Vacation rentals in Hillsboro, MD

113 available vacation rental offers

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Best vacation rentals and Airbnb offers in Hillsboro, MD

3 Mi to Washington College! Updated Home w/ Patio - Hillsboro, MD

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Hillsboro

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Hillsboro, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Hillsboro, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,421.

From$135/night
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Woodsy + Secluded! Amish Country Retreat in Hartly - Hillsboro, MD

Woodsy + Secluded! Amish Country Retreat in Hartly

Cottage, Hillsboro

Woodsy + Secluded! Amish Country Retreat in Hartly is a cottage in Hillsboro, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Woodsy + Secluded! Amish Country Retreat in Hartly

Woodsy + Secluded! Amish Country Retreat in Hartly is a cottage in Hillsboro, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,334.

From$160/night
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Adorable 2-bedroom bungalow near Easton, Denton - Hillsboro, MD

Adorable 2-bedroom bungalow near Easton, Denton

Holiday Home, Hillsboro

Adorable 2-bedroom bungalow near Easton, Denton is a holiday home in Hillsboro, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Adorable 2-bedroom bungalow near Easton, Denton

Adorable 2-bedroom bungalow near Easton, Denton is a holiday home in Hillsboro, with parking 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, parking, paid parking, and fireplace.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,452.

From$165/night
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3 Mi to Washington College! Updated Home w/ Patio - Hillsboro, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Hillsboro

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Hillsboro, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Hillsboro, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,212.

From$173/night
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Family-friendly vacation rentals in Hillsboro, MD

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

Charming cottage with Pool Access and WiFi in lovely Rock Hall - Hillsboro, MD

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Cottage, Hillsboro

Charming cottage with Pool Access and WiFi in lovely Rock Hall is a cottage in Hillsboro, with pool access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall is a cottage in Hillsboro, with 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: free cancellation, pool, free wifi, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,595.

From$228/night
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Peaceful getaway convenient to local amenities including beach, boating & food - Hillsboro, MD

Peaceful getaway convenient to local amenities including beach, boating & food

Cottage, Hillsboro

Peaceful getaway convenient to local amenities including beach, boating & food is a cottage in Hillsboro, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Peaceful getaway convenient to local amenities including beach, boating & food

Peaceful getaway convenient to local amenities including beach, boating & food is a cottage in Hillsboro, 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 $1,615.

From$231/night
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Perfect Waterview Cottage - St. Michaels Getaway - Hillsboro, MD

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Hillsboro

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Hillsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Perfect Waterview Cottage - St. Michaels Getaway

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,876.

From$268/night
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Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - Hillsboro, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Cottage, Hillsboro

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a cottage in Hillsboro, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a cottage in Hillsboro, 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 $2,738.

From$308/night
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Pet-friendly vacation rentals in Hillsboro, MD

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

3BR Dog-friendly Townouse w/ Grill, Fireplace, AC - Hillsboro, MD

3BR Dog-friendly Townouse w/ Grill, Fireplace, AC

Apartment, Hillsboro

3BR Dog-friendly Townouse w/ Grill, Fireplace, AC is a apartment in Hillsboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About 3BR Dog-friendly Townouse w/ Grill, Fireplace, AC

3BR Dog-friendly Townouse w/ Grill, Fireplace, AC is a apartment in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,790.

From$213/night
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8 Mi to Dover Motor Speedway! Dog-Friendly Retreat - Hillsboro, MD

8 Mi to Dover Motor Speedway! Dog-Friendly Retreat

Holiday Home, Hillsboro

8 Mi to Dover Motor Speedway! Dog-Friendly Retreat is a holiday home in Hillsboro, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About 8 Mi to Dover Motor Speedway! Dog-Friendly Retreat

8 Mi to Dover Motor Speedway! Dog-Friendly Retreat is a holiday home in Hillsboro, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,758.

From$251/night
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Cozy home in Milford/Harrington for relaxing stays! - Hillsboro, MD

Cozy home in Milford/Harrington for relaxing stays!

Holiday Home, Hillsboro

Cozy home in Milford/Harrington for relaxing stays! is a holiday home in Hillsboro, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Cozy home in Milford/Harrington for relaxing stays!

Cozy home in Milford/Harrington for relaxing stays! is a holiday home in Hillsboro, with pet-friendly space 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, pet friendly, pets friendly, and washer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,892.

From$270/night
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Eastons Urban Oasis- centrally located townhome in Talbot County - Hillsboro, MD

Eastons Urban Oasis- centrally located townhome in Talbot County

Holiday Home, Hillsboro

Eastons Urban Oasis- centrally located townhome in Talbot County is a holiday home in Hillsboro, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Eastons Urban Oasis- centrally located townhome in Talbot County

Eastons Urban Oasis- centrally located townhome in Talbot County is a holiday home in Hillsboro, 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, parking, free parking, fireplace, and washer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,441.

From$349/night
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Vacation rentals with a pool in Hillsboro, MD

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

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! - Hillsboro, MD

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Holiday Home, Hillsboro

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a holiday home in Hillsboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo! is a holiday home in Hillsboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,446.

From$349/night
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Inn at Haven Harbour - Hillsboro, MD

Inn at Haven Harbour

B & B, Hillsboro

Inn at Haven Harbour is a b & b in Hillsboro, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Haven Harbour

Inn at Haven Harbour is a b & b in Hillsboro, 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 breakfast, pool, free wifi, beachfront, and beach front.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,103.

From$251/night
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Inn at Huntingfield Creek - Hillsboro, MD

Inn at Huntingfield Creek

B & B, Hillsboro

Inn at Huntingfield Creek is a b & b in Hillsboro, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Hillsboro, 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 breakfast, pool, free wifi, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,490.

From$320/night
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Inn at Huntingfield Creek - Hillsboro, MD

Inn at Huntingfield Creek

B & B, Hillsboro

Inn at Huntingfield Creek is a b & b in Hillsboro, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Hillsboro, 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, free wifi, and for couples.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,497.

From$320/night
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Vacation rentals with a kitchen in Hillsboro, MD

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

Cute waterfront apartment -- 8 min from the beach! - Hillsboro, MD

Cute waterfront apartment -- 8 min from the beach!

Apartment, Hillsboro

Cute waterfront apartment -- 8 min from the beach! is a apartment in Hillsboro, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cute waterfront apartment -- 8 min from the beach!

Cute waterfront apartment -- 8 min from the beach! is a apartment in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,534.

From$219/night
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Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River - Hillsboro, MD

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Apartment, Hillsboro

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Hillsboro, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River is a apartment in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,861.

From$266/night
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Cottage #4 Chesapeake Blue down the drive way. - Hillsboro, MD

Cottage #4 Chesapeake Blue down the drive way.

Cottage, Hillsboro

Cottage #4 Chesapeake Blue down the drive way. is a cottage in Hillsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cottage #4 Chesapeake Blue down the drive way.

Cottage #4 Chesapeake Blue down the drive way. is a cottage in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,896.

From$271/night
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River Cottage, Chestertown - Hillsboro, MD

River Cottage, Chestertown

Holiday Home, Hillsboro

River Cottage, Chestertown is a holiday home in Hillsboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About River Cottage, Chestertown

River Cottage, Chestertown is a holiday home in Hillsboro, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,171.

From$310/night
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