Vacation rentals in Surfside Beach, MA

88 available vacation rental offers

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Best vacation rentals and Airbnb offers in Surfside Beach, MA

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport - Surfside Beach, MA

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport

Apartment, Surfside Beach

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport is a apartment in Surfside Beach, with room for a group and a quieter setting. This stay gives travelers a comfortable base for…

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About Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport is a apartment in Surfside Beach, with room for a group 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,553.

From$650/night
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One Prime week left in August, 8/22 - 8/29 and All of Sept! - Surfside Beach, MA

One Prime week left in August, 8/22 - 8/29 and All of Sept!

Holiday Home, Surfside Beach

One Prime week left in August, 8/22 - 8/29 and All of Sept! is a holiday home in Surfside Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About One Prime week left in August, 8/22 - 8/29 and All of Sept!

One Prime week left in August, 8/22 - 8/29 and All of Sept! is a holiday home in Surfside 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,800.

From$686/night
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Beautiful 1- private bedroom in soothing Nantucket near the airport - Surfside Beach, MA

Beautiful 1- private bedroom in soothing Nantucket near the airport

Apartment, Surfside Beach

Beautiful 1- private bedroom in soothing Nantucket near the airport is a apartment in Surfside Beach, with room for a group. This stay gives travelers a comfortable base for exploring the…

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About Beautiful 1- private bedroom in soothing Nantucket near the airport

Beautiful 1- private bedroom in soothing Nantucket near the airport is a apartment in Surfside Beach, 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: free cancellation, non smoking, hair dryer, and shower.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,458.

From$780/night
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Surfside Beach Cottage----8 Minute Walk To The Beach - Surfside Beach, MA

Surfside Beach Cottage----8 Minute Walk To The Beach

Cottage, Surfside Beach

Surfside Beach Cottage----8 Minute Walk To The Beach is a cottage in Surfside Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Surfside Beach Cottage----8 Minute Walk To The Beach

Surfside Beach Cottage----8 Minute Walk To The Beach is a cottage in Surfside 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 $5,468.

From$781/night
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Waterfront vacation rentals in Surfside Beach, MA

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

Madaket Beach House- Walk to Beach- Private Nantucket Home. - Surfside Beach, MA

Madaket Beach House- Walk to Beach- Private Nantucket Home.

Holiday Home, Surfside Beach

Madaket Beach House- Walk to Beach- Private Nantucket Home. is a holiday home in Surfside Beach, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Madaket Beach House- Walk to Beach- Private Nantucket Home.

Madaket Beach House- Walk to Beach- Private Nantucket Home. is a holiday home in Surfside 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,642.

From$949/night
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Classic Nantucket Home with Ocean Views! - Surfside Beach, MA

Classic Nantucket Home with Ocean Views!

Holiday Home, Surfside Beach

Classic Nantucket Home with Ocean Views! is a holiday home in Surfside Beach, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Classic Nantucket Home with Ocean Views!

Classic Nantucket Home with Ocean Views! is a holiday home in Surfside 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,349.

From$1,050/night
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Nantucket Loft w/ Harbor Views and walk to town - Surfside Beach, MA

Nantucket Loft w/ Harbor Views and walk to town

Apartment, Surfside Beach

Nantucket Loft w/ Harbor Views and walk to town is a apartment in Surfside Beach, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Nantucket Loft w/ Harbor Views and walk to town

Nantucket Loft w/ Harbor Views and walk to town is a apartment in Surfside Beach, with pet-friendly 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,990.

From$1,427/night
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Private Nantucket Cottage Walk to Surfside Beach - Surfside Beach, MA

Private Nantucket Cottage Walk to Surfside Beach

Holiday Home, Surfside Beach

Private Nantucket Cottage Walk to Surfside Beach is a holiday home in Surfside Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private Nantucket Cottage Walk to Surfside Beach

Private Nantucket Cottage Walk to Surfside Beach is a holiday home in Surfside 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,143.

From$1,735/night
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Vacation rentals with a pool in Surfside Beach, MA

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

Large, Renovated Naushop Home, Perfect for 1 or 2 Families! - Surfside Beach, MA

Large, Renovated Naushop Home, Perfect for 1 or 2 Families!

Holiday Home, Surfside Beach

Large, Renovated Naushop Home, Perfect for 1 or 2 Families! is a holiday home in Surfside Beach, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Large, Renovated Naushop Home, Perfect for 1 or 2 Families!

Large, Renovated Naushop Home, Perfect for 1 or 2 Families! is a holiday home in Surfside Beach, with pool 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 $8,988.

From$1,284/night
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Sunny Days Will Leave You Smiling! Enjoy the pool and tennis courts! - Surfside Beach, MA

Sunny Days Will Leave You Smiling! Enjoy the pool and tennis courts!

Holiday Home, Surfside Beach

Sunny Days Will Leave You Smiling! Enjoy the pool and tennis courts! is a holiday home in Surfside Beach, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Sunny Days Will Leave You Smiling! Enjoy the pool and tennis courts!

Sunny Days Will Leave You Smiling! Enjoy the pool and tennis courts! is a holiday home in Surfside Beach, with pool 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 $9,695.

From$1,385/night
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Perfect Family Vacation Home! Heated Salt Water Pool - Car Ferry Tix Available - Surfside Beach, MA

Perfect Family Vacation Home! Heated Salt Water Pool - Car Ferry Tix Available

Holiday Home, Surfside Beach

Perfect Family Vacation Home! Heated Salt Water Pool - Car Ferry Tix Available is a holiday home in Surfside Beach, with pet-friendly space, pool access, and room for a group. This stay…

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About Perfect Family Vacation Home! Heated Salt Water Pool - Car Ferry Tix Available

Perfect Family Vacation Home! Heated Salt Water Pool - Car Ferry Tix Available is a holiday home in Surfside 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,222.

From$1,746/night
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Professionally Decorated Slice of Heaven-Near Beach w/ Pool, Tennis & Gym Access - Surfside Beach, MA

Professionally Decorated Slice of Heaven-Near Beach w/ Pool, Tennis & Gym Access

Holiday Home, Surfside Beach

Professionally Decorated Slice of Heaven-Near Beach w/ Pool, Tennis & Gym Access is a holiday home in Surfside Beach, with pool access, easy beach access, and kitchen access. This stay…

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About Professionally Decorated Slice of Heaven-Near Beach w/ Pool, Tennis & Gym Access

Professionally Decorated Slice of Heaven-Near Beach w/ Pool, Tennis & Gym Access is a holiday home in Surfside 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $13,209.

From$1,887/night
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Vacation rentals with parking in Surfside Beach, MA

Find vacation rentals that make arriving by car easier.

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant! - Surfside Beach, MA

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant!

Holiday Home, Surfside Beach

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant! is a holiday home in Surfside Beach, with easy beach access, parking, and kitchen access. This stay gives…

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About Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant!

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant! is a holiday home in Surfside 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,395.

From$1,056/night
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Classic Nantucket Charmer with Panoramic Dionis Views - Surfside Beach, MA

Classic Nantucket Charmer with Panoramic Dionis Views

Holiday Home, Surfside Beach

Classic Nantucket Charmer with Panoramic Dionis Views is a holiday home in Surfside Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Classic Nantucket Charmer with Panoramic Dionis Views

Classic Nantucket Charmer with Panoramic Dionis Views is a holiday home in Surfside 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 $8,619.

From$1,231/night
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Walk to Cisco/ Charming cottage and garage apt on Hummock Pond - Surfside Beach, MA

Walk to Cisco/ Charming cottage and garage apt on Hummock Pond

Cottage, Surfside Beach

Walk to Cisco/ Charming cottage and garage apt on Hummock Pond is a cottage in Surfside Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Walk to Cisco/ Charming cottage and garage apt on Hummock Pond

Walk to Cisco/ Charming cottage and garage apt on Hummock Pond is a cottage in Surfside 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,569.

From$1,510/night
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Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town - Surfside Beach, MA

Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town

Holiday Home, Surfside Beach

Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town is a holiday home in Surfside Beach, with easy beach access, parking, and kitchen access. This stay gives…

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About Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town

Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town is a holiday home in Surfside 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,191.

From$1,742/night
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Pet-friendly vacation rentals in Surfside Beach, MA

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

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl! - Surfside Beach, MA

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!

Holiday Home, Surfside Beach

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH · bikes & beach gear incl! is a holiday home in Surfside Beach, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH · bikes & beach gear incl! is a holiday home in Surfside 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 $5,397.

From$771/night
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Charming 2 Bedroom Cottage - Surfside Beach, MA

Charming 2 Bedroom Cottage

Cottage, Surfside Beach

Charming 2 Bedroom Cottage is a cottage in Surfside Beach, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming 2 Bedroom Cottage

Charming 2 Bedroom Cottage is a cottage in Surfside Beach, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,726.

From$961/night
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Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea - Surfside Beach, MA

Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea

Holiday Home, Surfside Beach

Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea is a holiday home in Surfside Beach, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable…

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About Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea

Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea is a holiday home in Surfside Beach, with pet-friendly space 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: pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,801.

From$1,114/night
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Perfect beach house for a great family vacation - Surfside Beach, MA

Perfect beach house for a great family vacation

Holiday Home, Surfside Beach

Perfect beach house for a great family vacation is a holiday home in Surfside Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Perfect beach house for a great family vacation

Perfect beach house for a great family vacation is a holiday home in Surfside 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 wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,622.

From$1,517/night
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Vacation rentals with a kitchen in Surfside Beach, MA

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

Never enough of Nantucket - Surfside Beach, MA

Never enough of Nantucket

Holiday Home, Surfside Beach

Never enough of Nantucket is a holiday home in Surfside Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Never enough of Nantucket

Never enough of Nantucket is a holiday home in Surfside 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,691.

From$956/night
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Nantucket Salty Nest- 3 bedroom 2.5 bathrooms in Tom Nevers. Sleep 7 - Surfside Beach, MA

Nantucket Salty Nest- 3 bedroom 2.5 bathrooms in Tom Nevers. Sleep 7

Holiday Home, Surfside Beach

Nantucket Salty Nest- 3 bedroom 2.5 bathrooms in Tom Nevers. Sleep 7 is a holiday home in Surfside Beach, with kitchen access and room for a group. This stay gives travelers a comfortable…

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About Nantucket Salty Nest- 3 bedroom 2.5 bathrooms in Tom Nevers. Sleep 7

Nantucket Salty Nest- 3 bedroom 2.5 bathrooms in Tom Nevers. Sleep 7 is a holiday home in Surfside Beach, with 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,124.

From$1,018/night
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Authentic Nantucket Experience at Sunny Daze! - Surfside Beach, MA

Authentic Nantucket Experience at Sunny Daze!

Holiday Home, Surfside Beach

Authentic Nantucket Experience at Sunny Daze! is a holiday home in Surfside Beach, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Authentic Nantucket Experience at Sunny Daze!

Authentic Nantucket Experience at Sunny Daze! is a holiday home in Surfside 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,355.

From$1,622/night
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Pond View Cottage- Luxury home near Miacomet beach - Surfside Beach, MA

Pond View Cottage- Luxury home near Miacomet beach

Holiday Home, Surfside Beach

Pond View Cottage- Luxury home near Miacomet beach is a holiday home in Surfside Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pond View Cottage- Luxury home near Miacomet beach

Pond View Cottage- Luxury home near Miacomet beach is a holiday home in Surfside 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $14,437.

From$2,062/night
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