Vacation rentals in Fairlee, MD

47 available vacation rental offers

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Best vacation rentals and Airbnb offers in Fairlee, MD

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

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Fairlee

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Fairlee, 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 Fairlee, 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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3 Mi to Washington College! Updated Home w/ Patio - Fairlee, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Fairlee

3 Mi to Washington College! Updated Home w/ Patio is a holiday home in Fairlee, 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 Fairlee, 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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Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! - Fairlee, MD

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment, Fairlee

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Fairlee, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! is a apartment in Fairlee, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,249.

From$178/night
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SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall - Fairlee, MD

SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall

Apartment, Fairlee

SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall is a apartment in Fairlee, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall

SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall is a apartment in Fairlee, with 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, parking, free parking, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,358.

From$194/night
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Family-friendly vacation rentals in Fairlee, MD

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

River Cottage, Chestertown - Fairlee, MD

River Cottage, Chestertown

Holiday Home, Fairlee

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

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About River Cottage, Chestertown

River Cottage, Chestertown is a holiday home in Fairlee, 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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Chesapeake Bay Getaway in Rock Hall - Fairlee, MD

Chesapeake Bay Getaway in Rock Hall

Holiday Home, Fairlee

Chesapeake Bay Getaway in Rock Hall is a holiday home in Fairlee, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chesapeake Bay Getaway in Rock Hall

Chesapeake Bay Getaway in Rock Hall is a holiday home in Fairlee, 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,181.

From$312/night
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Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD - Fairlee, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Holiday Home, Fairlee

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Fairlee, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Fairlee, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,184.

From$312/night
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Bayside Cottage steps from Rock Hall Harbor - Fairlee, MD

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Fairlee

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Fairlee, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Fairlee, 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 $2,330.

From$333/night
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Pet-friendly vacation rentals in Fairlee, MD

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

Beautiful Retreat Located in Rock Hall - walk to everything! - Fairlee, MD

Beautiful Retreat Located in Rock Hall - walk to everything!

Holiday Home, Fairlee

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Fairlee, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Beautiful Retreat Located in Rock Hall - walk to everything!

Beautiful Retreat Located in Rock Hall - walk to everything! is a holiday home in Fairlee, 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 $2,093.

From$299/night
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200 steps to the beach! - Fairlee, MD

200 steps to the beach!

Holiday Home, Fairlee

200 steps to the beach! is a holiday home in Fairlee, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 200 steps to the beach!

200 steps to the beach! is a holiday home in Fairlee, 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, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,236.

From$319/night
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Serene Waterfront Cottage with dock and gorgeous views. - Fairlee, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Fairlee

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Fairlee, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views. is a holiday home in Fairlee, 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, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,390.

From$341/night
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Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. - Fairlee, MD

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town.

Holiday Home, Fairlee

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. is a holiday home in Fairlee, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town.

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. is a holiday home in Fairlee, with pet-friendly space. 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,946.

From$421/night
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Vacation rentals with a pool in Fairlee, MD

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

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. - Fairlee, MD

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Holiday Home, Fairlee

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Fairlee, with pool access, easy beach access, and kitchen access. This stay gives…

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About A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Fairlee, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $8,223.

From$1,175/night
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Historic Manor House on Beautiful Eastern Shore Estate - Fairlee, MD

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Home, Fairlee

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Fairlee, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Historic Manor House on Beautiful Eastern Shore Estate

Historic Manor House on Beautiful Eastern Shore Estate is a holiday home in Fairlee, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $9,219.

From$1,317/night
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Inn at Huntingfield Creek - Fairlee, MD

Inn at Huntingfield Creek

B & B, Fairlee

Inn at Huntingfield Creek is a b & b in Fairlee, 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 Fairlee, 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 - Fairlee, MD

Inn at Huntingfield Creek

B & B, Fairlee

Inn at Huntingfield Creek is a b & b in Fairlee, 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 Fairlee, 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 parking in Fairlee, MD

Find vacation rentals that make arriving by car easier.

Beachcomber Suite - Fairlee, MD

Beachcomber Suite

Apartment, Fairlee

Beachcomber Suite is a apartment in Fairlee, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Beachcomber Suite

Beachcomber Suite is a apartment in Fairlee, 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 $1,331.

From$190/night
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Circa 1900 Home in the Heart of Historic Downtown Chestertown - Fairlee, MD

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Home, Fairlee

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Fairlee, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Circa 1900 Home in the Heart of Historic Downtown Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown is a holiday home in Fairlee, 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 $2,213.

From$316/night
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Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall - Fairlee, MD

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Holiday Home, Fairlee

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Fairlee, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall is a holiday home in Fairlee, 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, parking, free parking, washer, and dryer.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,234.

From$319/night
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Brampton 1860 - Fairlee, MD

Brampton 1860

B & B, Fairlee

Brampton 1860 is a b & b in Fairlee, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Brampton 1860

Brampton 1860 is a b & b in Fairlee, 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 breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,978.

From$383/night
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Vacation rentals with a kitchen in Fairlee, MD

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

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home - Fairlee, MD

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

Holiday Home, Fairlee

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Fairlee, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home is a holiday home in Fairlee, 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 $2,604.

From$372/night
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Newly renovated single family home with attached guest suite - Fairlee, MD

Newly renovated single family home with attached guest suite

Holiday Home, Fairlee

Newly renovated single family home with attached guest suite is a holiday home in Fairlee, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite is a holiday home in Fairlee, with 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 $2,675.

From$382/night
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Riverside at Pear Tree Point--Waterfront Escape - Fairlee, MD

Riverside at Pear Tree Point--Waterfront Escape

Holiday Home, Fairlee

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Fairlee, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Riverside at Pear Tree Point--Waterfront Escape

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Fairlee, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,809.

From$401/night
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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown - Fairlee, MD

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Holiday Home, Fairlee

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Fairlee, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown is a holiday home in Fairlee, 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 $3,084.

From$441/night
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