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Holiday Rentals in Chatham

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Bathrooms

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5 km
487 rentals in Chatham.
Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, holiday rental in Chatham

Fully Updated Chatham Cottage Near Hardings Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chatham walk to Cape Cod beach, holiday rental in Chatham
Chatham walk to Cape Cod beach, holiday rental in Chatham
Chatham walk to Cape Cod beach, holiday rental in Chatham

Chatham walk to Cape Cod beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham

Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, holiday rental in Chatham

Clean, Bright, and Spacious; Family Friendly!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, holiday rental in Chatham

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, holiday rental in Chatham

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, holiday rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, holiday rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, holiday rental in Chatham

Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor, holiday rental in Chatham

SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Cape House Walking Distance to the Beach, holiday rental in Chatham
Classic Cape House Walking Distance to the Beach, holiday rental in Chatham
Classic Cape House Walking Distance to the Beach, holiday rental in Chatham

Classic Cape House Walking Distance to the Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, holiday rental in Chatham

Steps to Chatham Center & Lighthouse Beach - charming home with central AC

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., holiday rental in Chatham

5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more...

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, holiday rental in Chatham

Harwich Retreat, Private Pool, Beach nearby, Family Home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., holiday rental in Chatham

Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full Renovation! Amazing Spot with Views!, holiday rental in Chatham
Full Renovation! Amazing Spot with Views!, holiday rental in Chatham
Full Renovation! Amazing Spot with Views!, holiday rental in Chatham

Full Renovation! Amazing Spot with Views!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham
Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham
Chatham 3 Bedroom/2 Bath Retreat, holiday rental in Chatham

Chatham 3 Bedroom/2 Bath Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique opportunity just opened up - July 5-13. Oyster Pond close to town, holiday rental in Chatham
Unique opportunity just opened up - July 5-13. Oyster Pond close to town, holiday rental in Chatham
Unique opportunity just opened up - July 5-13. Oyster Pond close to town, holiday rental in Chatham

Unique opportunity just opened up - July 5-13. Oyster Pond close to town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, holiday rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, holiday rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., holiday rental in Chatham
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., holiday rental in Chatham
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., holiday rental in Chatham

BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, holiday rental in Chatham
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, holiday rental in Chatham
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Close to Bike Path 1 Mile to Beaches!, holiday rental in Chatham
Close to Bike Path 1 Mile to Beaches!, holiday rental in Chatham
Close to Bike Path 1 Mile to Beaches!, holiday rental in Chatham

Close to Bike Path 1 Mile to Beaches!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, holiday rental in Chatham
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, holiday rental in Chatham
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, holiday rental in Chatham

Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Chatham Town Home.  Close to town & beaches!, holiday rental in Chatham
Luxury Chatham Town Home.  Close to town & beaches!, holiday rental in Chatham
Luxury Chatham Town Home.  Close to town & beaches!, holiday rental in Chatham

Luxury Chatham Town Home. Close to town & beaches!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fully Updated Home w/ Great Outdoor Space!, holiday rental in Chatham
Fully Updated Home w/ Great Outdoor Space!, holiday rental in Chatham
Fully Updated Home w/ Great Outdoor Space!, holiday rental in Chatham

Fully Updated Home w/ Great Outdoor Space!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern, RENOVATED, 3-bed PeachTree House, holiday rental in Chatham
Modern, RENOVATED, 3-bed PeachTree House, holiday rental in Chatham
Modern, RENOVATED, 3-bed PeachTree House, holiday rental in Chatham

Modern, RENOVATED, 3-bed PeachTree House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Game Room Rooftop Deck Fire Pit!!, holiday rental in Chatham
Game Room Rooftop Deck Fire Pit!!, holiday rental in Chatham
Game Room Rooftop Deck Fire Pit!!, holiday rental in Chatham

Game Room Rooftop Deck Fire Pit!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Steps to Oyster Pond Private Dock!, holiday rental in Chatham
Steps to Oyster Pond Private Dock!, holiday rental in Chatham
Steps to Oyster Pond Private Dock!, holiday rental in Chatham

Steps to Oyster Pond Private Dock!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs, holiday rental in Chatham
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs, holiday rental in Chatham
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs, holiday rental in Chatham

Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Centrally Located Beach Home, holiday rental in Chatham
Centrally Located Beach Home, holiday rental in Chatham
Centrally Located Beach Home, holiday rental in Chatham

Centrally Located Beach Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, holiday rental in Chatham
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, holiday rental in Chatham
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, holiday rental in Chatham

Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, holiday rental in Chatham
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, holiday rental in Chatham
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, holiday rental in Chatham

Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, holiday rental in Chatham
Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, holiday rental in Chatham
Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, holiday rental in Chatham

Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, holiday rental in Chatham
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, holiday rental in Chatham
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, holiday rental in Chatham

Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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This lovely condo location in town, has both a brick patio and deck for you to, holiday rental in Chatham
This lovely condo location in town, has both a brick patio and deck for you to, holiday rental in Chatham
This lovely condo location in town, has both a brick patio and deck for you to, holiday rental in Chatham

This lovely condo location in town, has both a brick patio and deck for you to

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Inviting apartment with patio, full kitchen, & golf nearby, holiday rental in Chatham
Inviting apartment with patio, full kitchen, & golf nearby, holiday rental in Chatham
Inviting apartment with patio, full kitchen, & golf nearby, holiday rental in Chatham

Inviting apartment with patio, full kitchen, & golf nearby

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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1/4 MILE TO BEAUTIFUL RIDGEVALE BEACH.....AND PET FRIENDLY!!, holiday rental in Chatham
1/4 MILE TO BEAUTIFUL RIDGEVALE BEACH.....AND PET FRIENDLY!!, holiday rental in Chatham
1/4 MILE TO BEAUTIFUL RIDGEVALE BEACH.....AND PET FRIENDLY!!, holiday rental in Chatham

1/4 MILE TO BEAUTIFUL RIDGEVALE BEACH.....AND PET FRIENDLY!!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Perfect couples escape. Close to beaches, great biking & walking & pet friendly., holiday rental in Chatham
Perfect couples escape. Close to beaches, great biking & walking & pet friendly., holiday rental in Chatham
Perfect couples escape. Close to beaches, great biking & walking & pet friendly., holiday rental in Chatham

Perfect couples escape. Close to beaches, great biking & walking & pet friendly.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sophisticated decor with an amazing use of space throughout this two bedroom (1, holiday rental in Chatham
Sophisticated decor with an amazing use of space throughout this two bedroom (1, holiday rental in Chatham
Sophisticated decor with an amazing use of space throughout this two bedroom (1, holiday rental in Chatham

Sophisticated decor with an amazing use of space throughout this two bedroom (1

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, holiday rental in Chatham
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, holiday rental in Chatham
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, holiday rental in Chatham

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, holiday rental in Chatham
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, holiday rental in Chatham
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, holiday rental in Chatham

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, holiday rental in Chatham
Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, holiday rental in Chatham
Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, holiday rental in Chatham

Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Chatham Cottage, holiday rental in Chatham
Charming Chatham Cottage, holiday rental in Chatham
Charming Chatham Cottage, holiday rental in Chatham

Charming Chatham Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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This clean and adorable two bedroom, 1 1/2 bath cottage is the perfect vacation, holiday rental in Chatham
This clean and adorable two bedroom, 1 1/2 bath cottage is the perfect vacation, holiday rental in Chatham
This clean and adorable two bedroom, 1 1/2 bath cottage is the perfect vacation, holiday rental in Chatham

This clean and adorable two bedroom, 1 1/2 bath cottage is the perfect vacation

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Wonderful cottage located in the heart of downtown Chatham......steps to, holiday rental in Chatham
Wonderful cottage located in the heart of downtown Chatham......steps to, holiday rental in Chatham
Wonderful cottage located in the heart of downtown Chatham......steps to, holiday rental in Chatham

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Home with Water Views!, holiday rental in Chatham
Stunning Home with Water Views!, holiday rental in Chatham
Stunning Home with Water Views!, holiday rental in Chatham

Stunning Home with Water Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming/Great Location/Walk to town/baseball field, holiday rental in Chatham
Charming/Great Location/Walk to town/baseball field, holiday rental in Chatham
Charming/Great Location/Walk to town/baseball field, holiday rental in Chatham

Charming/Great Location/Walk to town/baseball field

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, holiday rental in Chatham
Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, holiday rental in Chatham
Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, holiday rental in Chatham

Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quaint 2 bedroom home on quiet street., holiday rental in Chatham
Quaint 2 bedroom home on quiet street., holiday rental in Chatham
Quaint 2 bedroom home on quiet street., holiday rental in Chatham

Quaint 2 bedroom home on quiet street.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!, holiday rental in Chatham
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!, holiday rental in Chatham
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!, holiday rental in Chatham

Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Wrap-Around Porch Mins. to Beach!, holiday rental in Chatham
Wrap-Around Porch Mins. to Beach!, holiday rental in Chatham
Wrap-Around Porch Mins. to Beach!, holiday rental in Chatham

Wrap-Around Porch Mins. to Beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 487
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