Vacation rentals in South Chatham, MA

Best vacation rentals and Airbnb offers in South Chatham, MA

Riviera Sunset

Holiday Home, South Chatham

Riviera Sunset is a holiday home in South Chatham, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Riviera Sunset

Riviera Sunset is a holiday home in South Chatham, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: beachfront, beach front, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,230.

From$273/night

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Sea House

Holiday Home, South Chatham

Sea House is a holiday home in South Chatham. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Sea House

Sea House is a holiday home in South Chatham. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and fishing.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,545.

From$410/night

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South Chatham Sunshine

Holiday Home, South Chatham

South Chatham Sunshine is a holiday home in South Chatham, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About South Chatham Sunshine

South Chatham Sunshine is a holiday home in South Chatham, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, family friendly, and game room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,045.

From$443/night

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TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH

Holiday Home, South Chatham

TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

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About TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH

TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,058.

From$294/night

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Vacation rentals with a pool in South Chatham, MA

Add a pool to the search when you want an easy place to cool off between outings.

PANORAMIC OCEAN VIEWS!

Condo, South Chatham

PANORAMIC OCEAN VIEWS! is a condo in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About PANORAMIC OCEAN VIEWS!

PANORAMIC OCEAN VIEWS! is a condo in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,261.

From$752/night

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Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Holiday Home, South Chatham

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks is a holiday home in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks is a holiday home in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,482.

From$1,212/night

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

Holiday Home, South Chatham

Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C is a holiday home in South Chatham, with pet-friendly space, pool access, and easy beach access. This stay…

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

Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C is a holiday home in South Chatham, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,006.

From$1,287/night

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Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Holiday Home, South Chatham

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks is a holiday home in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks is a holiday home in South Chatham, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,451.

From$1,636/night

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Vacation rentals with parking in South Chatham, MA

Find vacation rentals that make arriving by car easier.

Cozy 1 bedroom with fenced in yard, porch, close to the bay beach & bike trail.

Apartment, South Chatham

Cozy 1 bedroom with fenced in yard, porch, close to the bay beach & bike trail. is a apartment in South Chatham, with easy beach access, parking, and kitchen access. This stay gives…

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About Cozy 1 bedroom with fenced in yard, porch, close to the bay beach & bike trail.

Cozy 1 bedroom with fenced in yard, porch, close to the bay beach & bike trail. is a apartment in South Chatham, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,617.

From$231/night

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Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Apartment, South Chatham

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home is a apartment in South Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home is a apartment in South Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,255.

From$322/night

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Harwich Hideaway, Close to Beach, Bike Path & 10 minutes away from Chatham!

Holiday Home, South Chatham

Harwich Hideaway, Close to Beach, Bike Path & 10 minutes away from Chatham! is a holiday home in South Chatham, with easy beach access, parking, and kitchen access. This stay gives…

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About Harwich Hideaway, Close to Beach, Bike Path & 10 minutes away from Chatham!

Harwich Hideaway, Close to Beach, Bike Path & 10 minutes away from Chatham! is a holiday home in South Chatham, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,393.

From$485/night

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Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!

Holiday Home, South Chatham

Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views! is a holiday home in South Chatham, with easy beach access, parking, and kitchen access. This stay gives…

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About Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!

Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views! is a holiday home in South Chatham, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,511.

From$502/night

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Pet-friendly vacation rentals in South Chatham, MA

Bring your pet along with stays that welcome four-legged travelers.

Chatham Tails & Trails!

Holiday Home, South Chatham

Chatham Tails & Trails! is a holiday home in South Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Chatham Tails & Trails!

Chatham Tails & Trails! is a holiday home in South Chatham, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,394.

From$485/night

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Relaxing 3br, private yard, walk to beach, close to bike trail and shopping!

Holiday Home, South Chatham

Relaxing 3br, private yard, walk to beach, close to bike trail and shopping! is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Relaxing 3br, private yard, walk to beach, close to bike trail and shopping!

Relaxing 3br, private yard, walk to beach, close to bike trail and shopping! is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,817.

From$545/night

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Star of the Sea - Newly Renovated Cape House .9Miles from the Beach

Holiday Home, South Chatham

Star of the Sea - Newly Renovated Cape House .9Miles from the Beach is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Star of the Sea - Newly Renovated Cape House .9Miles from the Beach

Star of the Sea - Newly Renovated Cape House .9Miles from the Beach is a holiday home in South Chatham, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,916.

From$559/night

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Beachside Bliss: Dog Friendly Breezy Stay

Holiday Home, South Chatham

Beachside Bliss: Dog Friendly Breezy Stay is a holiday home in South Chatham, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Beachside Bliss: Dog Friendly Breezy Stay

Beachside Bliss: Dog Friendly Breezy Stay is a holiday home in South Chatham, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,303.

From$603/night

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Vacation rentals with a kitchen in South Chatham, MA

Compare stays with kitchen access for longer trips and easier meals.

Charming Chatham Beach House; Walk to Hardings Beach

Holiday Home, South Chatham

Charming Chatham Beach House; Walk to Hardings Beach is a holiday home in South Chatham, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Charming Chatham Beach House; Walk to Hardings Beach

Charming Chatham Beach House; Walk to Hardings Beach is a holiday home in South Chatham, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,288.

From$470/night

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Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach

Holiday Home, South Chatham

Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach is a holiday home in South Chatham, with easy beach access, kitchen access, and room for a group. This stay gives…

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About Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach

Four Bedroom - Just 6/10's of a Mile to Nantucket Sound Forest Beach is a holiday home in South Chatham, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,665.

From$524/night

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Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities

Holiday Home, South Chatham

Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities is a holiday home in South Chatham, with kitchen access. This stay gives travelers a comfortable base for…

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About Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities

Walk to the warm waters of Nantucket sound 3B/2B home CA, W & D, all amenities is a holiday home in South Chatham, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,680.

From$526/night

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Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches

Holiday Home, South Chatham

Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches is a holiday home in South Chatham, with easy beach access and kitchen access. This stay gives travelers a…

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About Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches

Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches is a holiday home in South Chatham, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,954.

From$565/night

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Family-friendly vacation rentals in South Chatham, MA

Plan a trip with stays that give families more room to spread out.

Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away.

Cottage, South Chatham

Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away. is a cottage in South Chatham, with parking, kitchen access, and room for a group. This stay gives travelers…

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About Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away.

Cozy 1 bedroom cottage in beautiful Orleans with AC. A perfect spot to get away. is a cottage in South Chatham, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,056.

From$294/night

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Colorful clapboard cottage perfect for 2!

Cottage, South Chatham

Colorful clapboard cottage perfect for 2! is a cottage in South Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Colorful clapboard cottage perfect for 2!

Colorful clapboard cottage perfect for 2! is a cottage in South Chatham, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, onsite parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,144.

From$306/night

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Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!

Holiday Home, South Chatham

Peaceful, Charming, Quiet, Airy, Cozy - Take A Look! is a holiday home in South Chatham, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for…

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About Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!

Peaceful, Charming, Quiet, Airy, Cozy - Take A Look! is a holiday home in South Chatham, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,917.

From$417/night

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

Holiday Home, South Chatham

Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house! is a holiday home in South Chatham, with pet-friendly space, easy beach access, and parking. This stay gives…

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

Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house! is a holiday home in South Chatham, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,479.

From$497/night

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