week
$700/month
Calendar Updated Jul 3 2009

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...
SPECIAL OFFER! Take an additional $300 off weeks in Aug (August 1 - August 31)
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Special Offer
Chatham house rental - The front porch for seeing and being seen
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, downtown, washing machine
Rates - per property (USD)
$1,800 - $2,000/week
Calendar Updated Jul 2 2009

Property Review

We enjoyed our stay at Old Harbor house. Close to Chatham and all the sights. Classically Cape Code.
SPECIAL OFFER! Last Minute Escapes with your own Pool (July 4 - August 15)
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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, swimming pool
Rates - per property (USD)
$2,750 - $3,000/week
Calendar Updated Jul 2 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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Chatham Village home

— Property 164161
Chatham house rental - Front of house
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, village, washing machine
Rates - per property (USD)
$2,700/week
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25 Ethelma Drive, Chatham

— Property 217362
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, air-conditioning
Rates - per property (USD)
$1,500 - $2,500/week
Calendar Updated Jul 2 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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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)
$3,000/week
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Oceanfront Beach Cottage - Spectacular Views

— Property 154985
Chatham cottage rental - View of the beach from property
2 Bedrooms, Sleeps 6,
Cottage, beach, waterfront, internet access
Rates - per property (USD)
$3,200/week
Calendar Updated Jul 2 2009

Property Review

We rented "Bayberry" during the off season (April) and were delighted. The cottage was cozy, clean, and comfortable. It is cleverly situated so that we had complete privacy even though it is...
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Water view, Beautiful Sunsets

— Property 224720
Chatham house rental - House
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, near the ocean, washing machine
Rates - per property (USD)
$2,000 - $2,800/week
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Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, near the ocean, tennis
Rates - per property (USD)
$1,200 - $1,600/week
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Cape Cod - Pine Grove - Cockle Cove

— Property 200277
Chatham cottage rental - Front View - Drive-In Area
2 Bedrooms, Sleeps 5,
Cottage, 1 Bathroom, beach, tennis
Rates - per property (USD)
$100 - $150/night
$550 - $900/week
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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, air-conditioning
Rates - per property (USD)
$2,900 - $7,900/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, air-conditioning
Rates - per property (USD)
$1,725 - $2,300/week
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Chatham house rental - Beautiful four bedroom home on triple lot!
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, beach, near the ocean, accept credit card
Rates - per property (USD)
$2,500 - $4,750/week
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Chatham condo rental - More of our beach
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, 1 Half Bath, beach, waterfront, air-conditioning
Rates - per property (USD)
$800 - $1,500/week
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The quintessential beach house!

— Property 152122
Chatham house rental
3 Bedrooms, Sleeps 8,
House, beach, washing machine
Rates - per property (USD)
$2,400/week
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Chatham house rental - Bright, updated Colonial, 1.5 blocks from beach
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, washing machine
Rates - per property (USD)
$225/night
$1,000 - $2,500/week
Calendar Updated Jul 1 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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Charming Chatham Home

— Property 184598
Chatham house rental - Front of house
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, beach, near the ocean, washing machine
Rates - per property (USD)
$1,650/week
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Chatham house rental - View from back yard shows large outdoor shower
3 Bedrooms, Sleeps 8,
House, 1 Bathroom, beach, near the ocean, air-conditioning
Rates - per property (USD)
$1,200 - $2,500/week
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Charming Cottage at Ridgevale Beach

— Property 140135
Chatham cottage rental
2 Bedrooms, Sleeps 5,
Cottage, 1 Half Bath, beach, near the ocean, internet access
Rates - per property (USD)
$1,400/week
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Chatham house rental - Front of house
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, village, washing machine
Rates - per property (USD)
$150/night
$975 - $1,400/week
Calendar Updated Jul 3 2009

Property Review

We had never visited the Cape before and found this house to be in a great location to visit all around. A lovely and clean house with a nice decking area and plenty of space for the children to...
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Chatham Escape

— Property 122579
Chatham cottage rental
2 Bedrooms, Sleeps 5,
Cottage, 1 Bathroom, air-conditioning, washing machine
Rates - per property (USD)
$800 - $1,100/week
Calendar Updated Jul 1 2009

Property Review

We enjoyed our stay very much. The outdoor shower was really enjoyable. Private and relaxing. Very comfortable home for a family vacation, walking distance to everything. Thanks
SPECIAL OFFER! Cancellation Special!! (July 18 - August 1)
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Marshview at Ridgevale Beach - walk to beach

— Property 155244
Special Offer
Chatham house rental - House front
2 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, village, washing machine
Rates - per property (USD)
$2,100/week
SPECIAL OFFER! Save $500 July 4th Chatham Waterview (July 4 - July 11)
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Perfect Cottage - lovely waterviews & walk to beach

— Property 159202
Special Offer
Chatham cottage rental - Front View - off season-see the sea on each side
2 Bedrooms, Sleeps 5,
Cottage, 2 Bathrooms, beach, waterfront, washing machine
Rates - per property (USD)
$900 - $2,300/week
Calendar Updated Jun 30 2009

Property Review

Dear Jane, This is a somewhat overdue ‘thank you’ for what turned out to be an absolutely wonderful (and much too short) stay at your Chatham cottage. We could not have asked for more. It was...
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Great Location! Great Views!

— Property 233892
Chatham house rental - Front of the House
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, near the ocean, town, air-conditioning
Rates - per property (USD)
$225 - $275/night
$1,500 - $2,500/week
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Totally Renovated 3 bedroom 2 full bath Home in Chatham

— Property 158527
Chatham house rental - Front of the House
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, town, air-conditioning
Rates - per property (USD)
$150 - $250/night
$1,250 - $2,000/week