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Chatham Vacation Rentals

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638 rentals in Chatham.
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Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach, vacation rental in Chatham
Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach, vacation rental in Chatham
Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach, vacation rental in Chatham

Beach Chic Chatham 5⭐ Private-Newly Renov'd-Hear Waves at Night-5m Walk to Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Water View-Walk town/beach, pets considered, Linen Option, vacation rental in Chatham
Water View-Walk town/beach, pets considered, Linen Option, vacation rental in Chatham
Water View-Walk town/beach, pets considered, Linen Option, vacation rental in Chatham

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

Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
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

Rental Home
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated- Large Deck, Fire Pit, Game Room & Many Amenities, vacation rental in Chatham
Newly Renovated- Large Deck, Fire Pit, Game Room & Many Amenities, vacation rental in Chatham
Newly Renovated- Large Deck, Fire Pit, Game Room & Many Amenities, vacation rental in Chatham

Newly Renovated- Large Deck, Fire Pit, Game Room & Many Amenities

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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LOCATION! LOCATION! LOCATION! Water Views!  Walk to beach and walk to town!, vacation rental in Chatham
LOCATION! LOCATION! LOCATION! Water Views!  Walk to beach and walk to town!, vacation rental in Chatham
LOCATION! LOCATION! LOCATION! Water Views!  Walk to beach and walk to town!, vacation rental in Chatham

LOCATION! LOCATION! LOCATION! Water Views! Walk to beach and walk to town!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd, vacation rental in Chatham
Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd, vacation rental in Chatham
Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd, vacation rental in Chatham

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home, vacation rental in Chatham
5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home, vacation rental in Chatham
5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home, vacation rental in Chatham

5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Sanitized! Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, vacation rental in Chatham
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, vacation rental in Chatham
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, vacation rental in Chatham

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Near Harding's Beach, 4 min walk to Oyster River...AC added 2021, vacation rental in Chatham
Near Harding's Beach, 4 min walk to Oyster River...AC added 2021, vacation rental in Chatham
Near Harding's Beach, 4 min walk to Oyster River...AC added 2021, vacation rental in Chatham

Near Harding's Beach, 4 min walk to Oyster River...AC added 2021

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
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5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, vacation rental in Chatham
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, vacation rental in Chatham
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, vacation rental in Chatham

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, vacation rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, vacation rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, vacation rental in Chatham

OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN - Close to Beaches, and Downtown

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, vacation rental in Chatham
Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, vacation rental in Chatham
Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, vacation rental in Chatham

Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Exceptional Chatham Cottage, vacation rental in Chatham
Exceptional Chatham Cottage, vacation rental in Chatham
Exceptional Chatham Cottage, vacation rental in Chatham

Exceptional Chatham Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, vacation rental in Chatham
Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, vacation rental in Chatham
Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, vacation rental in Chatham

Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful home with ocean views! Short walk to the beach!, vacation rental in Chatham
Beautiful home with ocean views! Short walk to the beach!, vacation rental in Chatham
Beautiful home with ocean views! Short walk to the beach!, vacation rental in Chatham

Beautiful home with ocean views! Short walk to the beach!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham
WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham
WATERVIEWS! 4min drive to Hardings Beach!, vacation rental in Chatham

WATERVIEWS! 4min drive to Hardings Beach!

Rental Home
6 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
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Charming Chatham House Walk to Downtown, vacation rental in Chatham
Charming Chatham House Walk to Downtown, vacation rental in Chatham
Charming Chatham House Walk to Downtown, vacation rental in Chatham

Charming Chatham House Walk to Downtown

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, vacation rental in Chatham
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, vacation rental in Chatham
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, vacation rental in Chatham

5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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3 bed 3 bath. Premium linens provided. Pet friendly, vacation rental in Chatham
3 bed 3 bath. Premium linens provided. Pet friendly, vacation rental in Chatham
3 bed 3 bath. Premium linens provided. Pet friendly, vacation rental in Chatham

3 bed 3 bath. Premium linens provided. Pet friendly

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, vacation rental in Chatham
Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, vacation rental in Chatham
Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, vacation rental in Chatham

Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated! Walk to Town and Beach!, vacation rental in Chatham
Newly Renovated! Walk to Town and Beach!, vacation rental in Chatham
Newly Renovated! Walk to Town and Beach!, vacation rental in Chatham

Newly Renovated! Walk to Town and Beach!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, vacation rental in Chatham
5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, vacation rental in Chatham
5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, vacation rental in Chatham

5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, vacation rental in Chatham
Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, vacation rental in Chatham
Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, vacation rental in Chatham

Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., vacation rental in Chatham
Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., vacation rental in Chatham
Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., vacation rental in Chatham

Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach.

Rental Home
8 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Think Sun, Sand, and Surf - New Central Air,  8/10 mi to Beach - $2300/wk 9/3-10, vacation rental in Chatham
Think Sun, Sand, and Surf - New Central Air,  8/10 mi to Beach - $2300/wk 9/3-10, vacation rental in Chatham
Think Sun, Sand, and Surf - New Central Air,  8/10 mi to Beach - $2300/wk 9/3-10, vacation rental in Chatham

Think Sun, Sand, and Surf - New Central Air, 8/10 mi to Beach - $2300/wk 9/3-10

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Views of  Nantucket  Sound and Walk to 2 Beaches from Charming Cape Cod Cottage., vacation rental in Chatham
Views of  Nantucket  Sound and Walk to 2 Beaches from Charming Cape Cod Cottage., vacation rental in Chatham
Views of  Nantucket  Sound and Walk to 2 Beaches from Charming Cape Cod Cottage., vacation rental in Chatham

Views of Nantucket Sound and Walk to 2 Beaches from Charming Cape Cod Cottage.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chatham-Walk to Town/Beach-Multi Family Friendly, vacation rental in Chatham
Chatham-Walk to Town/Beach-Multi Family Friendly, vacation rental in Chatham
Chatham-Walk to Town/Beach-Multi Family Friendly, vacation rental in Chatham

Chatham-Walk to Town/Beach-Multi Family Friendly

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, vacation rental in Chatham
#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, vacation rental in Chatham
#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, vacation rental in Chatham

#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, vacation rental in Chatham
Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, vacation rental in Chatham
Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, vacation rental in Chatham

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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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
3 bathrooms
Sleeps 8
Match: Sleeps
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Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families, vacation rental in Chatham
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families, vacation rental in Chatham
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families, vacation rental in Chatham

Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, vacation rental in Chatham
16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, vacation rental in Chatham
16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, vacation rental in Chatham

16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot

Rental Home
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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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
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Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, vacation rental in Chatham
Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, vacation rental in Chatham
Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, vacation rental in Chatham

Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly

Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**, vacation rental in Chatham
4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**, vacation rental in Chatham
4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**, vacation rental in Chatham

4BR+Loft Beautiful Chatham-Year Round-Sleeps up to 8 & 1 Mile to Town **Video**

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming  Waterfront House  in Chatham, vacation rental in Chatham
Charming  Waterfront House  in Chatham, vacation rental in Chatham
Charming  Waterfront House  in Chatham, vacation rental in Chatham

Charming Waterfront House in Chatham

Rental Home
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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ELBOW INN ,Private Retreat with Two Master Suites, vacation rental in Chatham
ELBOW INN ,Private Retreat with Two Master Suites, vacation rental in Chatham
ELBOW INN ,Private Retreat with Two Master Suites, vacation rental in Chatham

ELBOW INN ,Private Retreat with Two Master Suites

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, vacation rental in Chatham
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, vacation rental in Chatham
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, vacation rental in Chatham

Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, vacation rental in Chatham
Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, vacation rental in Chatham
Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, vacation rental in Chatham

Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, vacation rental in Chatham
"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, vacation rental in Chatham
"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, vacation rental in Chatham

"Cape Escape" Sunny Renovated House - Walk To Beach & Tennis, Central AC/WiFi

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, vacation rental in Chatham
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, vacation rental in Chatham
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, vacation rental in Chatham

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic Cape house within walking distance of beach, bike trail, and restaurants, vacation rental in Chatham
Classic Cape house within walking distance of beach, bike trail, and restaurants, vacation rental in Chatham
Classic Cape house within walking distance of beach, bike trail, and restaurants, vacation rental in Chatham

Classic Cape house within walking distance of beach, bike trail, and restaurants

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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