Vacation rentals in Dorchester County, MD

44 available vacation rental offers

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Best vacation rentals and Airbnb offers in Dorchester County, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD - Dorchester County, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD

Condo, Dorchester County

Station House East: Upscale Loft in the Historic District Cambridge, MD is a condo in Dorchester County, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD is a condo in Dorchester County, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,352.

From$193/night
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La Casa Azul . with Wi-Fi, AC - Dorchester County, MD

La Casa Azul . with Wi-Fi, AC

Holiday Home, Dorchester County

La Casa Azul . with Wi-Fi, AC is a holiday home in Dorchester County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About La Casa Azul . with Wi-Fi, AC

La Casa Azul . with Wi-Fi, AC is a holiday home in Dorchester County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$196/night
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Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people - Dorchester County, MD

Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people

Holiday Home, Dorchester County

Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people is a holiday home in Dorchester County, with pet-friendly space, outdoor space, and kitchen access. This stay gives…

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About Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people

Quarterdeck cottage at Swan Cove Manor - A cozy stay for up to 4 people is a holiday home in Dorchester County, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,512.

From$216/night
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Waterfront Cottage in Beautiful Hoopers Island - Dorchester County, MD

Waterfront Cottage in Beautiful Hoopers Island

Cottage, Dorchester County

Waterfront Cottage in Beautiful Hoopers Island is a cottage in Dorchester County, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island is a cottage in Dorchester County, 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 $1,706.

From$244/night
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Vacation rentals with a pool in Dorchester County, MD

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

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! - Dorchester County, MD

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Apartment, Dorchester County

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! is a apartment in Dorchester County, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About < 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! is a apartment in Dorchester County, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,649.

From$436/night
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< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! - Dorchester County, MD

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Holiday Home, Dorchester County

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! is a holiday home in Dorchester County, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About < 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! is a holiday home in Dorchester County, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,089.

From$441/night
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Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD - Dorchester County, MD

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

Holiday Home, Dorchester County

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD is a holiday home in Dorchester County, with pool access, easy beach access, and parking. This stay gives…

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About Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD

Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD is a holiday home in Dorchester County, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,910.

From$559/night
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Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball - Dorchester County, MD

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Country House, Dorchester County

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball is a country house in Dorchester County, with pool access, easy beach access, and kitchen access. This stay…

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About Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball is a country house in Dorchester County, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,963.

From$709/night
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Vacation rentals with parking in Dorchester County, MD

Find vacation rentals that make arriving by car easier.

Riverside Lodge Bed & Breakfast on the Honga River UNIT E - Dorchester County, MD

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Holiday Home, Dorchester County

Riverside Lodge Bed & Breakfast on the Honga River UNIT E is a holiday home in Dorchester County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E is a holiday home in Dorchester County, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,016.

From$288/night
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Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland - Dorchester County, MD

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Condo, Dorchester County

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland is a condo in Dorchester County, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland is a condo in Dorchester County, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,164.

From$452/night
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Attractive Waterfront Home over looking Choptank River. Sleeps 5 - Dorchester County, MD

Attractive Waterfront Home over looking Choptank River. Sleeps 5

Holiday Home, Dorchester County

Attractive Waterfront Home over looking Choptank River. Sleeps 5 is a holiday home in Dorchester County, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Attractive Waterfront Home over looking Choptank River. Sleeps 5

Attractive Waterfront Home over looking Choptank River. Sleeps 5 is a holiday home in Dorchester County, 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 $3,386.

From$484/night
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Riverside Lodge Bed & Breakfast on the Honga River UNIT B - Dorchester County, MD

Riverside Lodge Bed & Breakfast on the Honga River UNIT B

B & B, Dorchester County

Riverside Lodge Bed & Breakfast on the Honga River UNIT B is a b & b in Dorchester County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Riverside Lodge Bed & Breakfast on the Honga River UNIT B

Riverside Lodge Bed & Breakfast on the Honga River UNIT B is a b & b in Dorchester County, 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 $2,016.

From$288/night
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Pet-friendly vacation rentals in Dorchester County, MD

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

Cozy River House in the Historic District of Cambridge, MD - Dorchester County, MD

Cozy River House in the Historic District of Cambridge, MD

Holiday Home, Dorchester County

Cozy River House in the Historic District of Cambridge, MD is a holiday home in Dorchester County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Cozy River House in the Historic District of Cambridge, MD

Cozy River House in the Historic District of Cambridge, MD is a holiday home in Dorchester County, 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 $2,195.

From$314/night
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New, Intown Waterfront Townhome wPool & Location! - Dorchester County, MD

New, Intown Waterfront Townhome wPool & Location!

Holiday Home, Dorchester County

New, Intown Waterfront Townhome wPool & Location! is a holiday home in Dorchester County, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About New, Intown Waterfront Townhome wPool & Location!

New, Intown Waterfront Townhome wPool & Location! is a holiday home in Dorchester County, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,613.

From$373/night
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Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina - Dorchester County, MD

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Holiday Home, Dorchester County

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina is a holiday home in Dorchester County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina is a holiday home in Dorchester County, 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 $3,058.

From$437/night
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Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21 - Dorchester County, MD

Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21

Holiday Home, Dorchester County

Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21 is a holiday home in Dorchester County, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21

Relaxing getaway at Outrigger w/ plenty of space sleeping up to 21 is a holiday home in Dorchester County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,626.

From$947/night
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Vacation rentals with a kitchen in Dorchester County, MD

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

Waterfront Retreat < 4 Mi to Dtwn Cambridge! - Dorchester County, MD

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Holiday Home, Dorchester County

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a holiday home in Dorchester County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a holiday home in Dorchester County, 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 $3,970.

From$567/night
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Waterfront Retreat < 4 Mi to Dtwn Cambridge! - Dorchester County, MD

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Cottage, Dorchester County

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a cottage in Dorchester County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a cottage in Dorchester County, 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 $4,827.

From$578/night
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New Island Home on the Chesapeake Bay Sunsets - Dorchester County, MD

New Island Home on the Chesapeake Bay Sunsets

Holiday Home, Dorchester County

New Island Home on the Chesapeake Bay Sunsets is a holiday home in Dorchester County, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About New Island Home on the Chesapeake Bay Sunsets

New Island Home on the Chesapeake Bay Sunsets is a holiday home in Dorchester County, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,352.

From$622/night
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Waterfront Nature/Outdoor Lovers Secluded Estate - Dorchester County, MD

Waterfront Nature/Outdoor Lovers Secluded Estate

Holiday Home, Dorchester County

Waterfront Nature/Outdoor Lovers Secluded Estate is a holiday home in Dorchester County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Waterfront Nature/Outdoor Lovers Secluded Estate

Waterfront Nature/Outdoor Lovers Secluded Estate is a holiday home in Dorchester County, 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 $4,626.

From$661/night
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Family-friendly vacation rentals in Dorchester County, MD

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

Cottage on the Bay - Dorchester County, MD

Cottage on the Bay

Holiday Home, Dorchester County

Cottage on the Bay is a holiday home in Dorchester County, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cottage on the Bay

Cottage on the Bay is a holiday home in Dorchester County, 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 $2,109.

From$301/night
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The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula - Dorchester County, MD

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

Cottage, Dorchester County

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula is a cottage in Dorchester County, with easy beach access, parking, and kitchen access. This stay gives…

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About The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula

The Cottage at Heron Cove is a Cozy waterfront cottage on a Secluded Peninsula is a cottage in Dorchester County, 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 $2,136.

From$305/night
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The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge - Dorchester County, MD

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Condo, Dorchester County

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge is a condo in Dorchester County, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge is a condo in Dorchester County, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,695.

From$385/night
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Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres - Dorchester County, MD

Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

Holiday Home, Dorchester County

Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres is a holiday home in Dorchester County, with easy beach access and kitchen access. This stay gives travelers…

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About Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres

Fabulous Beach House on Elliott Island -beautiful sandy beach, tranquil 6 acres is a holiday home in Dorchester County, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,080.

From$440/night
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