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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Great family vacation house Steps to Ridgevale Beach

— Property 242790
Chatham house rental - Front of House
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$1,600 - $2,500/week
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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 Dec 3 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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Gorgeous Home Near Nantucket Sound Beach

— Property 7035179h
Chatham house rental - Front
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, air-conditioning, antiquing
Rates - per house (USD)
$2,500/week
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Beautiful Waterviews Steps to Beach

— Property 7035178h
Chatham house rental - Front
4 Bedrooms, Sleeps 9,
House, 3 Bathrooms, adventure, air-conditioning
Rates - per house (USD)
$2,400 - $3,250/week
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Pleasant Bay: Bright and Airy Cape at Chatham / Harwich Line

— Property 188362
Chatham house rental - Classic Cape Cod near Pleasant Bay
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, near the ocean, internet access
Rates - per property (USD)
$1,775 - $2,775/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 Dec 2 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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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 Dec 3 2009

Property Review

Wonderful home and location! Everything you could possibly need in a rental.
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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 Dec 2 2009

Property Review

Great Cottage! Great Location! Great Vacation! What else could you ask for.......................
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281 Deer Meadow Ln

— Property 7022224h
Chatham house rental
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, adventure, air-conditioning
Rates - per house (USD)
$1,600/week
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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 30 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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'Chatham Breeze' - That's what we call it!

— Property 208441
Chatham house rental - Entering Your Chatham Vacation Home
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, downtown, near the ocean, garden
Rates - per property (USD)
$2,500 - $3,000/week
Calendar Updated Dec 2 2009

Property Review

Our family just can't say enough about "Chatham Breeze", the house we rented in Cape Cod at the end of August '09. The house was just "sparkling" when we arrived for our week vacation. The rooms...
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Classic North Chatham Escape

— Property 7035484h
Chatham house rental
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per house (USD)
$2,100 - $2,700/week
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Large, pristine Chatham home, private tennis court, walk to beach and Town.

— Property 7035487h
Chatham house rental
5 Bedrooms, Sleeps 8,
House, 4 Bathrooms, adventure, bird watching
Rates - per house (USD)
$8,000/week
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North Chatham home offers space, cleanliness and value in a great location

— Property 7035498h
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, adventure, clothes dryer
Rates - per house (USD)
$1,700 - $2,500/week
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Pristine Morris Island Road Home in Chatham

— Property 7035501h
Chatham house rental
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per house (USD)
$4,200 - $5,200/week
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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 30 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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New Luxury Home/Walk to Town/Beach

— Property 186347
Chatham house rental - Front view of house
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, beach, downtown, garden
Calendar Updated Nov 30 2009

Property Review

Our family of five, plus a 9-month-old, stayed at this beautiful property for a week in June. Everything was in excellent condition and it offered enough space for us to spread out and be...
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Private Contemporary Cape Set on a Hilltop

— Property 121479
Chatham house rental - Contemporary Cape - Comfortable and Private
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$1,400 - $1,900/week
Calendar Updated Nov 30 2009

Property Review

The pictures of this house do not do it justice. It is absolutely beautiful. Only minutes to beaches and downtown Chatham. We stayed for a week and it was wonderful Michele
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Charming cape with gorgeous sunroom close to beaches and Chatham Center

— Property 249437
Chatham house rental - Third bedroom on main floor - queen bed
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the ocean, town, garden
Rates - per property (USD)
$1,900/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, balcony
Rates - per property (USD)
$2,500 - $7,995/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 29 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 29 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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Private Beach, Top Neighborhood, Lovely Cape

— Property 156662
Chatham house rental - Property exterior
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, beach, near the ocean, terrace
Rates - per property (USD)
$4,000/week
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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 Dec 1 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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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 Dec 1 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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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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Chatham house rental - High Tide
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, waterfront, garden
Rates - per property (USD)
$2,150/week
Calendar Updated Nov 25 2009

Property Review

Dear Chris, Thank you for your email. We had a wonderful time at The Pondhouse. We appreciated the layout of the house with the living room and dining room looking out over the deck and pond...
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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