Vacation rentals in Bailey Island, ME

112 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Bailey Island, ME

Cozy Efficiency with Beautiful Ocean Views - Bailey Island, ME

Cozy Efficiency with Beautiful Ocean Views

Apartment, Bailey Island

Cozy Efficiency with Beautiful Ocean Views is a apartment in Bailey Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Efficiency with Beautiful Ocean Views

Cozy Efficiency with Beautiful Ocean Views is a apartment in Bailey Island, 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 $1,277.

From$125/night
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Henry's HideaWay Harpswell - Bailey Island, ME

Henry's HideaWay Harpswell

Cottage, Bailey Island

Henry's HideaWay Harpswell is a cottage in Bailey Island, 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 Henry's HideaWay Harpswell

Henry's HideaWay Harpswell is a cottage in Bailey Island, 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 $1,208.

From$140/night
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! Enjoy beautiful Orr's Island. . - Bailey Island, ME

! Enjoy beautiful Orr's Island. .

Holiday Home, Bailey Island

! Enjoy beautiful Orr's Island. . is a holiday home in Bailey Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About ! Enjoy beautiful Orr's Island. .

! Enjoy beautiful Orr's Island. . is a holiday home in Bailey Island, 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 $1,622.

From$175/night
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Don't miss this charming studio overlooking Quahog Bay in scenic Harpswell! - Bailey Island, ME

Don't miss this charming studio overlooking Quahog Bay in scenic Harpswell!

Apartment, Bailey Island

Don't miss this charming studio overlooking Quahog Bay in scenic Harpswell! is a apartment in Bailey Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Don't miss this charming studio overlooking Quahog Bay in scenic Harpswell!

Don't miss this charming studio overlooking Quahog Bay in scenic Harpswell! is a apartment in Bailey Island, 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 $1,556.

From$176/night
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Browse Waterfront Vacation Rentals in Bailey Island, ME

Discover vacation rentals close to the coast, water, and beach areas around Bailey Island, ME.

This spacious 2nd floor garage apartment offers phenomenal open ocean views! - Bailey Island, ME

This spacious 2nd floor garage apartment offers phenomenal open ocean views!

Apartment, Bailey Island

This spacious 2nd floor garage apartment offers phenomenal open ocean views! is a apartment in Bailey Island, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About This spacious 2nd floor garage apartment offers phenomenal open ocean views!

This spacious 2nd floor garage apartment offers phenomenal open ocean views! is a apartment in Bailey Island, 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 $3,182.

From$356/night
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NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access - Bailey Island, ME

NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access

Holiday Home, Bailey Island

NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access is a holiday home in Bailey Island, with easy beach access, parking, and kitchen access. This stay gives…

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About NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access

NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access is a holiday home in Bailey Island, 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 $3,662.

From$385/night
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Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~ - Bailey Island, ME

Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~

Cottage, Bailey Island

Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~ is a cottage in Bailey Island, with easy beach access, outdoor space, and kitchen access. This stay gives…

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About Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~

Step off the deck to enjoy the beach & a short walk down the scenic peninsula ~ is a cottage in Bailey Island, with easy beach access, outdoor 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, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,262.

From$427/night
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Gorgeous ocean views with private beach access. - Bailey Island, ME

Gorgeous ocean views with private beach access.

Holiday Home, Bailey Island

Gorgeous ocean views with private beach access. is a holiday home in Bailey Island, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Gorgeous ocean views with private beach access.

Gorgeous ocean views with private beach access. is a holiday home in Bailey Island, 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, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,370.

From$473/night
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Browse Vacation Rentals with a Pool in Bailey Island, ME

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

The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon... - Bailey Island, ME

The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon...

Cottage, Bailey Island

The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon... is a cottage in Bailey Island, with pet-friendly space and pool access. This stay gives…

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About The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon...

The Auburn Colony is for the vacationer who wants to tap into the history and traditions of colon... is a cottage in Bailey Island, with pet-friendly space and pool 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 $5,235.

From$491/night
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Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets - Bailey Island, ME

Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets

Holiday Home, Bailey Island

Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets is a holiday home in Bailey Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets

Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets is a holiday home in Bailey Island, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,955.

From$540/night
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Coastal, 3 bedroom, 2 bath home with pool! - Bailey Island, ME

Coastal, 3 bedroom, 2 bath home with pool!

Holiday Home, Bailey Island

Coastal, 3 bedroom, 2 bath home with pool! is a holiday home in Bailey Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Coastal, 3 bedroom, 2 bath home with pool!

Coastal, 3 bedroom, 2 bath home with pool! is a holiday home in Bailey Island, with pool 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,026.

From$720/night
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Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage. - Bailey Island, ME

Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage.

Holiday Home, Bailey Island

Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage. is a holiday home in Bailey Island, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage.

Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage. is a holiday home in Bailey Island, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,240.

From$800/night
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Best Bailey Island, ME vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor - Bailey Island, ME

Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor

Holiday Home, Bailey Island

Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor is a holiday home in Bailey Island, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor

Welcome to Harbor Heights- your cozy coastal getaway in Cundy's Harbor is a holiday home in Bailey Island, 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 $1,528.

From$158/night
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Peaceful, Rustic Old Town Cabin Harpswell Getaway - Bailey Island, ME

Peaceful, Rustic Old Town Cabin Harpswell Getaway

Cabin, Bailey Island

Peaceful, Rustic Old Town Cabin Harpswell Getaway is a cabin in Bailey Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peaceful, Rustic Old Town Cabin Harpswell Getaway

Peaceful, Rustic Old Town Cabin Harpswell Getaway is a cabin in Bailey Island, 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 $1,663.

From$159/night
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Luxury Waterfront Tiny House - Bailey Island, ME

Luxury Waterfront Tiny House

Holiday Home, Bailey Island

Luxury Waterfront Tiny House is a holiday home in Bailey Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury Waterfront Tiny House

Luxury Waterfront Tiny House is a holiday home in Bailey Island, 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 $1,622.

From$173/night
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Cozy, 2nd Floor Studio on Mere Point - Bailey Island, ME

Cozy, 2nd Floor Studio on Mere Point

Apartment, Bailey Island

Cozy, 2nd Floor Studio on Mere Point is a apartment in Bailey Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy, 2nd Floor Studio on Mere Point

Cozy, 2nd Floor Studio on Mere Point is a apartment in Bailey Island, 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 $2,064.

From$225/night
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Best Pet-Friendly Vacation Rentals in Bailey Island, ME

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

Unique Waterfront Experience - Bailey Island, ME

Unique Waterfront Experience

Holiday Home, Bailey Island

Unique Waterfront Experience is a holiday home in Bailey Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Unique Waterfront Experience

Unique Waterfront Experience is a holiday home in Bailey Island, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,620.

From$275/night
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Historic Pumpkin House located in West Harpswell - Bailey Island, ME

Historic Pumpkin House located in West Harpswell

Holiday Home, Bailey Island

Historic Pumpkin House located in West Harpswell is a holiday home in Bailey Island, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Historic Pumpkin House located in West Harpswell

Historic Pumpkin House located in West Harpswell is a holiday home in Bailey Island, 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: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,777.

From$288/night
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Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views. - Bailey Island, ME

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.

Holiday Home, Bailey Island

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views. is a holiday home in Bailey Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views. is a holiday home in Bailey Island, 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 $2,907.

From$317/night
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Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home. - Bailey Island, ME

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Holiday Home, Bailey Island

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home. is a holiday home in Bailey Island, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home. is a holiday home in Bailey Island, 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 $3,643.

From$367/night
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Best Bailey Island, ME vacation rentals with a kitchen

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

~Maine Glamping at its Finest~ - Bailey Island, ME

~Maine Glamping at its Finest~

Apartment, Bailey Island

~Maine Glamping at its Finest~ is a apartment in Bailey Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About ~Maine Glamping at its Finest~

~Maine Glamping at its Finest~ is a apartment in Bailey Island, 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,888.

From$204/night
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Beautiful Oceanfront Apartment, scenic views and water access - Bailey Island, ME

Beautiful Oceanfront Apartment, scenic views and water access

Apartment, Bailey Island

Beautiful Oceanfront Apartment, scenic views and water access is a apartment in Bailey Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Beautiful Oceanfront Apartment, scenic views and water access

Beautiful Oceanfront Apartment, scenic views and water access is a apartment in Bailey Island, 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 $2,137.

From$231/night
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Bay Haven. Comfort, deck & water access. - Bailey Island, ME

Bay Haven. Comfort, deck & water access.

Holiday Home, Bailey Island

Bay Haven. Comfort, deck & water access. is a holiday home in Bailey Island, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Bay Haven. Comfort, deck & water access.

Bay Haven. Comfort, deck & water access. is a holiday home in Bailey Island, with easy beach access, 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, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,357.

From$441/night
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Barnacle - quiet family Maine waterfront getaway - Bailey Island, ME

Barnacle - quiet family Maine waterfront getaway

Cabin, Bailey Island

Barnacle - quiet family Maine waterfront getaway is a cabin in Bailey Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Barnacle - quiet family Maine waterfront getaway

Barnacle - quiet family Maine waterfront getaway is a cabin in Bailey Island, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,119.

From$471/night
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