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Vacation Rentals in Chatham, Massachusetts

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about Chatham

Chatham, Massachusetts Vacation Rentals and Tourism

Keep up with the Joneses and take your next vacation to Cape Cod. Book one of our cheap but posh Chatham, MA rentals today. Chatham vacation rentals are available for travelers looking to travel to Massachusetts on their next trip. Although it’s a popular summer destination, Chatham Cape Cod is fun any time of year; travel during off-season and enjoy privacy from the throngs of tourists and college “Junebugs.”

When you rent a Chatham cottage or condo, you can blend into the Cape Cod way of life. Why spend money to camp out in a hotel room or pay an arm and a leg in a seaside resort? With Chatham rentals, you’ll enjoy sleeping on high quality sheets, waking up to coffee on your private patio, and watching movies on a home theater system. Anglers will appreciate the convenience of being able to grill what they catch in their own kitchen – also a great way to save money! As an added plus, Chatham lodging can be found all over Cape Cod, including alongside fishing piers.

Chatham condos and homes are a paradox of laid back elegance. Spend the day at the beach or explore the charming town by foot. Places to include on your agenda: Monomoy National Wildlife Refuge, Monomoy Theater, Atwood House, Chatham Railroad Museum, and the Old Grist Mill. Search for your Chatham rental today!

Also, don't forget to browse our guide to Chatham resorts.

Deals on Chatham MA Vacation Rentals

Whether you're looking for Chatham apartments or beach condos or villas, Vacation Rentals.com has a great deal for you. As far as Cape Cod goes, Chatham properties are some of the most charming! And fortunately, they're within your budget, too. With cozy but affordable Cape Cod rentals, Chatham becomes a reasonable vacation destination for budget-conscious families and just about any other traveler imaginable.

No matter what you plan to do in the area, make sure to quickly book one of our vacation rentals; Chatham summer accommodations go fast!

Situated next to Cape Cod, Chatham fishing and beautiful weather bring thousands of people here every year. In the summer, the population triples because cheap Chatham summer rentals are such wonderful places to stay. And when you book a Chatham discounted vacation rental you will be able to see why so many people come here. With our discounted rates on Chatham last minute deals you will save money and get the best value possible, which allows you to enjoy an affordable yet memorable vacation.

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Charming, Comfortable, Private Cape Cod Home
Chatham House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,300 - $2,000 /wk
 
 
 
 
 

12 reviews write a review

Oceanfront Beach Cottage / Spectacular Views
Chatham Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $170 - $300 /nt
    $950 - $3,100 /wk
 
 
 
 
 

29 reviews write a review

Island View Lane ( Special reduced 2014)
Chatham House Rental Picture
  • bedrooms 4
  • community Island View
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,500 - $3,500 /wk
 
 
 
 
 

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Lighthouse Beach - near Chatham Bars Inn - Shore Road
Chatham House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $550 - $1,300 /nt
    $2,900 - $7,900 /wk
 
 
 
 
 

2 reviews write a review

4 bedroom, 2 bath home
Chatham House Rental Picture
  • bedrooms 4
  • community Old Village
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,750 - $2,950 /wk
 
 
 
 
 

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Taylors Pond/Cockle Cove Beach/Chatham Bike Trail
Chatham House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,050 - $1,200 /wk
 
 
 
 
 

6 reviews write a review

Traditional Cape Cod Style Home
Chatham House Rental Picture
  • bedrooms 3
  • community Hardings Beach
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $1,000 - $1,500 /wk
 
 
 
 
 

1 reviews write a review

In town Victorian - updated and charming
Chatham House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $1,500 - $4,500 /wk
    $4,000 - $15,000 /mth
 
 
 
 
 

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'Four Winds' direct waterfront, private beach, Pleasant Bay
Chatham House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,000 - $5,800 /wk
 
 
 
 
 

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4BR-Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town!
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $180 - $410 /nt
    $1,260 - $2,870 /wk
 
 
 
 
 

10 reviews write a review

Chatham Cottage on Lake One Mile to Ocean Beaches
Chatham Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $136 - $160 /nt
    $850 - $950 /wk
 
 
 
 
 

5 reviews write a review

Cockle Creek and Tidal Salt Marsh View 6/10 mi to popular Ridgevale Beac
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $2,400 /wk
 
 
 
 
 

5 reviews write a review

Beautiful home w/ ocean view-133 seconds to sand! Ask about May/June deals!
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 13
  • baths 3
  • rates (USD) $495 - $999 /nt
    $2,995 - $6,995 /wk
    $24,995 /mth
 
 
 
 
 

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In-Town Location - Walking Distance to Everything
Chatham Estate Rental Picture
  • bedrooms 3
  • rental type Estate
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $286 - $343 /nt
    $2,400 /wk
    $7,000 - $8,600 /mth
 
 
 
 
 

4 reviews write a review

Chatham's Best Views with private family Beach, 4 Kayaks, Waterfront Splendor !
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $600 - $950 /nt
    $3,000 - $6,300 /wk
 
 
 
 
 

6 reviews write a review

Oceanfront Beach Cottage - Spectacular Views
Chatham Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD)
 
 
 
 
 

29 reviews write a review

Fabulous water views!
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $500 - $857 /nt
    $3,000 - $6,000 /wk
 
 
 
 
 

9 reviews write a review

Completely Remodeled 4 bedroom 2 Bath
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $275 - $300 /nt
    $1,400 - $2,100 /wk
 
 
 
 
 

6 reviews write a review

Wildlife Lovers Salt Pond Perch- The Pondhouse- An Authentic Cape Cod Experience
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,100 - $2,200 /wk
 
 
 
 
 

2 reviews write a review

Inviting Home Near Ridgevale Beach - Family Friendly
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
 
 
 
 
 

2 reviews write a review

Book our Cape Cod, Chatham home: perfect for families
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $300 - $500 /nt
    $3,297 /wk
    $12,870 /mth
 
 
 
 
 

13 reviews write a review

Location, Location, Location!!! Walk To Beaches And Shops
Chatham Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 8
  • baths 2
  • rates (USD) $300 - $650 /nt
    $1,750 - $2,800 /wk
    $6,000 - $10,000 /mth
 
 
 
 
 

2 reviews write a review

4 Bedroom 2.5 Bath, Short Walk to Ridgevale Beach W/AC
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $3,500 /wk
 
 
 
 
 

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Windmill Overlooking Oyster Pond. Breathtaking Water Views
Chatham Mill Rental Picture
  • bedrooms 1
  • rental type Mill
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

14 reviews write a review

Sea Captains House Overlooking Oyster Pond in Chatham newly restored built 1801
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $550 - $986 /nt
    $3,800 - $6,900 /wk
 
 
 
 
 

9 reviews write a review

Carriage House with Water View, Short Walk to Town and Beach
Chatham Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 - $300 /nt
    $2,100 /wk
 
 
 
 
 

11 reviews write a review

Recently Renovated Chatham-Bayview Beach House--Central a/C
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

6 reviews write a review

Spacious Waterfront Summer Home With Direct Freshwater Lake Access
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $564 - $575 /nt
    $2,950 - $3,950 /wk
    $8,000 - $14,000 /mth
 
 
 
 
 

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Near Chatham Bars Inn / Lighhouse Beach / Oceanside
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $7,399 /wk
 
 
 
 
 

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Lighthouse Beach / Chatham Bars Inn / Shore Road / Oceanside
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $550 - $1,129 /nt
    $2,900 - $7,900 /wk
 
 
 
 
 

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5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $250 - $570 /nt
    $1,750 - $3,990 /wk
 
 
 
 
 

22 reviews write a review

Chatham - Stage Harbor-Walk to Town
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $4,495 - $8,995 /wk
 
 
 
 
 

12 reviews write a review

Chatham -Central Air - Walk to Popular Ridgevale Beach
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths 2
  • rates (USD) $1,495 - $2,995 /wk
 
 
 
 
 

18 reviews write a review

Close To Bike Path And South Chatham Beaches
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 0
  • rates (USD) $225 - $279 /nt
    $1,500 - $1,950 /wk
 
 
 
 
 

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Newly Renovated Private Setting at end of Cul-de-Sac 5' Walk to the Beach!
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 9
  • baths 2
  • rates (USD) $171 - $357 /nt
    $1,900 - $2,500 /wk
 
 
 
 
 

2 reviews write a review

Olde Chatham Village, Mill Pond, Custom Beach House
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

7 reviews write a review

In Town, Preservation Award, Sept. Oct. Great weather. Golf at Private Course.
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $214 - $414 /nt
    $1,500 - $2,900 /wk
 
 
 
 
 

5 reviews write a review

Great Beach Location
Chatham House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $200 - $264 /nt
    $1,050 - $1,850 /wk
 
 
 
 
 

2 reviews write a review

Slice of Old Cape Cod, 5BR, 4 Secluded Acres, Walk to Beach
Chatham Farmhouse Rental Picture
  • bedrooms 5
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD)
 
 
 
 
 

3 reviews write a review

Chatham Beach House at Ridgevale for Family Fun
Chatham House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $3,500 /wk
 
 
 
 
 

1 reviews write a review

Fabulous Location, Walk To Beach, Village, Shops, Restaurants,Backyard Sanctuary
Chatham House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 10
  • baths
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Chatham, Morris Island. Ocean Views. Private Beach.
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $800 - $1,214 /nt
    $4,900 - $8,500 /wk
    $32,000 /mth
 
 
 
 
 

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Chatham - Hardings and Ridgevale Beach location - Pottery Barn Decor
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $286 - $400 /nt
    $1,800 - $2,600 /wk
 
 
 
 
 

8 reviews write a review

*Chatham Classic Beautiful Water Views*
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $3,500 - $5,000 /wk
 
 
 
 
 

14 reviews write a review

North Chatham-Water View-Walk to Beach
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,495 - $2,995 /wk
 
 
 
 
 

14 reviews write a review

Chatham - Mill Pond - Stage Harbor-Water View
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths 4
  • rates (USD) $356 - $1,285 /nt
    $4,495 - $8,995 /wk
 
 
 
 
 

48 reviews write a review

Chatham Waterfront Compound -- 200' of Beach
Chatham Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • sleeps 12
  • baths 6
  • rates (USD) $2,071 - $2,357 /nt
    $16,500 /wk
 
 
 
 
 

5 reviews write a review

Premier*Chatham Harbor* 5A 7++BR Seaside Elegant Estate w Own Beach/Walk To Town
Chatham Estate Rental Picture
  • bedrooms 9
  • rental type Estate
  • owner badgeowner badge
  • sleeps 20
  • baths 5
  • rates (USD) $500 - $2,214 /nt
    $15,500 /wk
 
 
 
 
 

10 reviews write a review

600 steps to the beach !
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,600 - $3,000 /wk
 
 
 
 
 

2 reviews write a review

Spacious Salt Waterfront Home Sleeps 10; Ideal for Two Families with Dock
Chatham House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $5,500 - $7,000 /wk
 
 
 
 
 

4 reviews write a review

Think Sun, Surf and Sand - Walk to Nantucket Sound Beach
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,500 - $2,500 /wk
 
 
 
 
 

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Beautiful Chatham Cottage Walk To Town, Restaurants And Baseball Field
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,601 /wk
 
 
 
 
 

4 reviews write a review

Direct Ocean Front - Private Sandy Beach - 5 Min. Walk to Town
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 3
  • rates (USD) $6,930 - $10,900 /wk
    $27,720 /mth
 
 
 
 
 

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New - Renovated - Walk to Beach - Fully Loaded - Pottery Barn Style Home
Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,350 - $3,000 /wk
 
 
 
 
 

2 reviews write a review

Beachfront Nantucket style cottage with amazing views on 3 acre estate setting
Chatham Cottage Rental Picture
  • bedrooms 5
  • rental type Cottage
  • sleeps 8
  • baths
  • rates (USD) $400 - $975 /nt
    $2,800 - $5,450 /wk
    $11,000 - $21,000 /mth
 
 
 
 
 

3 reviews write a review