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Chatham Family & Kid Friendly Rentals

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5 mi
469 rentals in Chatham.
Fully Updated Chatham Cottage Near Hardings Beach, vacation rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, vacation rental in Chatham
Fully Updated Chatham Cottage Near Hardings Beach, vacation rental in Chatham

Fully Updated Chatham Cottage Near Hardings Beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Chatham walk to Cape Cod beach, vacation rental in Chatham
Chatham walk to Cape Cod beach, vacation rental in Chatham
Chatham walk to Cape Cod beach, vacation rental in Chatham

Chatham walk to Cape Cod beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham
Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham
Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham

Discounted Summer prices! Book now! WATERVIEWS! 4min drive to Hardings Beach!

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, Kid friendly
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Clean, Bright, and Spacious; Family Friendly!, vacation rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, vacation rental in Chatham
Clean, Bright, and Spacious; Family Friendly!, vacation rental in Chatham

Clean, Bright, and Spacious; Family Friendly!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, vacation rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, vacation rental in Chatham
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach, vacation 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, Kid friendly
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Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, vacation rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, vacation rental in Chatham
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit, vacation rental in Chatham

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, vacation rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, vacation rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach, vacation rental in Chatham

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

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

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Classic Cape House Walking Distance to the Beach, vacation rental in Chatham
Classic Cape House Walking Distance to the Beach, vacation rental in Chatham
Classic Cape House Walking Distance to the Beach, vacation rental in Chatham

Classic Cape House Walking Distance to the Beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Steps to Chatham Center & Lighthouse Beach - charming home with central AC, vacation rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, vacation rental in Chatham
Steps to Chatham Center & Lighthouse Beach - charming home with central AC, vacation rental in Chatham

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., vacation rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., vacation rental in Chatham
5 Bed/2 Bath Sleeps 11. Walk to restaurants, town and more..., vacation rental in Chatham

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, Kid friendly
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Harwich Retreat, Private Pool, Beach nearby, Family Home, vacation rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, vacation rental in Chatham
Harwich Retreat, Private Pool, Beach nearby, Family Home, vacation rental in Chatham

Harwich Retreat, Private Pool, Beach nearby, Family Home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., vacation rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., vacation rental in Chatham
Chillin' In Chatham, 5 minute Walk to Ridgevale Beach, Central Air, Sleeps 6., vacation rental in Chatham

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Full Renovation! Amazing Spot with Views!, vacation rental in Chatham
Full Renovation! Amazing Spot with Views!, vacation rental in Chatham
Full Renovation! Amazing Spot with Views!, vacation rental in Chatham

Full Renovation! Amazing Spot with Views!

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

Chatham 3 Bedroom/2 Bath Retreat

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

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, vacation rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, vacation rental in Chatham
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!, vacation rental in Chatham

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., vacation rental in Chatham
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., vacation rental in Chatham
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort., vacation rental in Chatham

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Exquisite Cottage - Minutes to Village Center and Beaches, vacation rental in Chatham
Exquisite Cottage - Minutes to Village Center and Beaches, vacation rental in Chatham
Exquisite Cottage - Minutes to Village Center and Beaches, vacation rental in Chatham

Exquisite Cottage - Minutes to Village Center and Beaches

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, vacation rental in Chatham
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, vacation rental in Chatham
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, vacation rental in Chatham

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Close to Bike Path 1 Mile to Beaches!, vacation rental in Chatham
Close to Bike Path 1 Mile to Beaches!, vacation rental in Chatham
Close to Bike Path 1 Mile to Beaches!, vacation rental in Chatham

Close to Bike Path 1 Mile to Beaches!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, vacation rental in Chatham
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, vacation rental in Chatham
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham, vacation rental in Chatham

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

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

Luxury Chatham Town Home. Close to town & beaches!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Fully Updated Home w/ Great Outdoor Space!, vacation rental in Chatham
Fully Updated Home w/ Great Outdoor Space!, vacation rental in Chatham
Fully Updated Home w/ Great Outdoor Space!, vacation rental in Chatham

Fully Updated Home w/ Great Outdoor Space!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Modern, RENOVATED, 3-bed PeachTree House, vacation rental in Chatham
Modern, RENOVATED, 3-bed PeachTree House, vacation rental in Chatham
Modern, RENOVATED, 3-bed PeachTree House, vacation rental in Chatham

Modern, RENOVATED, 3-bed PeachTree House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Game Room Rooftop Deck Fire Pit!!, vacation rental in Chatham
Game Room Rooftop Deck Fire Pit!!, vacation rental in Chatham
Game Room Rooftop Deck Fire Pit!!, vacation rental in Chatham

Game Room Rooftop Deck Fire Pit!!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Steps to Oyster Pond Private Dock!, vacation rental in Chatham
Steps to Oyster Pond Private Dock!, vacation rental in Chatham
Steps to Oyster Pond Private Dock!, vacation rental in Chatham

Steps to Oyster Pond Private Dock!

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

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

Rental Home
3 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Centrally Located Beach Home, vacation rental in Chatham
Centrally Located Beach Home, vacation rental in Chatham
Centrally Located Beach Home, vacation rental in Chatham

Centrally Located Beach Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, vacation rental in Chatham
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, vacation rental in Chatham
Exquisite Chatham Home, Easy Access to Town, Bike Trail: 330-C, vacation rental in Chatham

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, vacation rental in Chatham
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, vacation rental in Chatham
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling, vacation rental in Chatham

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, vacation rental in Chatham
Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, vacation rental in Chatham
Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC, vacation rental in Chatham

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

Rental Home
7 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps, Kid friendly
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Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, vacation rental in Chatham
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, vacation rental in Chatham
Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated: 021-C, vacation rental in Chatham

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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This lovely condo location in town, has both a brick patio and deck for you to, vacation rental in Chatham
This lovely condo location in town, has both a brick patio and deck for you to, vacation rental in Chatham
This lovely condo location in town, has both a brick patio and deck for you to, vacation 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, Kid friendly
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Inviting apartment with patio, full kitchen, & golf nearby, vacation rental in Chatham
Inviting apartment with patio, full kitchen, & golf nearby, vacation rental in Chatham
Inviting apartment with patio, full kitchen, & golf nearby, vacation rental in Chatham

Inviting apartment with patio, full kitchen, & golf nearby

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Perfect couples escape. Close to beaches, great biking & walking & pet friendly., vacation rental in Chatham
Perfect couples escape. Close to beaches, great biking & walking & pet friendly., vacation rental in Chatham
Perfect couples escape. Close to beaches, great biking & walking & pet friendly., vacation rental in Chatham

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

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, vacation rental in Chatham
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, vacation rental in Chatham
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach, vacation rental in Chatham

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, vacation rental in Chatham
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, vacation rental in Chatham
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham, vacation rental in Chatham

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, vacation rental in Chatham
Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, vacation rental in Chatham
Misty Meadow - Renovated condo-Central AC 109 Misty Meadow Lane #1 N.Chatham, vacation rental in Chatham

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Cute Cottage - Half Mile to Nantucket Sound! (1976), vacation rental in Chatham
Cute Cottage - Half Mile to Nantucket Sound! (1976), vacation rental in Chatham
Cute Cottage - Half Mile to Nantucket Sound! (1976), vacation rental in Chatham

Cute Cottage - Half Mile to Nantucket Sound! (1976)

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Charming Chatham Cottage, vacation rental in Chatham
Charming Chatham Cottage, vacation rental in Chatham
Charming Chatham Cottage, vacation rental in Chatham

Charming Chatham Cottage

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Wonderful cottage located in the heart of downtown Chatham......steps to, vacation rental in Chatham
Wonderful cottage located in the heart of downtown Chatham......steps to, vacation rental in Chatham
Wonderful cottage located in the heart of downtown Chatham......steps to, vacation rental in Chatham

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Stunning Home with Water Views!, vacation rental in Chatham
Stunning Home with Water Views!, vacation rental in Chatham
Stunning Home with Water Views!, vacation rental in Chatham

Stunning Home with Water Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Charming/Great Location/Walk to town/baseball field, vacation rental in Chatham
Charming/Great Location/Walk to town/baseball field, vacation rental in Chatham
Charming/Great Location/Walk to town/baseball field, vacation rental in Chatham

Charming/Great Location/Walk to town/baseball field

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, vacation rental in Chatham
Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, vacation rental in Chatham
Beautiful 2-bed Condo on Serene Frost Fish Creek; Convenient N Chatham location, vacation 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, Kid friendly
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Quaint 2 bedroom home on quiet street., vacation rental in Chatham
Quaint 2 bedroom home on quiet street., vacation rental in Chatham
Quaint 2 bedroom home on quiet street., vacation rental in Chatham

Quaint 2 bedroom home on quiet street.

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

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Kid friendly
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Wrap-Around Porch Mins. to Beach!, vacation rental in Chatham
Wrap-Around Porch Mins. to Beach!, vacation rental in Chatham
Wrap-Around Porch Mins. to Beach!, vacation rental in Chatham

Wrap-Around Porch Mins. to Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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