Vacation rentals in Chester River, MD

48 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Chester River, MD

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

3 Mi to Washington College! Updated Home w/ Patio

Cottage, Chester River

3 Mi to Washington College! Updated Home w/ Patio is a cottage in Chester River, 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 cottage in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,423.

From$135/night
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3 Mi to Washington College! Updated Home w/ Patio - Chester River, MD

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$173/night
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Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! - Chester River, MD

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

Apartment, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,233.

From$176/night
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SWAN CREEK RETREAT This is a amazing garage apartment in Rock Hall - Chester River, MD

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

Apartment, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,358.

From$194/night
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Browse Vacation Rentals with a Pool in Chester River, 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. - Chester River, MD

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

Holiday Home, Chester River

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. is a holiday home in Chester River, 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 Chester River, 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 $8,223.

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

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Home, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,219.

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

Inn at Huntingfield Creek

B & B, Chester River

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

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

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

Inn at Huntingfield Creek

B & B, Chester River

Inn at Huntingfield Creek is a b & b in Chester River, 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 Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,497.

From$320/night
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Best Chester River, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

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

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

Apartment, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,861.

From$266/night
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Newly restored apartment in the heart of Chestertown - Chester River, MD

Newly restored apartment in the heart of Chestertown

Apartment, Chester River

Newly restored apartment in the heart of Chestertown is a apartment in Chester River, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown is a apartment in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,026.

From$289/night
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Circa 1900 Home in the Heart of Historic Downtown Chestertown - Chester River, MD

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Home, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 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 - Chester River, MD

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

Holiday Home, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$321/night
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Best Pet-Friendly Vacation Rentals in Chester River, MD

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

200 steps to the beach! - Chester River, MD

200 steps to the beach!

Holiday Home, Chester River

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

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About 200 steps to the beach!

200 steps to the beach! is a holiday home in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,236.

From$319/night
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Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. - Chester River, MD

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

Holiday Home, Chester River

Charming 3 bed/2 bath house in Rock Hall with a 3-min walk to restaurants/town. is a holiday home in Chester River, 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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,946.

From$421/night
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Waterfront! Private Dock, Boat Tie-Up & Near Town - Chester River, MD

Waterfront! Private Dock, Boat Tie-Up & Near Town

Holiday Home, Chester River

Waterfront! Private Dock, Boat Tie-Up & Near Town is a holiday home in Chester River, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront! Private Dock, Boat Tie-Up & Near Town is a holiday home in Chester River, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,499.

From$500/night
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family friendly nice quiet neighborhood close to most major cities - Chester River, MD

family friendly nice quiet neighborhood close to most major cities

Holiday Home, Chester River

family friendly nice quiet neighborhood close to most major cities is a holiday home in Chester River, with pet-friendly space, room for a group, and a quieter setting. This stay gives…

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About family friendly nice quiet neighborhood close to most major cities

family friendly nice quiet neighborhood close to most major cities is a holiday home in Chester River, with pet-friendly space, 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, pet friendly, pets friendly, washer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,323.

From$618/night
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Best Chester River, MD vacation rentals with a kitchen

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

Family Retreat at Lansdowne Manor - Chester River, MD

Family Retreat at Lansdowne Manor

Country House, Chester River

Family Retreat at Lansdowne Manor is a country house in Chester River, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor is a country house in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,484.

From$355/night
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Riverside at Pear Tree Point--Waterfront Escape - Chester River, MD

Riverside at Pear Tree Point--Waterfront Escape

Holiday Home, Chester River

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

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About Riverside at Pear Tree Point--Waterfront Escape

Riverside at Pear Tree Point--Waterfront Escape is a holiday home in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,809.

From$401/night
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Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! - Chester River, MD

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Holiday Home, Chester River

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Chester River, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore!

Bay Beach Oasis - Only 2 hours from DC, Philadelphia, or Baltimore! is a holiday home in Chester River, 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 $2,998.

From$428/night
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Private Waterfront Cottage On Langford Creek With Hot Tub & Pier - Chester River, MD

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

Holiday Home, Chester River

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier is a holiday home in Chester River, with easy beach access and kitchen access. This stay gives travelers a comfortable base…

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About Private Waterfront Cottage On Langford Creek With Hot Tub & Pier

Private Waterfront Cottage On Langford Creek With Hot Tub & Pier is a holiday home in Chester River, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,466.

From$495/night
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Our Favorite Family-Friendly Vacation Rentals in Chester River, MD

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

Chesapeake Bay Getaway in Rock Hall - Chester River, MD

Chesapeake Bay Getaway in Rock Hall

Holiday Home, Chester River

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

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About Chesapeake Bay Getaway in Rock Hall

Chesapeake Bay Getaway in Rock Hall is a holiday home in Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,181.

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

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

Holiday Home, Chester River

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD is a holiday home in Chester River, 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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,184.

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

Bayside Cottage steps from Rock Hall Harbor

Holiday Home, Chester River

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

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About Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor is a holiday home in Chester River, 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 $2,323.

From$332/night
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Serene Waterfront Cottage with dock and gorgeous views. - Chester River, MD

Serene Waterfront Cottage with dock and gorgeous views.

Holiday Home, Chester River

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

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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 Chester River, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,390.

From$341/night
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