Vacation rentals in South Shore, MA

89 available vacation rental offers

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Best vacation rentals and Airbnb offers in South Shore, MA

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport - South Shore, MA

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport

Apartment, South Shore

Tranquil 1 - Bedroom Retreat in Nantucket Near the Airport is a apartment in South Shore, 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 South Shore, 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! - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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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Custom Built Home on Private Lot in Fishers Landing - South Shore, MA

Custom Built Home on Private Lot in Fishers Landing

Holiday Home, South Shore

Custom Built Home on Private Lot in Fishers Landing is a holiday home in South Shore, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Custom Built Home on Private Lot in Fishers Landing

Custom Built Home on Private Lot in Fishers Landing is a holiday home in South Shore, 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 $4,974.

From$711/night
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WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl! - South Shore, MA

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

Holiday Home, South Shore

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH · bikes & beach gear incl! is a holiday home in South Shore, 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 South Shore, 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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Vacation rentals with a pool in South Shore, 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! - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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! - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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 - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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 - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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 South Shore, MA

Find vacation rentals that make arriving by car easier.

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant! - South Shore, MA

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

Holiday Home, South Shore

Enjoy beautiful Madaket beaches and sunsets, close to popular island restaurant! is a holiday home in South Shore, 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 South Shore, 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 - South Shore, MA

Classic Nantucket Charmer with Panoramic Dionis Views

Holiday Home, South Shore

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

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About Classic Nantucket Charmer with Panoramic Dionis Views

Classic Nantucket Charmer with Panoramic Dionis Views is a holiday home in South Shore, 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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Nantucket Loft w/ Harbor Views and walk to town - South Shore, MA

Nantucket Loft w/ Harbor Views and walk to town

Apartment, South Shore

Nantucket Loft w/ Harbor Views and walk to town is a apartment in South Shore, 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 South Shore, 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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Walk to Cisco/ Charming cottage and garage apt on Hummock Pond - South Shore, MA

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

Cottage, South Shore

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

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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 South Shore, 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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Pet-friendly vacation rentals in South Shore, MA

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

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

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

Holiday Home, South Shore

Madaket Beach House- Walk to Beach- Private Nantucket Home. is a holiday home in South Shore, 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 South Shore, 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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Charming 2 Bedroom Cottage - South Shore, MA

Charming 2 Bedroom Cottage

Cottage, South Shore

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

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About Charming 2 Bedroom Cottage

Charming 2 Bedroom Cottage is a cottage in South Shore, 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 - South Shore, MA

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

Holiday Home, South Shore

Monomoy Retreated- Nantucket’s Best Kept Secret Near Town and Sea is a holiday home in South Shore, 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 South Shore, 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 - South Shore, MA

Perfect beach house for a great family vacation

Holiday Home, South Shore

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

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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 South Shore, 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 South Shore, MA

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

Never enough of Nantucket - South Shore, MA

Never enough of Nantucket

Holiday Home, South Shore

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

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About Never enough of Nantucket

Never enough of Nantucket is a holiday home in South Shore, 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 - South Shore, MA

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

Holiday Home, South Shore

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

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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 South Shore, 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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Private Nantucket Cottage Walk to Surfside Beach - South Shore, MA

Private Nantucket Cottage Walk to Surfside Beach

Holiday Home, South Shore

Private Nantucket Cottage Walk to Surfside Beach is a holiday home in South Shore, 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 South Shore, 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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Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town - South Shore, MA

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

Holiday Home, South Shore

Luxurious Island Escape: Spacious, Ideally Located Near Surfside Beaches & Town is a holiday home in South Shore, 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 South Shore, 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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Family-friendly vacation rentals in South Shore, MA

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

Barn/cottage - South Shore, MA

Barn/cottage

Cottage, South Shore

Barn/cottage is a cottage in South Shore, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Barn/cottage

Barn/cottage is a cottage in South Shore, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: non smoking, adult only, pets::not allowed, and pets not allowed.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,195.

From$599/night
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Tom Nevers-Family neighborhood - South Shore, MA

Tom Nevers-Family neighborhood

Holiday Home, South Shore

Tom Nevers-Family neighborhood is a holiday home in South Shore, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Tom Nevers-Family neighborhood

Tom Nevers-Family neighborhood is a holiday home in South Shore, 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 $5,806.

From$829/night
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Sweeping unobstructed views, family friendly, great value. - South Shore, MA

Sweeping unobstructed views, family friendly, great value.

Holiday Home, South Shore

Sweeping unobstructed views, family friendly, great value. is a holiday home in South Shore, with room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Sweeping unobstructed views, family friendly, great value.

Sweeping unobstructed views, family friendly, great value. is a holiday home in South Shore, 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: washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,018.

From$860/night
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Charming Historic Downtown Cottage - South Shore, MA

Charming Historic Downtown Cottage

Cottage, South Shore

Charming Historic Downtown Cottage is a cottage in South Shore, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Historic Downtown Cottage

Charming Historic Downtown Cottage is a cottage in South Shore, 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 $7,168.

From$1,024/night
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