Vacation rentals in Hillsmere Shores, MD

66 available vacation rental offers

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Best vacation rentals and Airbnb offers in Hillsmere Shores, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Hillsmere Shores, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Hillsmere Shores

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

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,684.

From$150/night
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Charming 1-bedroom cottage with AC in cozy Harwood - Hillsmere Shores, MD

Charming 1-bedroom cottage with AC in cozy Harwood

Cottage, Hillsmere Shores

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Hillsmere Shores, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Hillsmere Shores, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,337.

From$191/night
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Studio Apartment in Downtown Annapolis - Hillsmere Shores, MD

Studio Apartment in Downtown Annapolis

Apartment, Hillsmere Shores

Studio Apartment in Downtown Annapolis is a apartment in Hillsmere Shores, 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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,735.

From$248/night
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Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA. - Hillsmere Shores, MD

Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.

Apartment, Hillsmere Shores

Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA. is a apartment in Hillsmere Shores. This stay gives travelers a comfortable base for exploring the area,…

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About Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA.

Custom Studio Efficiency apartment with AC easy accces to Annapolis and USNA. is a apartment in Hillsmere Shores. 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, ac, air conditioning, heating, and internet.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,959.

From$280/night
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Family-friendly vacation rentals in Hillsmere Shores, MD

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

'callaway Drive Retreat' 3BR Home Near Water - Hillsmere Shores, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Hillsmere Shores

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

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,747.

From$184/night
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Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK - Hillsmere Shores, MD

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Cottage, Hillsmere Shores

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Hillsmere Shores, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK is a cottage in Hillsmere Shores, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,328.

From$333/night
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Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach - Hillsmere Shores, MD

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

Holiday Home, Hillsmere Shores

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

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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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,630.

From$661/night
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Adorable cottage! Walking distance to USNA & downtown! (VRBO only) - Hillsmere Shores, MD

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Holiday Home, Hillsmere Shores

Adorable cottage! Walking distance to USNA & downtown! (VRBO only) is a holiday home in Hillsmere Shores, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Adorable cottage! Walking distance to USNA & downtown! (VRBO only) is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,654.

From$665/night
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Pet-friendly vacation rentals in Hillsmere Shores, 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 - Hillsmere Shores, MD

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

Apartment, Hillsmere Shores

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

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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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,329.

From$190/night
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Lovely bay views with kayaks, bikes, fire pit, crabbing & more - Hillsmere Shores, MD

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

Holiday Home, Hillsmere Shores

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Hillsmere Shores, 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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,079.

From$297/night
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Pet Friendly Hideaway for 4 Close to Annapolis - Hillsmere Shores, MD

Pet Friendly Hideaway for 4 Close to Annapolis

Holiday Home, Hillsmere Shores

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Hillsmere Shores, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pet Friendly Hideaway for 4 Close to Annapolis

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Hillsmere Shores, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,563.

From$366/night
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Ahoy! Game Room, Screened Porch, Yard Mins to DTA - Hillsmere Shores, MD

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

Holiday Home, Hillsmere Shores

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Hillsmere Shores, 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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,260.

From$609/night
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Vacation rentals with a pool in Hillsmere Shores, MD

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

Pool Loft Suite | Bay Access & Beach Passes - Hillsmere Shores, MD

Pool Loft Suite | Bay Access & Beach Passes

Apartment, Hillsmere Shores

Pool Loft Suite · Bay Access & Beach Passes is a apartment in Hillsmere Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite · Bay Access & Beach Passes is a apartment in Hillsmere Shores, with pool access, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,002.

From$286/night
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Annapolis Home | Fenced Yard | Pool Table | 10 Guests - Hillsmere Shores, MD

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Holiday Home, Hillsmere Shores

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Hillsmere Shores, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base…

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About Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Hillsmere Shores, with pet-friendly space, pool 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,297.

From$471/night
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42 Acres of Serenity & Nature Just 15 Miles To Annapolis - Hillsmere Shores, MD

42 Acres of Serenity & Nature Just 15 Miles To Annapolis

Holiday Home, Hillsmere Shores

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Hillsmere Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About 42 Acres of Serenity & Nature Just 15 Miles To Annapolis

42 Acres of Serenity & Nature Just 15 Miles To Annapolis is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $6,917.

From$988/night
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The Inn at Tacaro Estate - Hillsmere Shores, MD

The Inn at Tacaro Estate

B & B, Hillsmere Shores

The Inn at Tacaro Estate is a b & b in Hillsmere Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Inn at Tacaro Estate

The Inn at Tacaro Estate is a b & b in Hillsmere Shores, with 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, free breakfast, pool, hot tub, and free wifi.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,583.

From$449/night
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Vacation rentals with parking in Hillsmere Shores, MD

Find vacation rentals that make arriving by car easier.

Cozy 1-bedroom studio in pleasant Crofton with AC - Hillsmere Shores, MD

Cozy 1-bedroom studio in pleasant Crofton with AC

Apartment, Hillsmere Shores

Cozy 1-bedroom studio in pleasant Crofton with AC is a apartment in Hillsmere Shores, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 1-bedroom studio in pleasant Crofton with AC

Cozy 1-bedroom studio in pleasant Crofton with AC is a apartment in Hillsmere Shores, 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, gym, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $978.

From$140/night
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Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. - Hillsmere Shores, MD

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Guest House, Hillsmere Shores

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Hillsmere Shores, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,617.

From$231/night
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Relax on Kent Island in a 4 Bedroom Home w/Waterview! - Hillsmere Shores, MD

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home, Hillsmere Shores

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Hillsmere Shores, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,378.

From$340/night
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Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. - Hillsmere Shores, MD

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Apartment, Hillsmere Shores

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. is a apartment in Hillsmere Shores, with easy beach access and parking. This stay gives travelers a comfortable base…

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About Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. is a apartment in Hillsmere Shores, with 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, parking, free parking, ac, and air conditioning.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,798.

From$400/night
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Vacation rentals with a kitchen in Hillsmere Shores, MD

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

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Hillsmere Shores, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Hillsmere Shores

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

Read more

About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,520.

From$217/night
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Chic 3 BR / 2 BA Cottage Near Chesapeake Bay - Hillsmere Shores, MD

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Home, Hillsmere Shores

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in Hillsmere Shores, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay is a holiday home in Hillsmere Shores, with easy beach access, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,420.

From$346/night
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Enchanting West River Retreat - Hillsmere Shores, MD

Enchanting West River Retreat

Cottage, Hillsmere Shores

Enchanting West River Retreat is a cottage in Hillsmere Shores, 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 Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,905.

From$415/night
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Renovated 3BR | Near Sandy Point Beach - Hillsmere Shores, MD

Renovated 3BR | Near Sandy Point Beach

Holiday Home, Hillsmere Shores

Renovated 3BR · Near Sandy Point Beach is a holiday home in Hillsmere Shores, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Renovated 3BR | Near Sandy Point Beach

Renovated 3BR · Near Sandy Point Beach is a holiday home in Hillsmere Shores, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,139.

From$448/night
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