Vacation rentals in Wingaersheek Beach, MA

123 available vacation rental offers

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Best vacation rentals and Airbnb offers in Wingaersheek Beach, MA

Harborside Oasis ★ Harbor View ★ Heart of Downtown - Wingaersheek Beach, MA

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Apartment, Wingaersheek Beach

Harborside Oasis ★ Harbor View ★ Heart of Downtown is a apartment in Wingaersheek Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown is a apartment in Wingaersheek Beach, 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 wifi, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,645.

From$235/night
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Good Harbor Beach Apt.- 6/10 mile - Wingaersheek Beach, MA

Good Harbor Beach Apt.- 6/10 mile

Apartment, Wingaersheek Beach

Good Harbor Beach Apt.- 6/10 mile is a apartment in Wingaersheek Beach, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Good Harbor Beach Apt.- 6/10 mile

Good Harbor Beach Apt.- 6/10 mile is a apartment in Wingaersheek Beach, 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 $1,743.

From$249/night
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Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass - Wingaersheek Beach, MA

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass

Holiday Home, Wingaersheek Beach

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass is a holiday home in Wingaersheek Beach, with easy beach access and room for a group. This stay gives…

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About Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass is a holiday home in Wingaersheek Beach, with easy beach 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$255/night
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Large 2 room studio with full kitchen and deck - Wingaersheek Beach, MA

Large 2 room studio with full kitchen and deck

Apartment, Wingaersheek Beach

Large 2 room studio with full kitchen and deck is a apartment in Wingaersheek Beach, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Large 2 room studio with full kitchen and deck

Large 2 room studio with full kitchen and deck is a apartment in Wingaersheek Beach, with pet-friendly space, outdoor space, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,194.

From$313/night
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Waterfront vacation rentals in Wingaersheek Beach, MA

Discover vacation rentals close to the coast, water, and beach areas around Wingaersheek Beach, MA.

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. - Wingaersheek Beach, MA

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking.

Cottage, Wingaersheek Beach

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. is a cottage in Wingaersheek Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking.

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. is a cottage in Wingaersheek Beach, 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 $2,785.

From$398/night
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach - Wingaersheek Beach, MA

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

Holiday Home, Wingaersheek Beach

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach is a holiday home in Wingaersheek Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About 3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach is a holiday home in Wingaersheek Beach, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,958.

From$423/night
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Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! - Wingaersheek Beach, MA

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants!

Apartment, Wingaersheek Beach

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! is a apartment in Wingaersheek Beach, with easy beach access, parking, and kitchen access. This stay gives…

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About Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants!

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! is a apartment in Wingaersheek Beach, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,006.

From$429/night
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Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor - Wingaersheek Beach, MA

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor

Condo, Wingaersheek Beach

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor is a condo in Wingaersheek Beach, with easy beach access and kitchen access. This stay gives travelers a comfortable…

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About Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor is a condo in Wingaersheek Beach, 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 beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,200.

From$457/night
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Vacation rentals with a pool in Wingaersheek Beach, MA

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

Whole House Steps from Pleasant Pond - Wingaersheek Beach, MA

Whole House Steps from Pleasant Pond

Holiday Home, Wingaersheek Beach

Whole House Steps from Pleasant Pond is a holiday home in Wingaersheek Beach, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring…

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About Whole House Steps from Pleasant Pond

Whole House Steps from Pleasant Pond is a holiday home in Wingaersheek Beach, with pet-friendly space, pool 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: pool, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,799.

From$257/night
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Charming 1-bedroom Guest suite in amazing Manchester-by-the-Sea with WiFi, AC - Wingaersheek Beach, MA

Charming 1-bedroom Guest suite in amazing Manchester-by-the-Sea with WiFi, AC

Apartment, Wingaersheek Beach

Charming 1-bedroom Guest suite in amazing Manchester-by-the-Sea with WiFi, AC is a apartment in Wingaersheek Beach, with pet-friendly space, pool access, and room for a group. This stay…

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About Charming 1-bedroom Guest suite in amazing Manchester-by-the-Sea with WiFi, AC

Charming 1-bedroom Guest suite in amazing Manchester-by-the-Sea with WiFi, AC is a apartment in Wingaersheek Beach, with pet-friendly space, pool 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,499.

From$357/night
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Spacious 1790 Captain's estate, large pool, near beautiful beach - Wingaersheek Beach, MA

Spacious 1790 Captain's estate, large pool, near beautiful beach

Holiday Home, Wingaersheek Beach

Spacious 1790 Captain's estate, large pool, near beautiful beach is a holiday home in Wingaersheek Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About Spacious 1790 Captain's estate, large pool, near beautiful beach

Spacious 1790 Captain's estate, large pool, near beautiful beach is a holiday home in Wingaersheek Beach, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,469.

From$1,496/night
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Vacation rentals with parking in Wingaersheek Beach, MA

Find vacation rentals that make arriving by car easier.

The Orca – Modern Coastal Comfort Awaits - Wingaersheek Beach, MA

The Orca – Modern Coastal Comfort Awaits

Apartment, Wingaersheek Beach

The Orca – Modern Coastal Comfort Awaits is a apartment in Wingaersheek Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Orca – Modern Coastal Comfort Awaits

The Orca – Modern Coastal Comfort Awaits is a apartment in Wingaersheek Beach, 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,605.

From$372/night
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Sea Glass House - Tranquil Retreat or Base for Adventure - Wingaersheek Beach, MA

Sea Glass House - Tranquil Retreat or Base for Adventure

Apartment, Wingaersheek Beach

Sea Glass House - Tranquil Retreat or Base for Adventure is a apartment in Wingaersheek Beach, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Sea Glass House - Tranquil Retreat or Base for Adventure

Sea Glass House - Tranquil Retreat or Base for Adventure is a apartment in Wingaersheek Beach, with parking, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,484.

From$498/night
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Cape Ann Reset - Wingaersheek Beach, MA

Cape Ann Reset

Holiday Home, Wingaersheek Beach

Cape Ann Reset is a holiday home in Wingaersheek Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cape Ann Reset

Cape Ann Reset is a holiday home in Wingaersheek Beach, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,569.

From$510/night
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Delightful 3-bedroom house with AC in charming Gloucester. - Wingaersheek Beach, MA

Delightful 3-bedroom house with AC in charming Gloucester.

Holiday Home, Wingaersheek Beach

Delightful 3-bedroom house with AC in charming Gloucester. is a holiday home in Wingaersheek Beach, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Delightful 3-bedroom house with AC in charming Gloucester.

Delightful 3-bedroom house with AC in charming Gloucester. is a holiday home in Wingaersheek Beach, 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 $4,129.

From$590/night
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Pet-friendly vacation rentals in Wingaersheek Beach, MA

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

Mill Lane: Enjoy all of Rockport's charms, right outside your door. - Wingaersheek Beach, MA

Mill Lane: Enjoy all of Rockport's charms, right outside your door.

Holiday Home, Wingaersheek Beach

Mill Lane: Enjoy all of Rockport's charms, right outside your door. is a holiday home in Wingaersheek Beach, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Mill Lane: Enjoy all of Rockport's charms, right outside your door.

Mill Lane: Enjoy all of Rockport's charms, right outside your door. is a holiday home in Wingaersheek Beach, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,708.

From$387/night
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Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly - Wingaersheek Beach, MA

Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly

Holiday Home, Wingaersheek Beach

Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly is a holiday home in Wingaersheek Beach, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly

Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly is a holiday home in Wingaersheek Beach, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,923.

From$418/night
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Rockport Getaway Near Shops & Beaches - Wingaersheek Beach, MA

Rockport Getaway Near Shops & Beaches

Holiday Home, Wingaersheek Beach

Rockport Getaway Near Shops & Beaches is a holiday home in Wingaersheek Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Rockport Getaway Near Shops & Beaches

Rockport Getaway Near Shops & Beaches is a holiday home in Wingaersheek Beach, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,110.

From$444/night
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~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun - Wingaersheek Beach, MA

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun

Holiday Home, Wingaersheek Beach

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun is a holiday home in Wingaersheek Beach, with pet-friendly space, easy beach access, and kitchen access.…

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About ~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun is a holiday home in Wingaersheek Beach, 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 $3,429.

From$490/night
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Vacation rentals with a kitchen in Wingaersheek Beach, MA

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

Charming 2-bedroom apartment in serene Rockport neighborhood - Wingaersheek Beach, MA

Charming 2-bedroom apartment in serene Rockport neighborhood

Apartment, Wingaersheek Beach

Charming 2-bedroom apartment in serene Rockport neighborhood is a apartment in Wingaersheek Beach, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom apartment in serene Rockport neighborhood

Charming 2-bedroom apartment in serene Rockport neighborhood is a apartment in Wingaersheek Beach, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,598.

From$514/night
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Twin Lights: Explore the village of Rockport! - Wingaersheek Beach, MA

Twin Lights: Explore the village of Rockport!

Holiday Home, Wingaersheek Beach

Twin Lights: Explore the village of Rockport! is a holiday home in Wingaersheek Beach, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Twin Lights: Explore the village of Rockport!

Twin Lights: Explore the village of Rockport! is a holiday home in Wingaersheek Beach, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,605.

From$515/night
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5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! - Wingaersheek Beach, MA

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!

Holiday Home, Wingaersheek Beach

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! is a holiday home in Wingaersheek Beach, with easy beach access and kitchen access. This stay gives travelers a…

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About 5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! is a holiday home in Wingaersheek Beach, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,647.

From$521/night
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Helena House: Close to Plum Cove Beach - Wingaersheek Beach, MA

Helena House: Close to Plum Cove Beach

Holiday Home, Wingaersheek Beach

Helena House: Close to Plum Cove Beach is a holiday home in Wingaersheek Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Helena House: Close to Plum Cove Beach

Helena House: Close to Plum Cove Beach is a holiday home in Wingaersheek Beach, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,524.

From$646/night
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