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Holiday Rentals in Chatham

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

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

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

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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Convenient to all amenities and beaches in Chatham, holiday rental in Chatham
Convenient to all amenities and beaches in Chatham, holiday rental in Chatham
Convenient to all amenities and beaches in Chatham, holiday rental in Chatham

Convenient to all amenities and beaches in Chatham

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

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

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

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

Holiday Rental House
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, holiday rental in Chatham
Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd, holiday rental in Chatham
Beach Chic Chatham 5 ⭐ Family Retreat-5 min walk to Private Beach-Newly Renov'd, holiday rental in Chatham

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

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

5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach, holiday rental in Chatham

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday rental in Chatham
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, holiday 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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Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, holiday rental in Chatham
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, holiday rental in Chatham
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!, holiday 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, holiday rental in Chatham
Near Harding's Beach, 4 min walk to Oyster River...AC added 2021, holiday rental in Chatham
Near Harding's Beach, 4 min walk to Oyster River...AC added 2021, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
3 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
More info
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5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, holiday rental in Chatham
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, holiday rental in Chatham
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!, holiday rental in Chatham

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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, holiday rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, holiday rental in Chatham
OYSTER POND NEWLY RENOVATED OPEN FLOOR PLAN  - Close to Beaches, and Downtown, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, holiday rental in Chatham
Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, holiday rental in Chatham
Chatham Village Center 3br - In Town & Near Beach/Chatham Bars Inn, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Exceptional Chatham Cottage, holiday rental in Chatham
Exceptional Chatham Cottage, holiday rental in Chatham
Exceptional Chatham Cottage, holiday rental in Chatham

Exceptional Chatham Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, holiday rental in Chatham
Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, holiday rental in Chatham
Heart Of Chatham Village - Beach/Chatham Bars Inn/Main Street, holiday rental in Chatham

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

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

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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
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WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham
WATERVIEWS! 4min drive to Hardings Beach!, holiday rental in Chatham

WATERVIEWS! 4min drive to Hardings Beach!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
More info
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Charming Chatham House Walk to Downtown, holiday rental in Chatham
Charming Chatham House Walk to Downtown, holiday rental in Chatham
Charming Chatham House Walk to Downtown, holiday rental in Chatham

Charming Chatham House Walk to Downtown

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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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
More info
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5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, holiday rental in Chatham
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, holiday rental in Chatham
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet, holiday rental in Chatham

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Newly Renovated! Walk to Town and Beach!, holiday rental in Chatham
Newly Renovated! Walk to Town and Beach!, holiday rental in Chatham
Newly Renovated! Walk to Town and Beach!, holiday rental in Chatham

Newly Renovated! Walk to Town and Beach!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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3 bed 3 bath. Premium linens provided. Pet friendly, holiday rental in Chatham
3 bed 3 bath. Premium linens provided. Pet friendly, holiday rental in Chatham
3 bed 3 bath. Premium linens provided. Pet friendly, holiday rental in Chatham

3 bed 3 bath. Premium linens provided. Pet friendly

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, holiday rental in Chatham
Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, holiday rental in Chatham
Beautiful 2-Bed Condo on Frost Fish Creek; Convenient Location; Serene Setting, holiday 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
More info
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5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, holiday rental in Chatham
5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, holiday rental in Chatham
5 Bed/2 Bath Cottage Sleeps 11. Walk to Restaurants & More, holiday rental in Chatham

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, holiday rental in Chatham
Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, holiday rental in Chatham
Location! Pool and Spa! 2 Primary Suites, Walk to Town, CBI, Beach, holiday rental in Chatham

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., holiday rental in Chatham
Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., holiday rental in Chatham
Chatham Family Estate. Heated Pool. Sleeps 16+, AC, walk to town and beach., holiday rental in Chatham

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

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

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

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Chatham-Walk to Town/Beach-Multi Family Friendly, holiday rental in Chatham
Chatham-Walk to Town/Beach-Multi Family Friendly, holiday rental in Chatham
Chatham-Walk to Town/Beach-Multi Family Friendly, holiday rental in Chatham

Chatham-Walk to Town/Beach-Multi Family Friendly

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, holiday rental in Chatham
#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, holiday rental in Chatham
#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, holiday rental in Chatham
Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, holiday rental in Chatham
Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home, holiday rental in Chatham

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

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

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, holiday rental in Chatham
16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, holiday rental in Chatham
16638: Perfect for a Group w/ Kids & Dogs! Close to the Beach & Town, w/ Hot, holiday rental in Chatham

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday rental in Chatham
Lovely Stage Harbor Estate Guest House W/Private Beach to Use, holiday 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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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
More info
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Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, holiday rental in Chatham
Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, holiday rental in Chatham
Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly, holiday rental in Chatham

Private Beach, Gorgeous Neighborhood, Lovely Home, Pet Friendly

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

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming  Waterfront House  in Chatham, holiday rental in Chatham
Charming  Waterfront House  in Chatham, holiday rental in Chatham
Charming  Waterfront House  in Chatham, holiday rental in Chatham

Charming Waterfront House in Chatham

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
More info
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ELBOW INN ,Private Retreat with Two Master Suites, holiday rental in Chatham
ELBOW INN ,Private Retreat with Two Master Suites, holiday rental in Chatham
ELBOW INN ,Private Retreat with Two Master Suites, holiday rental in Chatham

ELBOW INN ,Private Retreat with Two Master Suites

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, holiday rental in Chatham
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, holiday rental in Chatham
Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis, holiday rental in Chatham

Charming Air Conditioned Chatham Vacation Home Walk to Beach & Tennis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, holiday rental in Chatham
Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, holiday rental in Chatham
Sunny, Clean & Spacious on Quiet Cul-de-Sac; Walk to Ridgevale Beach, holiday 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
More info
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"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, holiday rental in Chatham
"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, holiday rental in Chatham
"Cape Escape" Sunny Renovated House -  Walk To Beach & Tennis, Central AC/WiFi, holiday rental in Chatham

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, holiday rental in Chatham
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, holiday rental in Chatham
Historic Waterfront Home with Sweeping Chatham Water Views! Pet Friendly!, holiday rental in Chatham

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham
Renovated cottage 1 mile to beach in Chatham!, holiday rental in Chatham

Renovated cottage 1 mile to beach in Chatham!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Classic Cape house within walking distance of beach, bike trail, and restaurants, holiday rental in Chatham
Classic Cape house within walking distance of beach, bike trail, and restaurants, holiday rental in Chatham
Classic Cape house within walking distance of beach, bike trail, and restaurants, holiday rental in Chatham

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

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