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Chatham Vacation Rentals

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Bedrooms

Bathrooms

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5 km
638 rentals in Chatham.
Pleasant Forest Shores cottages #4 : So. Chatham, vacation rental in Chatham
Pleasant Forest Shores cottages #4 : So. Chatham, vacation rental in Chatham
Pleasant Forest Shores cottages #4 : So. Chatham, vacation rental in Chatham

Pleasant Forest Shores cottages #4 : So. Chatham

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful home near Jacknife Beach and bike trail, vacation rental in Chatham
Beautiful home near Jacknife Beach and bike trail, vacation rental in Chatham
Beautiful home near Jacknife Beach and bike trail, vacation rental in Chatham

Beautiful home near Jacknife Beach and bike trail

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Convenient to all amenities and beaches in Chatham, vacation rental in Chatham
Convenient to all amenities and beaches in Chatham, vacation rental in Chatham
Convenient to all amenities and beaches in Chatham, vacation rental in Chatham

Convenient to all amenities and beaches in Chatham

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, vacation rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, vacation rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, vacation rental in Chatham

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 3b/2ba House Close to Downtown/Pier/Beach, vacation rental in Chatham
Charming 3b/2ba House Close to Downtown/Pier/Beach, vacation rental in Chatham
Charming 3b/2ba House Close to Downtown/Pier/Beach, vacation rental in Chatham

Charming 3b/2ba House Close to Downtown/Pier/Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated cottage 1 mile to beach in Chatham!, vacation rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, vacation rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, vacation rental in Chatham

Renovated cottage 1 mile to beach in Chatham!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Outermost Waterfront Chatham Home w/ Wraparound Views, vacation rental in Chatham
Outermost Waterfront Chatham Home w/ Wraparound Views, vacation rental in Chatham
Outermost Waterfront Chatham Home w/ Wraparound Views, vacation rental in Chatham

Outermost Waterfront Chatham Home w/ Wraparound Views

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, vacation rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, vacation rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, vacation rental in Chatham

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chatham Walk to Beach Cape Cod, vacation rental in Chatham
Chatham Walk to Beach Cape Cod, vacation rental in Chatham
Chatham Walk to Beach Cape Cod, vacation rental in Chatham

Chatham Walk to Beach Cape Cod

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 Bedrooms, 2 Baths, Sleeps 8, vacation rental in Chatham
4 Bedrooms, 2 Baths, Sleeps 8, vacation rental in Chatham
4 Bedrooms, 2 Baths, Sleeps 8, vacation rental in Chatham

4 Bedrooms, 2 Baths, Sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Chatham Cape Cod Vacation Rental (15578), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (15578), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (15578), vacation rental in Chatham

Chatham Cape Cod Vacation Rental (15578)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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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!

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, 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
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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
More info
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Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, vacation rental in Chatham
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, vacation rental in Chatham
Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!, vacation rental in Chatham

Ocean-Front Condo Sleeps 6 (Light-filled end unit facing Ocean on Starfish Ln)!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxurious Home with Pool & Game Room in Cape Cod, vacation rental in Chatham
Luxurious Home with Pool & Game Room in Cape Cod, vacation rental in Chatham
Luxurious Home with Pool & Game Room in Cape Cod, vacation rental in Chatham

Luxurious Home with Pool & Game Room in Cape Cod

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, vacation rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, vacation rental in Chatham
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C, vacation rental in Chatham

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Renovated, modern Chatham beach house with lots of cozy charm, vacation rental in Chatham
Renovated, modern Chatham beach house with lots of cozy charm, vacation rental in Chatham
Renovated, modern Chatham beach house with lots of cozy charm, vacation rental in Chatham

Renovated, modern Chatham beach house with lots of cozy charm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Harwich home with private pool in great location!, vacation rental in Chatham
Beautiful Harwich home with private pool in great location!, vacation rental in Chatham
Beautiful Harwich home with private pool in great location!, vacation rental in Chatham

Beautiful Harwich home with private pool in great location!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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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...

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, vacation rental in Chatham
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, vacation rental in Chatham
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views, vacation rental in Chatham

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Chatham Cape Cod Vacation Rental (16729), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (16729), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (16729), vacation rental in Chatham

Chatham Cape Cod Vacation Rental (16729)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chatham Cape Cod Vacation Rental (15639), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (15639), vacation rental in Chatham
Chatham Cape Cod Vacation Rental (15639), vacation rental in Chatham

Chatham Cape Cod Vacation Rental (15639)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Chatham Cape Cod Waterfront Vacation Rental (12273), vacation rental in Chatham
Chatham Cape Cod Waterfront Vacation Rental (12273), vacation rental in Chatham
Chatham Cape Cod Waterfront Vacation Rental (12273), vacation rental in Chatham

Chatham Cape Cod Waterfront Vacation Rental (12273)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Walk to Ridgevale Beach From Family Friendly Home, vacation rental in Chatham
Walk to Ridgevale Beach From Family Friendly Home, vacation rental in Chatham
Walk to Ridgevale Beach From Family Friendly Home, vacation rental in Chatham

Walk to Ridgevale Beach From Family Friendly Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Carriage House with Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham
Carriage House with Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham
Carriage House with Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham

Carriage House with Beautiful Water View, Steps to Beach & Main Street

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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5 Star Waterfront in North Chatham with dock, fire pit, and beach, vacation rental in Chatham
5 Star Waterfront in North Chatham with dock, fire pit, and beach, vacation rental in Chatham
5 Star Waterfront in North Chatham with dock, fire pit, and beach, vacation rental in Chatham

5 Star Waterfront in North Chatham with dock, fire pit, and beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use, vacation rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, vacation rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, vacation rental in Chatham

Lovely Stage Harbor Estate Guest House W/Private Beach to Use

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, vacation rental in Chatham
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, vacation rental in Chatham
Lovely cottage near beach and town - screened porch, outdoor shower, picnic area, vacation rental in Chatham

Lovely cottage near beach and town - screened porch, outdoor shower, picnic area

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Cozy Cape near Chatham Center, vacation rental in Chatham
Cozy Cape near Chatham Center, vacation rental in Chatham
Cozy Cape near Chatham Center, vacation rental in Chatham

Cozy Cape near Chatham Center

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, vacation rental in Chatham
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, vacation rental in Chatham
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!, vacation rental in Chatham

PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Chatham Cape Cod Vacation Rental (50), vacation rental in Chatham
South Chatham Cape Cod Vacation Rental (50), vacation rental in Chatham
South Chatham Cape Cod Vacation Rental (50), vacation rental in Chatham

South Chatham Cape Cod Vacation Rental (50)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham
Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street, vacation rental in Chatham

Sea Captain's House - Beautiful Water View, Steps to Beach & Main Street

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
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Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, vacation rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, vacation rental in Chatham
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, vacation 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
More info
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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
More info
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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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, vacation rental in Chatham
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, vacation rental in Chatham
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches, vacation rental in Chatham

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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South Chatham Cape Cod Vacation Rental (14295), vacation rental in Chatham
South Chatham Cape Cod Vacation Rental (14295), vacation rental in Chatham
South Chatham Cape Cod Vacation Rental (14295), vacation rental in Chatham

South Chatham Cape Cod Vacation Rental (14295)

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, vacation rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, vacation rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN, vacation rental in Chatham

OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., vacation rental in Chatham
Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., vacation rental in Chatham
Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails., vacation rental in Chatham

Relaxing, peaceful area close to beaches, downtown Chatham, and walking trails.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Newly Renovated Cape House .9Miles from the Beach, vacation rental in Chatham
Newly Renovated Cape House .9Miles from the Beach, vacation rental in Chatham
Newly Renovated Cape House .9Miles from the Beach, vacation rental in Chatham

Newly Renovated Cape House .9Miles from the Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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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!!!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., vacation rental in Chatham
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., vacation rental in Chatham
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants., vacation rental in Chatham

Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 638
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