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Holiday homes in Chestertown

Enjoy your stay and find the best Holiday homes in Chestertown at affordable prices

Searching for a holiday home in Chestertown (Maryland)? Explore a great selection of vacation homes in Chestertown to find the one that best fits to your needs, starting from $136 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Chestertown and region (50 miles)
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office in Chestertown, USA

Walk to the Beach with Deck, Fireplace,...

Holiday home in Chestertown, Maryland , 8630 Elm Road
Comfortable Home with Deck, Fireplace, BBQ Grill and Boat Ramp Oh My is set in Chestertown and offers free bikes, a shared lounge and a restaurant.
  • Parking
  • Restaurant
  • Pets allowed
  • Bar
  • Family rooms

Superb 3 Reviews 9.0

from $234.00 Show details »

Beautiful Middle River Retreat with Boat Dock! in Middle River, USA

Beautiful Middle River Retreat with Boat...

Holiday home in Middle River near Chestertown, Maryland
Beautiful Middle River Retreat with Boat Dock! is situated in Middle River, 23 km from Clifton Park, 24 km from Fells Point, as well as 24 km from Har...
  • Parking

no reviews

from $236.00 Show details »

Remodeled Abingdon House with Spacious Yard! in Abingdon, USA

Remodeled Abingdon House with Spacious Y...

Holiday home in Abingdon near Chestertown, Maryland
Situated 37 km from Towson University, 37 km from Korean War Memorial and 37 km from Fells Point, Remodeled Abingdon House with Spacious Yard! feature...
  • Parking

no reviews

from $136.00 Show details »

Adorable 2-bedroom bungalow near Easton, Denton in Denton, USA

Adorable 2-bedroom bungalow near Easton,...

Holiday home in Denton near Chestertown, Maryland , 13508 Tuckahoe Avenue
Located in Denton in the Maryland region, Adorable 2-bedroom bungalow near Easton, Denton features a patio.
  • Parking
  • Family rooms

no reviews

from $190.67 Show details »

Relax in Nature & Serenity at Bird River Cottage! in Middle River, USA

Relax in Nature & Serenity at Bird River...

Holiday home in Middle River near Chestertown, Maryland , 10425 Bird River Road
Situated in Middle River, within 19 km of Korean War Memorial and 20 km of Clifton Park, Relax in Nature & Serenity at Bird River Cottage! offers acco...
  • Parking
  • Pets allowed
  • Family rooms
  • Kids' outdoor play equipment

no reviews

from $325.00 Show details »

Waterfront Annapolis Home Fire Pit and Fishing Pier in Annapolis, USA

Waterfront Annapolis Home Fire Pit and F...

Holiday home in Annapolis near Chestertown, Maryland
Waterfront Annapolis Home Fire Pit and Fishing Pier is located in Annapolis, 14 km from Annapolis Harbor, 42 km from Inner Harbor, and 46 km from Carr...
  • Parking
  • Pets allowed
  • Internet facilities
  • Shower
  • Bath

Superb 8 Reviews 9.3

from $315.00 Show details »

Annapolis Charm Waterfront Getaway - Near Beach - FISH & CRAB from your PRIVATE PIER! in Annapolis, USA

Annapolis Charm Waterfront Getaway - Nea...

Villa in Annapolis near Chestertown, Maryland , 1709 River Road
Boasting river views, Annapolis Charm Waterfront Chesapeake Bay Getaway Near Beach - Private Pier! features accommodation with a balcony and a kettle,...
  • Parking
  • Family rooms

Exceptional 5 Reviews 9.6

from $421.67 Show details »

Off The Beaten Path Rancher! Beautifully Made in Rosedale, USA

Off The Beaten Path Rancher! Beautifully...

Holiday home in Rosedale near Chestertown, Maryland , 200 Potomac Avenue
Off The Beaten Path Rancher!
  • Parking
  • Family rooms

no reviews

from $237.72 Show details »

Baltimore Home Base with Pool, Hot Tub and Grill! in Baltimore, USA

Baltimore Home Base with Pool, Hot Tub a...

Holiday home in Baltimore near Chestertown, Maryland
Set in Baltimore, 7 km from Korean War Memorial, 7.5 km from Fells Point and 8.7 km from Clifton Park, Baltimore Home Base with Pool, Hot Tub and Gril...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $213.67 Show details »

Idyllic Pasadena Retreat with Garden and Hot Tub! in Glen Burnie, USA

Idyllic Pasadena Retreat with Garden and...

Holiday home in Glen Burnie near Chestertown, Maryland
Featuring a hot tub, Idyllic Pasadena Retreat with Garden and Hot Tub! is located in Glen Burnie.
  • Parking
  • Pets allowed

no reviews

from $397.00 Show details »

Chic & Cozy City Living Enjoy Baltimore in Style in Baltimore, USA

Chic & Cozy City Living Enjoy Baltimore...

Holiday home in Baltimore near Chestertown, Maryland , 421 Drew Street
Chic & Cozy City Living Enjoy Baltimore in Style is set in Baltimore, 4.9 km from Fells Point, 5.5 km from Harbor East Marina, as well as 5.5 km from ...
  • Parking
  • Family rooms

no reviews

from $171.12 Show details »

Chase Creek Retreat in Annapolis, USA

Chase Creek Retreat

Holiday home in Annapolis near Chestertown, Maryland
Situated in Annapolis in the Maryland region, Chase Creek Retreat features a patio.
  • Parking
  • Pets allowed

no reviews

from $380.67 Show details »

Baltimore Townhome, Walk to Patterson Park! in Baltimore, USA

Baltimore Townhome, Walk to Patterson Pa...

Holiday home in Baltimore near Chestertown, Maryland
Baltimore Townhome, Walk to Patterson Park! is set in Baltimore, 3.3 km from Fells Point, 3.9 km from Harbor East Marina, as well as 4.9 km from Pier ...
  • Parking
  • Pets allowed

no reviews

from $152.00 Show details »

Cozy Bel Air Home - Walk to Main Street Shops in Bel Air, USA

Cozy Bel Air Home - Walk to Main Street...

Holiday home in Bel Air near Chestertown, Maryland
Cozy Bel Air Home - Walk to Main Street Shops is set in Bel Air, 43 km from Clifton Park, 44 km from Korean War Memorial, and 44 km from Fells Point.
  • Parking

no reviews

from $137.00 Show details »

The Pacific Fleet House in Annapolis, USA

The Pacific Fleet House

Holiday home in Annapolis near Chestertown, Maryland
Set in Annapolis, 1.8 km from Annapolis Harbor and 48 km from Carroll Park, The Pacific Fleet House offers accommodation with free WiFi, air condition...

no reviews

from $425.29 Show details »

Riverfront Port Deposit House with Deck and Yard! in Havre de Grace, USA

Riverfront Port Deposit House with Deck...

Holiday home in Havre de Grace near Chestertown, Maryland
Located in Havre de Grace, 39 km from Tennis Courts, 39 km from Tennis Court and 39 km from University of Delaware, Riverfront Port Deposit House with...
  • Parking

Superb 3 Reviews 9.3

from $371.00 Show details »

The Little House in Annapolis, USA

The Little House

Holiday home in Annapolis near Chestertown, Maryland
Set in Annapolis, 2.5 km from Annapolis Harbor and 47 km from Carroll Park, The Little House offers air-conditioned accommodation with a patio and fre...
  • Parking

Disappointing 1 Reviews 4.0

from $338.66 Show details »

Sunny Glen Burnie Home - On-Site Water Access in Glen Burnie, USA

Sunny Glen Burnie Home - On-Site Water A...

Holiday home in Glen Burnie near Chestertown, Maryland
Boasting a spa bath, Sunny Glen Burnie Home - On-Site Water Access is situated in Glen Burnie.
  • Parking

no reviews

from $371.33 Show details »

Cozy Lakeside Maryland Home - 12 Mi to Dtwn! in Glen Burnie, USA

Cozy Lakeside Maryland Home - 12 Mi to D...

Holiday home in Glen Burnie near Chestertown, Maryland
Cozy Lakeside Maryland Home - 12 Mi to Dtwn! is set in Glen Burnie, 16 km from Inner Harbor, 16 km from Baltimore Convention Center, as well as 17 km ...
  • Parking

no reviews

from $155.00 Show details »

Modern Urban Escape in the Heart of Baltimore! in Baltimore, USA

Modern Urban Escape in the Heart of Balt...

Holiday home in Baltimore near Chestertown, Maryland
Modern Urban Escape in the Heart of Baltimore! is located in the Canton district of Baltimore, 1.3 km from Fells Point, 1.9 km from Harbor East Marina...
  • Parking
  • Pets allowed

no reviews

from $147.33 Show details »

Charming Baltimore Home with Deck and Fire Pit! in Baltimore, USA

Charming Baltimore Home with Deck and Fi...

Holiday home in Baltimore near Chestertown, Maryland
Charming Baltimore Home with Deck and Fire Pit! is located in Baltimore, 6.7 km from Clifton Park, and provides a patio, garden, and free WiFi.
  • Parking
  • Pets allowed

no reviews

from $342.33 Show details »

Annapolis Vacation Home 2 Mi to Quiet Waters Park in Annapolis, USA

Annapolis Vacation Home 2 Mi to Quiet Wa...

Holiday home in Annapolis near Chestertown, Maryland
Situated 2.9 km from Carrs Beach, 5.2 km from Annapolis Harbor and 44 km from Addison Road-Seat Pleasant, Annapolis Vacation Home 2 Mi to Quiet Waters...
  • Parking

no reviews

from $371.00 Show details »

Family Harbor Hideaway, Your Chic City Retreat! in Baltimore, USA

Family Harbor Hideaway, Your Chic City R...

Holiday home in Baltimore near Chestertown, Maryland , Webster Street 1622
Situated in Baltimore, 1.3 km from Inner Harbor, 2.4 km from Historic Ships in Baltimore and 2.9 km from Baltimore Convention Center, Luxury Retreat N...
  • Parking

no reviews

from $213.00 Show details »

Baltimore Abode, Walk to Cross Street Market! in Baltimore, USA

Baltimore Abode, Walk to Cross Street Ma...

Holiday home in Baltimore near Chestertown, Maryland
Set in Baltimore, 1.6 km from Inner Harbor and 1.7 km from Baltimore Convention Center, Baltimore Abode, Walk to Cross Street Market! provides accommo...
  • Parking

no reviews

from $414.33 Show details »

Baltimore Abode, Walk to Cross Street Market! in Baltimore, USA

Baltimore Abode, Walk to Cross Street Ma...

Holiday home in Baltimore near Chestertown, Maryland
Set in Baltimore, 1.6 km from Inner Harbor and 1.7 km from Baltimore Convention Center, Baltimore Abode, Walk to Cross Street Market! provides accommo...
  • Parking

no reviews

from $414.33 Show details »

Midtown Baltimore Hub Half Mi to Penn Station in Baltimore, USA

Midtown Baltimore Hub Half Mi to Penn St...

Holiday home in Baltimore near Chestertown, Maryland
Located in the centre of Baltimore, 700 metres from Historic Ships in Baltimore and less than 1 km from The Walters Art Museum, Midtown Baltimore Hub ...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 10.0

from $264.00 Show details »

Number of Holiday homes in Chestertown 47
Number of guest ratings 374
Average price per night $326.74
Lowest price per night $136.00
Highest price per night $602.00

Most popular Holiday-homes in Chestertown

The most popular Holiday-homes in Chestertown based on average guest rating (Top 10).

Cheapest Holiday-homes in Chestertown

The cheapest Holiday-homes in Chestertown based on room rate per night (Top 10).

Most booked Holiday-homes in Chestertown

The most booked Holiday-homes in Chestertown based on popularity with guests (Top 10).

Holiday homes in Chestertown (Maryland), comfortable and familiar

Staying in a holiday or vacation home in Chestertown can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chestertown for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chestertown should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com