Chatham Vacation Rentals - Chatham, Massachusetts Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

On the Chatham Loop - 1 Min to the Beach!

On the Chatham Loop - 1 Min to the Beach!

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Chatham Massachusetts Private vacation home From $308 per night (USD)

Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel

Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel

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Chatham Massachusetts Private vacation home From $575 per night (USD)

$Chatham-Walk to Town\/Beach-Multi Family Friendly$

Chatham-Walk to Town\/Beach-Multi Family Friendly

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Chatham Massachusetts Private vacation home From $611 per night (USD)

Chatham Village - Adorable Studio Apartment in Antique Home

Chatham Village - Adorable Studio Apartment in Antique Home

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Chatham Massachusetts Apartment Click For Pricing

1 Mile from Downtown Chatham Walk to Pier

1 Mile from Downtown Chatham Walk to Pier

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Chatham Massachusetts Private vacation home From $247 per night (USD)

Newly updated home sleeps 7, AC, free WIFI, half mile to town

Newly updated home sleeps 7, AC, free WIFI, half mile to town

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Chatham Massachusetts Private vacation home From $768 per night (USD)

$Dog-Friendly Home w\/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach$

Dog-Friendly Home w\/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach

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Chatham Massachusetts Private vacation home From $131 per night (USD)

$Pond Front Home w\/ Game Room Dog Friendly!$

Pond Front Home w\/ Game Room Dog Friendly!

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Chatham Massachusetts Private vacation home From $324 per night (USD)

$Perfect for Group w\/ Kids & Dogs w\/ Hot Tub$

Perfect for Group w\/ Kids & Dogs w\/ Hot Tub

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Chatham Massachusetts Private vacation home From $376 per night (USD)

GREAT LOCATION - Water View, Walk to beach & Town!

GREAT LOCATION - Water View, Walk to beach & Town!

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Chatham Massachusetts Private vacation home From $716 per night (USD)

4 Bedrooms, 2 Baths, Sleeps 8

4 Bedrooms, 2 Baths, Sleeps 8

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Chatham Massachusetts Private vacation home From $550 per night (USD)

Fantastically located Chatham house - DISCOUNTED - New patio, refurbished

Fantastically located Chatham house - DISCOUNTED - New patio, refurbished

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Chatham Massachusetts Private vacation home From $752 per night (USD)

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

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Chatham Massachusetts Apartment Click For Pricing

Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!

Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!

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West Chatham Massachusetts Private vacation home From $757 per night (USD)

Steps to Oyster Pond Private Dock!

Steps to Oyster Pond Private Dock!

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Chatham Massachusetts Private vacation home From $1139 per night (USD)

Chatham Beach Chic 5 ⭐ 5min's Walk to Private Beach-Newly Renov'd Family Retreat

Chatham Beach Chic 5 ⭐ 5min's Walk to Private Beach-Newly Renov'd Family Retreat

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Chatham Massachusetts Private vacation home From $495 per night (USD)

Chatham Village - Lovely 2 bedroom apartment in the antique home

Chatham Village - Lovely 2 bedroom apartment in the antique home

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Chatham Massachusetts Apartment Click For Pricing

Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides.

Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides.

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Chatham Massachusetts Private vacation home Click For Pricing

Blue water views and coral sunsets from every room in this beautifully appointed home.

Blue water views and coral sunsets from every room in this beautifully appointed home.

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Chatham Massachusetts Private vacation home From $771 per night (USD)

This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!

This lovely condo location in town, has both a brick patio and deck for you to enjoy your morning coffee on!

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Chatham Massachusetts Condo From $207 per night (USD)

Tennis anyone? Beautiful, brand new construction with 8 bedrooms, 8 full baths and 2 half baths, that can sleep up to 20 guests.

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Chatham Massachusetts Private vacation home From $1478 per night (USD)

Pet friendly and waterfront!

Pet friendly and waterfront!

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Chatham Massachusetts Private vacation home From $400 per night (USD)

Quaint 2 bedroom home on quiet street.

Quaint 2 bedroom home on quiet street.

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Chatham Massachusetts Private vacation home From $264 per night (USD)

School Street in the Old Village!! Charming, new construction with attention to detail!

School Street in the Old Village!! Charming, new construction with attention to detail!

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Chatham Massachusetts Private vacation home From $936 per night (USD)

Charming house located in the heart of downtown Chatham!

Charming house located in the heart of downtown Chatham!

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Chatham Massachusetts Private vacation home From $425 per night (USD)

Pet Friendly in Riverbay! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay.

Pet Friendly in Riverbay! Nicely furnished 3 bedroom, 2 full bath home in quiet Riverbay.

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Chatham Massachusetts Private vacation home From $354 per night (USD)

It's all about the location and charm! Located in the heart of Chatham's Old Village and boasting a beautiful marsh view.

It's all about the location and charm! Located in the heart of Chatham's Old Village and boasting a beautiful marsh view.

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Chatham Massachusetts Private vacation home From $614 per night (USD)

5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home

5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home

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Chatham Massachusetts Private vacation home From $550 per night (USD)

Chatham Village: Charming 3 Room Apartment in Antique Home

Chatham Village: Charming 3 Room Apartment in Antique Home

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Chatham Massachusetts Apartment Click For Pricing

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

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Chatham Massachusetts Private vacation home From $163 per night (USD)

Pet Friendly on Oyster Pond River!

Pet Friendly on Oyster Pond River!

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Chatham Massachusetts Private vacation home From $438 per night (USD)

Quiet, Luxury Retreat Surrounded by Serene Gardens and Landscaping - Free WiFi

Quiet, Luxury Retreat Surrounded by Serene Gardens and Landscaping - Free WiFi

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Chatham Massachusetts Apartment Click For Pricing

Cozy and Conveniently located near the bike path!

Cozy and Conveniently located near the bike path!

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Chatham Massachusetts Private vacation home From $315 per night (USD)

$Stunning Home w\/ Incredible Water Views!$

Stunning Home w\/ Incredible Water Views!

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North Chatham Massachusetts Private vacation home From $419 per night (USD)

$Spacious 3 BR w\/A C | Walk to the Beach | Quintessential Cape Cod$

Spacious 3 BR w\/A C | Walk to the Beach | Quintessential Cape Cod

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South Chatham Massachusetts Private vacation home From $500 per night (USD)

Lovely Updated Cape Home 1 Mile to Beach!

Lovely Updated Cape Home 1 Mile to Beach!

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Chatham Massachusetts Private vacation home From $455 per night (USD)

Wonderful cottage located in the heart of downtown Chatham......steps to everything.

Wonderful cottage located in the heart of downtown Chatham......steps to everything.

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Chatham Massachusetts Cottage From $345 per night (USD)

Walk to private beach, central air, wifi, 3 bedrooms.

Walk to private beach, central air, wifi, 3 bedrooms.

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Chatham Ma Cottage From $429 per night (USD)

Stylish coastal getaway with dual living areas - walk to Main Street, near beach

Stylish coastal getaway with dual living areas - walk to Main Street, near beach

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Chatham Massachusetts Private vacation home From $413 per night (USD)

$Sunny Updated Chatham Village 2 Bedroom Condo W\/ Large Private Deck$

Sunny Updated Chatham Village 2 Bedroom Condo W\/ Large Private Deck

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Chatham Massachusetts Condo From $378 per night (USD)

$Beautiful, cozy ranch home w\/ a deck - walking distance to Downtown Chatham$

Beautiful, cozy ranch home w\/ a deck - walking distance to Downtown Chatham

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Chatham Massachusetts Private vacation home Click For Pricing

Updated Chatham Inn Home | Spacious Deck & Private Heated Pool

Updated Chatham Inn Home | Spacious Deck & Private Heated Pool

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Chatham Massachusetts Private vacation home From $484 per night (USD)

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

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Chatham Massachusetts Condo From $165 per night (USD)

Waterfront house on Bucks Creek Marsh with deck, dock, & kayaks

Waterfront house on Bucks Creek Marsh with deck, dock, & kayaks

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Chatham Massachusetts Private vacation home From $582 per night (USD)

Beachfront on Pleasant Bay!!

Beachfront on Pleasant Bay!!

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North Chatham Massachusetts Private vacation home From $1480 per night (USD)

Step back in time in this beautifully maintained antique horse barn cottage!!

Step back in time in this beautifully maintained antique horse barn cottage!!

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Chatham Massachusetts Private vacation home From $236 per night (USD)

Sweet clapboard cottage that is walk to the beach and downtown!

Sweet clapboard cottage that is walk to the beach and downtown!

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Chatham Massachusetts Cottage From $171 per night (USD)

PRIVATE HEATED POOL! Pet friendly, sleeps 9 near the beach!

PRIVATE HEATED POOL! Pet friendly, sleeps 9 near the beach!

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West Chatham Massachusetts Private vacation home From $1405 per night (USD)

Cute clapboard cottage on the hill off Stage Island Road!

Cute clapboard cottage on the hill off Stage Island Road!

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Chatham Massachusetts Cottage From $171 per night (USD)

Colorful clapboard cottage perfect for 2!

Colorful clapboard cottage perfect for 2!

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Chatham Massachusetts Cottage From $129 per night (USD)

Just off the Chatham bike loop... a perfect location for your family vacation.

Just off the Chatham bike loop... a perfect location for your family vacation.

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Chatham Massachusetts Private vacation home From $357 per night (USD)

5-Mins to Forest Beach Dog Friendly!

5-Mins to Forest Beach Dog Friendly!

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South Chatham Massachusetts Private vacation home From $529 per night (USD)

Newly Renovated Modern Pond Access!

Newly Renovated Modern Pond Access!

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South Chatham Massachusetts Private vacation home From $424 per night (USD)

Wrap-Around Porch Mins. to Beach!

Wrap-Around Porch Mins. to Beach!

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South Chatham Massachusetts Private vacation home From $207 per night (USD)

The Boarding House, Air conditioned King bed comfort

The Boarding House, Air conditioned King bed comfort

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Chatham Massachusetts Private vacation home From $466 per night (USD)

Chatham Home ~1 Mi to Downtown & Oyster Pond Beach

Chatham Home ~1 Mi to Downtown & Oyster Pond Beach

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Chatham Massachusetts Private vacation home From $382 per night (USD)

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

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Chatham Massachusetts Private vacation home From $700 per night (USD)

5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!

5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!

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Chatham Massachusetts Private vacation home From $350 per night (USD)

$Walk to Beach-Water views-Central A\/C and WiFi$

Walk to Beach-Water views-Central A\/C and WiFi

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South Chatham Massachusetts Private vacation home From $654 per night (USD)

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

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Chatham Massachusetts Cottage From $396 per night (USD)

Spacious Home on the Loop in Chatham

Spacious Home on the Loop in Chatham

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Chatham Massachusetts Private vacation home From $650 per night (USD)

$Cape Cod House w\/ Deck & Grill: 2 Mi to Beach!$

Cape Cod House w\/ Deck & Grill: 2 Mi to Beach!

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South Chatham Massachusetts Private vacation home From $245 per night (USD)

Deeded Rights to Emery Pond Fire Pit!

Deeded Rights to Emery Pond Fire Pit!

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Chatham Massachusetts Private vacation home From $202 per night (USD)

Full Renovation! Amazing Spot with Views!

Full Renovation! Amazing Spot with Views!

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Chatham Massachusetts Condo From $393 per night (USD)

Spacious home in quiet neighborhood!

Spacious home in quiet neighborhood!

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Chatham Massachusetts Private vacation home From $457 per night (USD)

$Beautiful Home w\/ Artistic Flair!$

Beautiful Home w\/ Artistic Flair!

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Chatham Massachusetts Private vacation home From $359 per night (USD)

$Centrally Located Home w\/ Patio Fire Pit!$

Centrally Located Home w\/ Patio Fire Pit!

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Chatham Massachusetts Private vacation home From $613 per night (USD)

North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place

North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place

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North Chatham Massachusetts Private vacation home From $400 per night (USD)

Bungalow style home in downtown Chatham!

Bungalow style home in downtown Chatham!

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Chatham Massachusetts Private vacation home From $771 per night (USD)

Location and Luxury

Location and Luxury

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Chatham Massachusetts Private vacation home From $998 per night (USD)

9-Min Walk to Water Fire Pit!

9-Min Walk to Water Fire Pit!

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South Chatham Massachusetts Private vacation home From $373 per night (USD)

Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches

Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches

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South Chatham Massachusetts Private vacation home From $147 per night (USD)

Chatham Walk to Beach Cape Cod

Chatham Walk to Beach Cape Cod

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Chatham Massachusetts Private vacation home From $400 per night (USD)

Charming Downtown Chatham

Charming Downtown Chatham

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Chatham Massachusetts Condo From $257 per night (USD)

$Chatham 3 Bedroom\/2 Bath Retreat$

Chatham 3 Bedroom\/2 Bath Retreat

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Chatham Massachusetts Private vacation home From $357 per night (USD)

$\Chatham Up\ - Come Stay, Relax, Have Fun!$

\"Chatham Up\" - Come Stay, Relax, Have Fun!

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Chatham Massachusetts Private vacation home From $334 per night (USD)

CHARMING COASTAL COTTAGE IN NORTH CHATHAM.

CHARMING COASTAL COTTAGE IN NORTH CHATHAM.

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Chatham Massachusetts Private vacation home From $750 per night (USD)

Beachfront, ocean view, pet friendly, sleeps 8 Nauset Watch

Beachfront, ocean view, pet friendly, sleeps 8 Nauset Watch

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North Chatham Massachusetts Private vacation home Click For Pricing

$Dog-friendly waterfront home near downtown Chatham with fast WiFi & W\/D$

Dog-friendly waterfront home near downtown Chatham with fast WiFi & W\/D

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Chatham Massachusetts Private vacation home Click For Pricing

Cozy Cape near Chatham Center

Cozy Cape near Chatham Center

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Chatham Massachusetts Private vacation home From $379 per night (USD)

Air Conditioned, King bed Comfort .Dog friendly

Air Conditioned, King bed Comfort .Dog friendly

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Chatham Massachusetts Private vacation home From $374 per night (USD)

Stylishly Furnished Home- Access to Pleasant Street Beach

Stylishly Furnished Home- Access to Pleasant Street Beach

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Chatham Massachusetts Private vacation home From $440 per night (USD)

Amazing Location! Lakefront Waterside Deck

Amazing Location! Lakefront Waterside Deck

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Chatham Massachusetts Private vacation home From $419 per night (USD)

Sea Mist Lane, Chatham - Spectacular endless ocean views and amazing sunsets!

Sea Mist Lane, Chatham - Spectacular endless ocean views and amazing sunsets!

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South Chatham Massachusetts Private vacation home From $857 per night (USD)

Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!

Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!

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Chatham Massachusetts Private vacation home From $1113 per night (USD)

Charming Updated Home in Chatham!

Charming Updated Home in Chatham!

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South Chatham Massachusetts Private vacation home From $241 per night (USD)

$Quaint Chatham home w\/beautiful backyard & furnished multi-level deck, dogs OK$

Quaint Chatham home w\/beautiful backyard & furnished multi-level deck, dogs OK

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Chatham Massachusetts Private vacation home From $92 per night (USD)

WALK TO RESTAURANTS, SHOPS & LIQUOR STORE - CLOSE TO DOWNTOWN CHATHAM!!

WALK TO RESTAURANTS, SHOPS & LIQUOR STORE - CLOSE TO DOWNTOWN CHATHAM!!

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Chatham Massachusetts Cottage From $212 per night (USD)

$Cape Cod Home w\/ Fire Pit & Grill - Near Beaches!$

Cape Cod Home w\/ Fire Pit & Grill - Near Beaches!

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South Chatham Massachusetts Private vacation home From $429 per night (USD)

Walk to town, playground and the beach!

Walk to town, playground and the beach!

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Chatham Massachusetts Private vacation home From $427 per night (USD)

Water Views in Chatham!

Water Views in Chatham!

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Chatham Massachusetts Private vacation home From $748 per night (USD)

Located in the heart of downtown Chatham, this gem offers an easy walk to everything.

Located in the heart of downtown Chatham, this gem offers an easy walk to everything.

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Chatham Massachusetts Private vacation home From $471 per night (USD)

Dog friendly! Enjoy outdoor space with large yard, patio, and enclosed outdoor shower!

Dog friendly! Enjoy outdoor space with large yard, patio, and enclosed outdoor shower!

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Chatham Massachusetts Private vacation home From $429 per night (USD)

Off the Chatham Loop! Perfectly decorated rental home for comfort & family enjoyment.

Off the Chatham Loop! Perfectly decorated rental home for comfort & family enjoyment.

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Chatham Massachusetts Private vacation home Click For Pricing

Waterfront on Private Lake!

Waterfront on Private Lake!

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Chatham Massachusetts Private vacation home From $305 per night (USD)

$Water View-Walk town\/beach, pets considered, Linen Option$

Water View-Walk town\/beach, pets considered, Linen Option

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Chatham Ma Private vacation home From $777 per night (USD)

Charming Chatham Home Close to Bassing Harbor!

Charming Chatham Home Close to Bassing Harbor!

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North Chatham Massachusetts Private vacation home From $660 per night (USD)

Main Street in Chatham!

Main Street in Chatham!

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Chatham Massachusetts Private vacation home From $1000 per night (USD)

Pet friendly and quiet neighborhood.

Pet friendly and quiet neighborhood.

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North Chatham Massachusetts Private vacation home From $607 per night (USD)

Location, Location, Location!

Location, Location, Location!

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South Chatham Massachusetts Private vacation home From $550 per night (USD)

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