Vacation rentals in Kent Island Estates, MD

61 available vacation rental offers

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Best vacation rentals and Airbnb offers in Kent Island Estates, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Kent Island Estates, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Kent Island Estates

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island Estates, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island Estates, with easy beach access, parking, 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,684.

From$150/night
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'callaway Drive Retreat' 3BR Home Near Water - Kent Island Estates, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Kent Island Estates

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Kent Island Estates, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base…

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Kent Island Estates, with kitchen access, 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, free wifi, kitchen, with kitchen, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$184/night
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Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Kent Island Estates, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Kent Island Estates

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island Estates, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island Estates, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,520.

From$217/night
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Studio Apartment in Downtown Annapolis - Kent Island Estates, MD

Studio Apartment in Downtown Annapolis

Apartment, Kent Island Estates

Studio Apartment in Downtown Annapolis is a apartment in Kent Island Estates, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Studio Apartment in Downtown Annapolis

Studio Apartment in Downtown Annapolis is a apartment in Kent Island Estates, 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 cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,686.

From$241/night
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Waterfront vacation rentals in Kent Island Estates, MD

Discover vacation rentals close to the coast, water, and beach areas around Kent Island Estates, MD.

Edgewater's Shelby on the Bay - Kent Island Estates, MD

Edgewater's Shelby on the Bay

Holiday Home, Kent Island Estates

Edgewater's Shelby on the Bay is a holiday home in Kent Island Estates, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Edgewater's Shelby on the Bay

Edgewater's Shelby on the Bay is a holiday home in Kent Island Estates, 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 onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,374.

From$482/night
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Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. - Kent Island Estates, MD

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Holiday Home, Kent Island Estates

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. is a holiday home in Kent Island Estates, with easy beach access, kitchen access, and a quieter setting. This…

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About Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. is a holiday home in Kent Island Estates, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,192.

From$599/night
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Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails - Kent Island Estates, MD

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Holiday Home, Kent Island Estates

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails is a holiday home in Kent Island Estates, with easy beach access, parking, and kitchen access. This stay gives…

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About Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails

Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails is a holiday home in Kent Island Estates, 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 $4,626.

From$661/night
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Charming 3 Bedroom 3 Bath Beach Front Property - Kent Island Estates, MD

Charming 3 Bedroom 3 Bath Beach Front Property

Holiday Home, Kent Island Estates

Charming 3 Bedroom 3 Bath Beach Front Property is a holiday home in Kent Island Estates, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Charming 3 Bedroom 3 Bath Beach Front Property

Charming 3 Bedroom 3 Bath Beach Front Property is a holiday home in Kent Island Estates, 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, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,706.

From$672/night
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Vacation rentals with a pool in Kent Island Estates, MD

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

Eastern Shore Waterside Cottage Near St. Michaels - Kent Island Estates, MD

Eastern Shore Waterside Cottage Near St. Michaels

Cottage, Kent Island Estates

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in Kent Island Estates, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels is a cottage in Kent Island Estates, 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,847.

From$407/night
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Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - Kent Island Estates, MD

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Holiday Home, Kent Island Estates

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Kent Island Estates, with pet-friendly space and pool access. This stay gives travelers…

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About Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels · Private Dock · Kayaks Bikes · Pet Friendly is a holiday home in Kent Island Estates, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,065.

From$724/night
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock - Kent Island Estates, MD

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Holiday Home, Kent Island Estates

Minutes from Downtown St. Michaels · Pool · Hot Tub · Private Dock is a holiday home in Kent Island Estates, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels · Pool · Hot Tub · Private Dock is a holiday home in Kent Island Estates, 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: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,430.

From$919/night
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Chesapeake Bay Waterfront ARTectural Home - Kent Island Estates, MD

Chesapeake Bay Waterfront ARTectural Home

Holiday Home, Kent Island Estates

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Kent Island Estates, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Chesapeake Bay Waterfront ARTectural Home

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Kent Island Estates, with 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,130.

From$1,161/night
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Vacation rentals with parking in Kent Island Estates, MD

Find vacation rentals that make arriving by car easier.

2BR Historic District Gem w/Parking Near City Dock - Kent Island Estates, MD

2BR Historic District Gem w/Parking Near City Dock

Holiday Home, Kent Island Estates

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Kent Island Estates, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About 2BR Historic District Gem w/Parking Near City Dock

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Kent Island Estates, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,785.

From$398/night
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Enchanting West River Retreat - Kent Island Estates, MD

Enchanting West River Retreat

Cottage, Kent Island Estates

Enchanting West River Retreat is a cottage in Kent Island Estates, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Enchanting West River Retreat

Enchanting West River Retreat is a cottage in Kent Island Estates, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,905.

From$415/night
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Port of Call: 5BR Modern Nautical Luxury - Kent Island Estates, MD

Port of Call: 5BR Modern Nautical Luxury

Holiday Home, Kent Island Estates

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Kent Island Estates, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Port of Call: 5BR Modern Nautical Luxury

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Kent Island Estates, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,513.

From$502/night
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The Snuggery Inn & Suites Captain`s Quarters - Kent Island Estates, MD

The Snuggery Inn & Suites Captain`s Quarters

B & B, Kent Island Estates

The Snuggery Inn & Suites Captain`s Quarters is a b & b in Kent Island Estates, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Snuggery Inn & Suites Captain`s Quarters

The Snuggery Inn & Suites Captain`s Quarters is a b & b in Kent Island Estates, 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 wifi, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,237.

From$462/night
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Pet-friendly vacation rentals in Kent Island Estates, MD

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

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Kent Island Estates, MD

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Apartment, Kent Island Estates

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Kent Island Estates, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Kent Island Estates, 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 $1,334.

From$191/night
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Lovely bay views with kayaks, bikes, fire pit, crabbing & more - Kent Island Estates, MD

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Holiday Home, Kent Island Estates

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Kent Island Estates, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Kent Island Estates, 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 $2,075.

From$296/night
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Family Home on Mayo Peninsula | Deck | Sleeps 10 - Kent Island Estates, MD

Family Home on Mayo Peninsula | Deck | Sleeps 10

Holiday Home, Kent Island Estates

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Kent Island Estates, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base…

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About Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Kent Island Estates, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,579.

From$368/night
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5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking - Kent Island Estates, MD

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Holiday Home, Kent Island Estates

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking is a holiday home in Kent Island Estates, with pet-friendly space, easy beach access, and parking. This stay…

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About 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking is a holiday home in Kent Island Estates, 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, washer, and dryer.

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

From$824/night
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Vacation rentals with a kitchen in Kent Island Estates, MD

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

Minutes from Downtown St. Michaels | Character Filled - Kent Island Estates, MD

Minutes from Downtown St. Michaels | Character Filled

Holiday Home, Kent Island Estates

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Kent Island Estates, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Minutes from Downtown St. Michaels | Character Filled

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Kent Island Estates, 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 $2,610.

From$373/night
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining - Kent Island Estates, MD

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

Holiday Home, Kent Island Estates

Minutes from Downtown St. Michaels and Tilghman · Private Dock · Outdoor Dining is a holiday home in Kent Island Estates, with parking and kitchen access. This stay gives travelers a…

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About Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

Minutes from Downtown St. Michaels and Tilghman · Private Dock · Outdoor Dining is a holiday home in Kent Island Estates, 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 $3,746.

From$535/night
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Ahoy! Game Room, Screened Porch, Yard Mins to DTA - Kent Island Estates, MD

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Holiday Home, Kent Island Estates

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Kent Island Estates, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Kent Island Estates, 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 $3,829.

From$547/night
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Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach - Kent Island Estates, MD

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home, Kent Island Estates

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Kent Island Estates, with pet-friendly space, easy beach access, and kitchen access. This…

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About Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Kent Island Estates, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,630.

From$661/night
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