Vacation rentals in Chestertown, MD

21 available vacation rental offers

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Best vacation rentals and Airbnb offers in Chestertown, MD

Life is better at the RIVER!--Cozy waterfront cottage - Chestertown, MD
10 ★ 114 reviews

Life is better at the RIVER!--Cozy waterfront cottage

Cottage, Chestertown

Life is better at the RIVER!--Cozy waterfront cottage is a cottage in Chestertown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Life is better at the RIVER!--Cozy waterfront cottage

Life is better at the RIVER!--Cozy waterfront cottage is a cottage in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,462.

From$209/night
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Eastern Shore Get Away - Chestertown, MD
10 ★ 89 reviews

Eastern Shore Get Away

Apartment, Chestertown

Eastern Shore Get Away is a apartment in Chestertown, 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 Eastern Shore Get Away

Eastern Shore Get Away is a apartment in Chestertown, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,129.

From$161/night
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Eagles Point Landing-Private Pool, Dock, Pickleball - Chestertown, MD
10 ★ 61 reviews

Eagles Point Landing-Private Pool, Dock, Pickleball

Holiday Home, Chestertown

Eagles Point Landing-Private Pool, Dock, Pickleball is a holiday home in Chestertown, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Eagles Point Landing-Private Pool, Dock, Pickleball

Eagles Point Landing-Private Pool, Dock, Pickleball is a holiday home in Chestertown, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $10,128.

From$1,447/night
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BEACH WITHOUT THE BUSTLE - Chestertown, MD
10 ★ 40 reviews

BEACH WITHOUT THE BUSTLE

Condo, Chestertown

BEACH WITHOUT THE BUSTLE is a condo in Chestertown, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About BEACH WITHOUT THE BUSTLE

BEACH WITHOUT THE BUSTLE is a condo in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,742.

From$249/night
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Family-friendly vacation rentals in Chestertown, MD

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

Waterfront Estate w Private Pier, Game Room & Bar - Chestertown, MD
9.6 ★ 40 reviews

Waterfront Estate w Private Pier, Game Room & Bar

Holiday Home, Chestertown

Waterfront Estate w Private Pier, Game Room & Bar is a holiday home in Chestertown, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Waterfront Estate w Private Pier, Game Room & Bar

Waterfront Estate w Private Pier, Game Room & Bar is a holiday home in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $9,868.

From$1,410/night
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Church Creek Cottage - Chestertown, MD

Church Creek Cottage

Cottage, Chestertown

Church Creek Cottage is a cottage in Chestertown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Church Creek Cottage

Church Creek Cottage is a cottage in Chestertown, 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, free wifi, kitchen, with kitchen, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,567.

From$367/night
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family friendly nice quiet neighborhood close to most major cities - Chestertown, MD

family friendly nice quiet neighborhood close to most major cities

Holiday Home, Chestertown

family friendly nice quiet neighborhood close to most major cities is a holiday home in Chestertown, 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 Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,251.

From$607/night
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Pet-friendly vacation rentals in Chestertown, MD

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

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully - Chestertown, MD
10 ★ 15 reviews

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Holiday Home, Chestertown

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully is a holiday home in Chestertown, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully is a holiday home in Chestertown, 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, hot tub, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $9,984.

From$1,426/night
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Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets - Chestertown, MD
10 ★ 9 reviews

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Holiday Home, Chestertown

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets is a holiday home in Chestertown, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets is a holiday home in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,536.

From$791/night
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Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach | - Chestertown, MD
10 ★ 8 reviews

Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |

Holiday Home, Chestertown

Centreville Waterfront Farm · 170 Acres · Pool · Private Dock · Private Beach · is a holiday home in Chestertown, with pet-friendly space, pool access, and easy beach access. This stay…

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About Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |

Centreville Waterfront Farm · 170 Acres · Pool · Private Dock · Private Beach · is a holiday home in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,370.

From$767/night
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Grays Inn Creek Waterfront Pvt Dock Kayaks & View - Chestertown, MD
10 ★ 6 reviews

Grays Inn Creek Waterfront Pvt Dock Kayaks & View

Holiday Home, Chestertown

Grays Inn Creek Waterfront Pvt Dock Kayaks & View is a holiday home in Chestertown, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Grays Inn Creek Waterfront Pvt Dock Kayaks & View

Grays Inn Creek Waterfront Pvt Dock Kayaks & View is a holiday home in Chestertown, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,573.

From$1,082/night
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Other places to stay in Chestertown, MD

motelsChestertown motels