Vacation rentals in Chebeague Island, ME

103 available vacation rental offers

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Best vacation rentals and Airbnb offers in Chebeague Island, ME

Henry's HideaWay Harpswell - Chebeague Island, ME

Henry's HideaWay Harpswell

Cottage, Chebeague Island

Henry's HideaWay Harpswell is a cottage in Chebeague Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Henry's HideaWay Harpswell

Henry's HideaWay Harpswell is a cottage in Chebeague 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 $1,108.

From$158/night
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Cozy Efficiency with Beautiful Ocean Views - Chebeague Island, ME

Cozy Efficiency with Beautiful Ocean Views

Apartment, Chebeague Island

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

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About Cozy Efficiency with Beautiful Ocean Views

Cozy Efficiency with Beautiful Ocean Views is a apartment in Chebeague 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 $1,172.

From$167/night
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! Enjoy beautiful Orr's Island. . - Chebeague Island, ME

! Enjoy beautiful Orr's Island. .

Holiday Home, Chebeague Island

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

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About ! Enjoy beautiful Orr's Island. .

! Enjoy beautiful Orr's Island. . is a holiday home in Chebeague 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 $1,488.

From$213/night
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Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove - Chebeague Island, ME

Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove

Cottage, Chebeague Island

Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove is a cottage in Chebeague Island, with parking, kitchen access, and room for a group. This stay gives travelers…

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About Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove

Lowell's Cove Cottage - Quaint 2BR Cottage short walk away from Lowell's Cove is a cottage in Chebeague Island, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,726.

From$247/night
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Waterfront vacation rentals in Chebeague Island, ME

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

Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation! - Chebeague Island, ME

Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation!

Cottage, Chebeague Island

Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation! is a cottage in Chebeague Island, with easy beach access and kitchen access. This stay gives travelers a…

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About Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation!

Oceanside Cottage On A Beautiful Private Beach - Enjoy Your Maine Vacation! is a cottage in Chebeague 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 cancellation, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,650.

From$379/night
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Modern Waterfront Apt with Bay Views - Chebeague Island, ME

Modern Waterfront Apt with Bay Views

Apartment, Chebeague Island

Modern Waterfront Apt with Bay Views is a apartment in Chebeague Island, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Waterfront Apt with Bay Views

Modern Waterfront Apt with Bay Views is a apartment in Chebeague 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 cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,749.

From$393/night
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This spacious 2nd floor garage apartment offers phenomenal open ocean views! - Chebeague Island, ME

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

Apartment, Chebeague Island

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

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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 Chebeague 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 $2,854.

From$408/night
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NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access - Chebeague Island, ME

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

Holiday Home, Chebeague Island

NEW Tranquil Tides - 2-bedroom home with privacy, AC and tidal waterfront access is a holiday home in Chebeague 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 Chebeague 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 $3,367.

From$481/night
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Vacation rentals with a pool in Chebeague 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... - Chebeague Island, ME

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

Cottage, Chebeague Island

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

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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 Chebeague 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 $4,802.

From$686/night
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Coastal, 3 bedroom, 2 bath home with pool! - Chebeague Island, ME

Coastal, 3 bedroom, 2 bath home with pool!

Holiday Home, Chebeague Island

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

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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 Chebeague 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 $5,965.

From$852/night
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Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage. - Chebeague Island, ME

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

Holiday Home, Chebeague Island

Maine Coast Experience. Full 180 Degree Ocean View. 275ft of frontage. is a holiday home in Chebeague 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 Chebeague 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 $6,642.

From$949/night
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Vacation rentals with parking in Chebeague Island, ME

Find vacation rentals that make arriving by car easier.

The Orchard House: Inn & Cafe - Chebeague Island, ME

The Orchard House: Inn & Cafe

B & B, Chebeague Island

The Orchard House: Inn & Cafe is a b & b in Chebeague Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Orchard House: Inn & Cafe

The Orchard House: Inn & Cafe is a b & b in Chebeague Island, with 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, free breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,768.

From$232/night
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Private 1st Floor Studio in Victorian Home - Steps to LL Bean, Downtown Freeport - Chebeague Island, ME

Private 1st Floor Studio in Victorian Home - Steps to LL Bean, Downtown Freeport

Holiday Home, Chebeague Island

Private 1st Floor Studio in Victorian Home - Steps to LL Bean, Downtown Freeport is a holiday home in Chebeague Island, with parking and kitchen access. This stay gives travelers a…

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About Private 1st Floor Studio in Victorian Home - Steps to LL Bean, Downtown Freeport

Private 1st Floor Studio in Victorian Home - Steps to LL Bean, Downtown Freeport is a holiday home in Chebeague 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 $1,777.

From$254/night
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Cozy, 2nd Floor Studio on Mere Point - Chebeague Island, ME

Cozy, 2nd Floor Studio on Mere Point

Apartment, Chebeague Island

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

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About Cozy, 2nd Floor Studio on Mere Point

Cozy, 2nd Floor Studio on Mere Point is a apartment in Chebeague 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 $1,894.

From$271/night
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The Kendall Inn - Chebeague Island, ME

The Kendall Inn

B & B, Chebeague Island

The Kendall Inn is a b & b in Chebeague Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About The Kendall Inn

The Kendall Inn is a b & b in Chebeague Island, with 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, free breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,793.

From$235/night
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Pet-friendly vacation rentals in Chebeague Island, ME

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

Spacious 1-Bedroom Apartment With Gorgeous Yard! - Chebeague Island, ME

Spacious 1-Bedroom Apartment With Gorgeous Yard!

Apartment, Chebeague Island

Spacious 1-Bedroom Apartment With Gorgeous Yard! is a apartment in Chebeague Island, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Spacious 1-Bedroom Apartment With Gorgeous Yard!

Spacious 1-Bedroom Apartment With Gorgeous Yard! is a apartment in Chebeague Island, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,353.

From$336/night
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Charming 3BR, 2.5BA Pet-friendly home, Ocean access just a short walk away - Chebeague Island, ME

Charming 3BR, 2.5BA Pet-friendly home, Ocean access just a short walk away

Holiday Home, Chebeague Island

Charming 3BR, 2.5BA Pet-friendly home, Ocean access just a short walk away is a holiday home in Chebeague Island, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Charming 3BR, 2.5BA Pet-friendly home, Ocean access just a short walk away

Charming 3BR, 2.5BA Pet-friendly home, Ocean access just a short walk away is a holiday home in Chebeague 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 $2,485.

From$355/night
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Historic Pumpkin House located in West Harpswell - Chebeague Island, ME

Historic Pumpkin House located in West Harpswell

Holiday Home, Chebeague Island

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

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About Historic Pumpkin House located in West Harpswell

Historic Pumpkin House located in West Harpswell is a holiday home in Chebeague 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 $2,549.

From$364/night
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Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views. - Chebeague Island, ME

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.

Holiday Home, Chebeague Island

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views. is a holiday home in Chebeague 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 Chebeague 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 $2,583.

From$369/night
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Vacation rentals with a kitchen in Chebeague Island, ME

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

Cozy Studio in Downtown Freeport - Chebeague Island, ME

Cozy Studio in Downtown Freeport

Apartment, Chebeague Island

Cozy Studio in Downtown Freeport is a apartment in Chebeague 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 Studio in Downtown Freeport

Cozy Studio in Downtown Freeport is a apartment in Chebeague 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,827.

From$261/night
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The Bow Street Abode / Charming 2 BR Retreat - Chebeague Island, ME

The Bow Street Abode / Charming 2 BR Retreat

Apartment, Chebeague Island

The Bow Street Abode / Charming 2 BR Retreat is a apartment in Chebeague Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About The Bow Street Abode / Charming 2 BR Retreat

The Bow Street Abode / Charming 2 BR Retreat is a apartment in Chebeague Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,067.

From$295/night
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Authentic maine cottage with direct water frontage - Chebeague Island, ME

Authentic maine cottage with direct water frontage

Cottage, Chebeague Island

Authentic maine cottage with direct water frontage is a cottage in Chebeague Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Authentic maine cottage with direct water frontage

Authentic maine cottage with direct water frontage is a cottage in Chebeague 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,518.

From$360/night
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Summer Cottage - Chebeague Island, ME

Summer Cottage

Cottage, Chebeague Island

Summer Cottage is a cottage in Chebeague Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Summer Cottage

Summer Cottage is a cottage in Chebeague Island, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,611.

From$373/night
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