Vacation rentals in Woolford, MD

46 available vacation rental offers

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Best vacation rentals and Airbnb offers in Woolford, MD

Cambridge Apt in Walkable Neighborhood - Woolford, MD

Cambridge Apt in Walkable Neighborhood

Apartment, Woolford

Cambridge Apt in Walkable Neighborhood is a apartment in Woolford, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood is a apartment in Woolford, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,653.

From$187/night
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Station House East: Upscale Loft in the Historic District Cambridge, MD - Woolford, MD

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

Condo, Woolford

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

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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 Woolford, 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 - Woolford, MD

La Casa Azul . with Wi-Fi, AC

Holiday Home, Woolford

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

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About La Casa Azul . with Wi-Fi, AC

La Casa Azul . with Wi-Fi, AC is a holiday home in Woolford, 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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Cambridge Apt in Walkable Neighborhood - Woolford, MD

Cambridge Apt in Walkable Neighborhood

Apartment, Woolford

Cambridge Apt in Walkable Neighborhood is a apartment in Woolford, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood is a apartment in Woolford, 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 $1,496.

From$214/night
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Vacation rentals with a pool in Woolford, 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! - Woolford, MD

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Holiday Home, Woolford

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

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

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!

Apartment, Woolford

< 1 Mi to Dtwn: Waterfront Townhome in Cambridge! is a apartment in Woolford, with pool access, easy beach access, and kitchen access. 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 apartment in Woolford, 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 $3,744.

From$448/night
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Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD - Woolford, MD

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

Holiday Home, Woolford

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

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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 Woolford, 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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B&B - The Lawson - Woolford, MD

B&B - The Lawson

B & B, Woolford

B&B - The Lawson is a b & b in Woolford, with pool access. 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 B&B - The Lawson

B&B - The Lawson is a b & b in Woolford, 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: pool, free wifi, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,200.

From$314/night
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Vacation rentals with parking in Woolford, MD

Find vacation rentals that make arriving by car easier.

Waterfront Gem < 1 Mi to Dtwn Cambridge! - Woolford, MD

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Apartment, Woolford

Waterfront Gem < 1 Mi to Dtwn Cambridge! is a apartment in Woolford, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Waterfront Gem < 1 Mi to Dtwn Cambridge!

Waterfront Gem < 1 Mi to Dtwn Cambridge! is a apartment in Woolford, 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 $2,344.

From$335/night
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Waterfront Gem < 1 Mi to Dtwn Cambridge! - Woolford, MD

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Apartment, Woolford

Waterfront Gem < 1 Mi to Dtwn Cambridge! is a apartment in Woolford, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Waterfront Gem < 1 Mi to Dtwn Cambridge!

Waterfront Gem < 1 Mi to Dtwn Cambridge! is a apartment in Woolford, 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 $2,830.

From$338/night
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Walk to Parks & Marina! Waterfront Cambridge Condo - Woolford, MD

Walk to Parks & Marina! Waterfront Cambridge Condo

Condo, Woolford

Walk to Parks & Marina! Waterfront Cambridge Condo is a condo in Woolford, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Walk to Parks & Marina! Waterfront Cambridge Condo

Walk to Parks & Marina! Waterfront Cambridge Condo is a condo in Woolford, 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 $2,752.

From$393/night
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Walk to Parks & Marina! Waterfront Cambridge Condo - Woolford, MD

Walk to Parks & Marina! Waterfront Cambridge Condo

Apartment, Woolford

Walk to Parks & Marina! Waterfront Cambridge Condo is a apartment in Woolford, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Walk to Parks & Marina! Waterfront Cambridge Condo

Walk to Parks & Marina! Waterfront Cambridge Condo is a apartment in Woolford, 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 $3,333.

From$401/night
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Pet-friendly vacation rentals in Woolford, MD

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

New, Intown Waterfront Townhome wPool & Location! - Woolford, MD

New, Intown Waterfront Townhome wPool & Location!

Holiday Home, Woolford

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

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About New, Intown Waterfront Townhome wPool & Location!

New, Intown Waterfront Townhome wPool & Location! is a holiday home in Woolford, 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 - Woolford, MD

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Holiday Home, Woolford

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina is a holiday home in Woolford, 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 Woolford, 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 - Woolford, MD

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

Holiday Home, Woolford

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

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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 Woolford, 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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Private 2 Acre Waterfront Family Retreat with Pool & Pier - Woolford, MD

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Holiday Home, Woolford

Private 2 Acre Waterfront Family Retreat with Pool & Pier is a holiday home in Woolford, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier is a holiday home in Woolford, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,548.

From$1,221/night
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Vacation rentals with a kitchen in Woolford, MD

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

Attractive Waterfront Home over looking Choptank River. Sleeps 5 - Woolford, MD

Attractive Waterfront Home over looking Choptank River. Sleeps 5

Holiday Home, Woolford

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

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

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Holiday Home, Woolford

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

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About Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a holiday home in Woolford, 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 $4,078.

From$583/night
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Waterfront Retreat < 4 Mi to Dtwn Cambridge! - Woolford, MD

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Cottage, Woolford

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

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About Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge! is a cottage in Woolford, 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 $4,962.

From$595/night
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Waterfront Nature/Outdoor Lovers Secluded Estate - Woolford, MD

Waterfront Nature/Outdoor Lovers Secluded Estate

Holiday Home, Woolford

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

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About Waterfront Nature/Outdoor Lovers Secluded Estate

Waterfront Nature/Outdoor Lovers Secluded Estate is a holiday home in Woolford, 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 Woolford, MD

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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) - Woolford, MD

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage, Woolford

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) is a cottage in Woolford, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

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About Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) is a cottage in Woolford, 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 $2,465.

From$352/night
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The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge - Woolford, MD

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Condo, Woolford

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

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

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

Condo, Woolford

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland is a condo in Woolford, 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 Woolford, 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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Private 9 acre Family Retreat on the Chesapeake Bay - Woolford, MD

Private 9 acre Family Retreat on the Chesapeake Bay

Holiday Home, Woolford

Private 9 acre Family Retreat on the Chesapeake Bay is a holiday home in Woolford, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Private 9 acre Family Retreat on the Chesapeake Bay

Private 9 acre Family Retreat on the Chesapeake Bay is a holiday home in Woolford, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,822.

From$689/night
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