Vacation Rentals Chestertown, MD
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Showing 53 Vacation Rentals from Chestertown, MD
Chestertown, MD Vacation Rentals:
Nightly rate
100 USD to 250 USD
Property type
Bed & Breakfast
Bedrooms
6
Sleeps
-
Bathrooms
4
Amenities:
Air Conditioning, Cable/Satellite TV, Computer Access, DVD Player, Fireplace, Hair Dryer, Hot Tub, Iron, Ironing Board, Non-Smoking, Phone, Refrigerator, Restaurant, TV, VCR, Wireless Internet Access
Air Conditioning, Cable/Satellite TV, Computer Access, DVD Player, Fireplace, Hair Dryer, Hot Tub, Iron, Ironing Board, Non-Smoking, Phone, Refrigerator, Restaurant, TV, VCR, Wireless Internet Access
Activities:
Beach, Canoeing, Fishing, Golf, Hiking, Kayaking, Museums, Shopping, Tennis, Watersports
Beach, Canoeing, Fishing, Golf, Hiking, Kayaking, Museums, Shopping, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:This property has been featured in Washingtonian, New York Magazine, Glamour, Philadelphia Inquirer, Baltimore Sun, Kent County News, Ten Best Inns in the Country, New York Times, Washington Post, National Geographic Traveler. ;
description:This property has been featured in Washingtonian, New York Magazine, Glamour, Philadelphia Inquirer, Baltimore Sun, Kent County News, Ten Best Inns in the Country, New York Times, Washington Post, National Geographic Traveler. ;
Nightly rate
165 USD to 310 USD
Property type
Bed & Breakfast
Bedrooms
12
Sleeps
-
Bathrooms
5
Amenities:
Air Conditioning, CD Player, Ceiling fans, Computer Access, DVD Player, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Lounge, Non-Smoking, Phone, Restaurant, Stereo, Swimming Pool, TV, VCR, Wireless Internet Access
Air Conditioning, CD Player, Ceiling fans, Computer Access, DVD Player, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Lounge, Non-Smoking, Phone, Restaurant, Stereo, Swimming Pool, TV, VCR, Wireless Internet Access
Activities:
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Massage, Museums, Restaurants, Shopping, Swimming, Tennis, Watersports
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Massage, Museums, Restaurants, Shopping, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:This property has been featured in Southern Living, Philadelphia, Diversions, Road Best Traveled, Washingtonian, Country Inns, New Choices, Chesapeake Life, Time Magazine., Today Show with Peter Greenberg, July 2005. ;
description:This property has been featured in Southern Living, Philadelphia, Diversions, Road Best Traveled, Washingtonian, Country Inns, New Choices, Chesapeake Life, Time Magazine., Today Show with Peter Greenberg, July 2005. ;
Nightly rate
199 USD to 439 USD
Property type
Bed & Breakfast
Bedrooms
8
Sleeps
-
Bathrooms
12
Amenities:
Air Conditioning, CD Player, DVD Player, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Non-Smoking, Pets OK, Phone, Room Service, Wireless Internet Access
Air Conditioning, CD Player, DVD Player, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Non-Smoking, Pets OK, Phone, Room Service, Wireless Internet Access
Activities:
Beach, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Museums, Shopping, Tennis
Beach, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Museums, Shopping, Tennis
Vacation Bed & Breakfast Description:
description:This property has been featured in New York Times, New York Daily News, Philadelphia Inquirer, Washington Post, Baltimore Sun, Los Angeles Times, Washingtonian, Southern Living, Philadelphia Magazine, Chesapeake Life. ;
description:This property has been featured in New York Times, New York Daily News, Philadelphia Inquirer, Washington Post, Baltimore Sun, Los Angeles Times, Washingtonian, Southern Living, Philadelphia Magazine, Chesapeake Life. ;
Nightly rate
140 USD to 240 USD
Property type
Bed & Breakfast
Bedrooms
2
Sleeps
-
Bathrooms
2
Amenities:
Air Conditioning, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Non-Smoking, Phone, Refrigerator, TV, Wireless Internet Access
Air Conditioning, Fireplace, Hair Dryer, Hot Tub, Internet Access, Iron, Ironing Board, Non-Smoking, Phone, Refrigerator, TV, Wireless Internet Access
Activities:
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Museums, Shopping, Tennis, Watersports, Yoga
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Museums, Shopping, Tennis, Watersports, Yoga
Vacation Bed & Breakfast Description:
description:This property has 6 total guest accommodations with private bath, 2 total suites, including 1 two-bedroom suite and 2 conference rooms. The types of beds available include King, Queen, Twin and Double. ;
description:This property has 6 total guest accommodations with private bath, 2 total suites, including 1 two-bedroom suite and 2 conference rooms. The types of beds available include King, Queen, Twin and Double. ;
Nightly rate
195 USD to 435 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Alarm Clock, Fireplace, Hot Tub, Internet Access, Ironing Board, Jacuzzi, Non-Smoking, Pets OK, Phone, Refrigerator, TV, VCR, Wireless Internet Access
Air Conditioning, Alarm Clock, Fireplace, Hot Tub, Internet Access, Ironing Board, Jacuzzi, Non-Smoking, Pets OK, Phone, Refrigerator, TV, VCR, Wireless Internet Access
Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:You can swing on the comfy porch swings and enjoy a cool breeze while sipping ice tea or lemonade. From this quiet spot observe the flight and hear the songs of Brampton's numerous birds. Swallows, gold finches, cardinals, hummingbirds, herons, egrets, Canada geese, wood ducks, woodpeckers, owls, blue birds, Baltimore orioles, and many other birds have been spotted on this property. ;
description:You can swing on the comfy porch swings and enjoy a cool breeze while sipping ice tea or lemonade. From this quiet spot observe the flight and hear the songs of Brampton's numerous birds. Swallows, gold finches, cardinals, hummingbirds, herons, egrets, Canada geese, wood ducks, woodpeckers, owls, blue birds, Baltimore orioles, and many other birds have been spotted on this property. ;
Nightly rate
165 USD to 310 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR, Wireless Internet Access
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR, Wireless Internet Access
Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that get-a-way from it all feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and... ;
description:Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that get-a-way from it all feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and... ;
Nightly rate
100 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Laundry, Microwave, Phone, Refrigerator, Stove, TV, Toaster, Wireless Internet Access
Air Conditioning, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Laundry, Microwave, Phone, Refrigerator, Stove, TV, Toaster, Wireless Internet Access
Activities:
Boating, Fishing, Hunting, Kayaking
Boating, Fishing, Hunting, Kayaking
Vacation Bed & Breakfast Description:
-
-
Nightly rate
165 USD to 310 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR, Wireless Internet Access
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR, Wireless Internet Access
Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that get-a-way from it all feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and... ;
description:Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that get-a-way from it all feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, on Maryland's Eastern Shore. Great Oak Manor speaks an elegant lifestyle gone by. It is conveniently accessible from Washington D.C., Baltimore and... ;
Nightly rate
155 USD to 285 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR
Air Conditioning, Alarm Clock, Balcony, DVD Player, Fireplace, Ironing Board, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Swimming Pool, TV, VCR
Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Snow Skiing, Swimming, Tennis, Watersports
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Historical Sites, Horseback Riding, Hunting, Kayaking, Massage, Restaurants, Sailing, Shopping, Sightseeing, Snow Skiing, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
description:Ten guest rooms located on the Chesapeake Bay, individually heated & air conditioned for your comfort, five with working fireplaces, seven with water views ;
description:Ten guest rooms located on the Chesapeake Bay, individually heated & air conditioned for your comfort, five with working fireplaces, seven with water views ;
Nightly rate
95 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
2
Amenities:
Air Conditioning, TV, VCR
Air Conditioning, TV, VCR
Activities:
Biking, Boating, Canoeing, Fishing, Golf, Hiking, Hunting, Kayaking, Sailing, Shopping, Watersports
Biking, Boating, Canoeing, Fishing, Golf, Hiking, Hunting, Kayaking, Sailing, Shopping, Watersports
Vacation Bed & Breakfast Description:
-
-
Nightly rate
165 USD to 310 USD
Property type
Bed & Breakfast
Bedrooms
11
Sleeps
-
Bathrooms
-
Amenities:
Phone, Swimming Pool
Phone, Swimming Pool
Activities:
Beach, Swimming
Beach, Swimming
Vacation Bed & Breakfast Description:
-
-
Nightly rate
250 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Internet Access, Ironing Board, Linens, Phone, Restaurant, TV, Wireless Internet Access
Internet Access, Ironing Board, Linens, Phone, Restaurant, TV, Wireless Internet Access
Activities:
-
-
Vacation Bed & Breakfast Description:
-
-
Nightly rate
Property type
Vacation Home
Bedrooms
5
Sleeps
15
Bathrooms
3.5
Amenities:
Air Conditioning, Cable/Satellite TV, DVD Player, Dishwasher, Full kitchen, Hot Tub, Laundry, Linens, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Utensils, Wireless Internet Access
Air Conditioning, Cable/Satellite TV, DVD Player, Dishwasher, Full kitchen, Hot Tub, Laundry, Linens, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, Utensils, Wireless Internet Access
Activities:
Basketball, Biking, Boating, Fishing, Golf, Hiking, Horseback Riding, Hunting, Jetskiing, Kayaking, Museums, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Water Skiing, Wildlife viewing
Basketball, Biking, Boating, Fishing, Golf, Hiking, Horseback Riding, Hunting, Jetskiing, Kayaking, Museums, Restaurants, Sailing, Shopping, Sightseeing, Swimming, Water Skiing, Wildlife viewing
Vacation Home Description:
description:KEY FEATURES Near Golf Child Friendly Near Shopping Near Restaurants Air Conditioning Fully Equipped Kitchen LOCATION TYPE Golf Fishing AMENITIES Child Friendly Air Conditioning Cable TV DVD Player Wireless Internet Access Washer/Dryer Spa Bath/Jetted Tub King Bed 4 Queen bed 2 Double Bed Twin Bed Telephone Parking Available Linens Included No Smoking No Pets Allowed Kitchen Level Within Rental 1 Fully Equipped Kitchen Microwave Dishwasher Utensils Refrigerator ATTRACTIONS Near Golf Near Shopping Near Restaurants Boating Fishing Sailing Jet Skiing Water Skiing Kayaking Swimming Hiking Wildlife Viewing Hunting Biking Horseback riding Museums Sightseeing Basketball Movie Theatre Contact by Email Contact by Phone Submit the form below to send your inquiry directly to the property owner .;
description:KEY FEATURES Near Golf Child Friendly Near Shopping Near Restaurants Air Conditioning Fully Equipped Kitchen LOCATION TYPE Golf Fishing AMENITIES Child Friendly Air Conditioning Cable TV DVD Player Wireless Internet Access Washer/Dryer Spa Bath/Jetted Tub King Bed 4 Queen bed 2 Double Bed Twin Bed Telephone Parking Available Linens Included No Smoking No Pets Allowed Kitchen Level Within Rental 1 Fully Equipped Kitchen Microwave Dishwasher Utensils Refrigerator ATTRACTIONS Near Golf Near Shopping Near Restaurants Boating Fishing Sailing Jet Skiing Water Skiing Kayaking Swimming Hiking Wildlife Viewing Hunting Biking Horseback riding Museums Sightseeing Basketball Movie Theatre Contact by Email Contact by Phone Submit the form below to send your inquiry directly to the property owner .;
Nightly rate
235 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Fireplace, Non-Smoking, Patio, Phone, Refrigerator, Swimming Pool, TV, VCR
Air Conditioning, Fireplace, Non-Smoking, Patio, Phone, Refrigerator, Swimming Pool, TV, VCR
Activities:
Badminton, Beach, Biking, Fishing, Golf, Hunting, Shopping, Snow Skiing, Swimming, Tennis, Watersports
Badminton, Beach, Biking, Fishing, Golf, Hunting, Shopping, Snow Skiing, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
-
-
Nightly rate
295 USD
Property type
Bed & Breakfast
Bedrooms
-
Sleeps
-
Bathrooms
-
Amenities:
Air Conditioning, Fireplace, Hot Tub, Non-Smoking, Patio, Refrigerator, Room Service, TV, VCR
Air Conditioning, Fireplace, Hot Tub, Non-Smoking, Patio, Refrigerator, Room Service, TV, VCR
Activities:
Biking, Boating, Canoeing, Fishing, Golf, Horseback Riding, Hunting, Kayaking, Sailing, Shopping, Swimming, Tennis, Watersports
Biking, Boating, Canoeing, Fishing, Golf, Horseback Riding, Hunting, Kayaking, Sailing, Shopping, Swimming, Tennis, Watersports
Vacation Bed & Breakfast Description:
-
-
Cities:
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Listonburg, PA (704)
Preston, MD (704)
Still Pond, MD (704)
Mc Henry, MD (481)
Saint Michaels, MD (262)
Oakland, MD (78)
Easton, MD (72)
Swanton, MD (55)
Cambridge, MD (50)
Chestertown, MD (50)
Price, MD (47)
Tilghman, MD (46)
Rock Hall, MD (32)
Oxford, MD (22)
Grantsville, MD (20)
Stevensville, MD (20)
Farmington, PA (14)
Royal Oak, MD (11)
Grasonville, MD (10)
Confluence, PA (9)
Bruceton Mills, WV (7)
Frostburg, MD (7)
Ohiopyle, PA (7)
Springs, PA (7)
Accident, MD (5)
Wingate, MD (5)
Denton, MD (4)
Friendsville, MD (4)
Jennings, MD (4)
Mount Savage, MD (4)
Queenstown, MD (4)
Sherwood, MD (4)
Betterton, MD (3)
Kingwood, WV (3)
Neavitt, MD (3)
Church Creek, MD (2)
Claiborne, MD (2)
Crellin, MD (2)
Elk Garden, WV (2)
Taylors Island, MD (2)
Wittman, MD (2)
Woolford, MD (2)
Bozman, MD (1)
Centreville, MD (1)
Chester, MD (1)
Kitzmiller, MD (1)
Markleysburg, PA (1)
Mcdaniel, MD (1)
Trappe, MD (1)
Ursina, PA (1)
Westernport, MD (1)
How to get there:
You may check resources for cheap airline tickets,
or if you need Chestertown, MD car service or Chestertown, MD airport transportation and limousine rental do not forget to register and receive special 10% discount code.
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