Chestertown, Maryland Vacation Rentals

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Location: Chestertown, MD undo
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Nightly Rate (median: 185)
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1 - 20 of about 418 from 10 sites
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Location:Delaware
Bedrooms:2
Sleeps:6
Property Type:Condo

Amenities:Cable/Satellite TV, Hot Tub, Microwave, No Pets, Restaurant, Swimming Pool, TV, Towels & more amenities »
Activities:Casino, Snow Skiing

Description: Termas de Chillán, the Andes Mountains' unrivaled Ski and Spa Resort, invites you to enjoy mountain magic and comfort immersed in breathtaking beauty. A style of service excellence that will make your stay an unforgettable ... more details »
Location:Delaware
Bedrooms:2
Bathrooms:2
Sleeps:5
Property Type:Apartment

Amenities:Cable/Satellite TV, Central heating, Kitchenette, No Pets, TV & more amenities »
Activities:Restaurants, Snow Skiing

Description: Valle Nevado offers several apartments for rent. Valle de Condores buildings one & two were recently inaugurated at Valle Nevado, and both are located on the south side of the parking area, just a one-minute ... more details »
Location:Delaware
Bedrooms:1
Bathrooms:1
Sleeps:4
Property Type:Condo

Amenities:Cable/Satellite TV, Hot Tub, Microwave, No Pets, Restaurant, Swimming Pool, TV, Towels & more amenities »
Activities:Casino, Snow Skiing

Description: Termas de Chillán, the Andes Mountains' unrivaled Ski and Spa Resort, invites you to enjoy mountain magic and comfort immersed in breathtaking beauty. A style of service excellence that will make your stay an unforgettable ... more details »
Location:Delaware
Bedrooms:1
Bathrooms:2
Sleeps:2
Property Type:Apartment

Amenities:Cable/Satellite TV, Central heating, Kitchenette, No Pets, TV & more amenities »
Activities:Restaurants, Snow Skiing

Description: Valle Nevado offers several apartments for rent. Valle de Condores buildings one & two were recently inaugurated at Valle Nevado, and both are located on the south side of the parking area, just a one-minute ... more details »
Location:Delaware
Bedrooms:1
Bathrooms:1
Sleeps:3
Property Type:Apartment

Amenities:Central heating, Kitchenette
Activities:Restaurants

Description: ... more details »
Location:Baltimore, Maryland
Bedrooms:3
Bathrooms:3
Sleeps:8
Property Type:Apartment

Amenities:Air Conditioning, Coffee Maker, Disability Access, Dishwasher, Full kitchen, Garage, Laundry, Lounge, Microwave, Oven, Pets OK, Pool Table, Refrigerator, Restaurant, Smoking OK & more amenities »
Activities:Casino, Gym, Shopping

Description: Luxurious 3 bedroom 3 bathroom vacation apartment fully furnished. 5 min walk from the inner harbor, downtown area, and convention center. all new furniture recently furnished amenities include a gym and a Lounge area with ... more details »
Location:Saint Michaels, Maryland
Bedrooms:5
Bathrooms:4
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, VCR & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Sailing, Shopping, Tennis & more activities »

Description: Tidewater Vacations in St Michaels is excited to present the Virginia (also known as Duxbury Point Manor as one of our more popular vacation homes on the water near St Michaels This enchanting Manor home ... more details »
Location:Saint Michaels, Maryland
Bedrooms:6
Bathrooms:5
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Beach, Boating, Fishing, Golf, Kayaking, Shopping & more activities »

Description: Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront home. Only minutes from the famous historic Chestertown, this magnificent 1000 acre estate is both a wildlife sanctuary and arboretum, with hundreds of mature ... more details »
Location:Saint Michaels, Maryland
Bedrooms:5
Bathrooms:4
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Cable/Satellite TV, Coffee Maker, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Shopping

Description: Tidewater Vacations of St Michaels presents a historic, charming vacation rental just minutes from Easton and St Michaels. Savanna is truly one of Marylands oldest and most picturesque vacation rental homes on the Miles River ... more details »
Location:Grasonville, Maryland
Bedrooms:4
Bathrooms:3
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Balcony, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Hot Tub, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Amusement Parks, Beach, Biking, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Racquetball, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis, Theme Parks, Volleyball, Water Parks, Water Skiing, Windsurfing, Zoo & more activities »

Description: Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 ... more details »
Location:Cambridge, Maryland
Bedrooms:3
Bathrooms:1
Sleeps:5
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, Coffee Maker, DVD Player, Deck, Dishwasher, Full kitchen, Hot Tub, Microwave, Oven, Pets OK, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Swimming Pool, TV, Toaster, VCR & more amenities »
Activities:Fishing, Golf, Gym, Sailing, Shopping, Tennis, Zoo & more activities »

Description: The Cottage at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres ... more details »
Location:Phoenix, Maryland
Bedrooms:3
Bathrooms:4
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Blender, Cable/Satellite TV, Coffee Maker, Computer Access, DVD Player, Dishwasher, Fireplace, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, TV, Toaster, VCR & more amenities »
Activities:Boating, Bowling, Canoeing, Casino, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Shopping, Zoo & more activities »

Description: The Space A unique and private single family home in a rural setting with views of nearby reservoir and forest preserve. Generous room sizes with private bathrooms are filled with natural light. Open kitchen, living ... more details »
Location:Saint Michaels, Maryland
Bedrooms:5
Bathrooms:4
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, VCR & more amenities »
Activities:Boating, Fishing, Golf, Gym, Kayaking, Shopping & more activities »

Description: Another luxury vacation rental home by Tidewater Vacations Inc on the Eastern Shore. This gorgeous, traditional country home is nestled amongst trees on magnificent grounds overlooking the Wye River.The secluded estate is ideally located close ... more details »
Location:Bowie, Maryland
Bedrooms:6
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Balcony, Basketball Court, CD Player, Cable/Satellite TV, DVD Player, Deck, Dishwasher, Fireplace, Foosball Table, Full kitchen, Laundry, Linens, Microwave, Pets OK, Phone, Refrigerator, Restaurant, Sauna, Shower, Smoking OK, Stereo, Swimming Pool, TV, VCR & more amenities »
Activities:Basketball, Fishing, Golf, Gym, Jetskiing, Shopping, Snorkeling, Surfing, Tennis, Theme Parks, Water Skiing, Zoo & more activities »

Description: Beautiful home in maintained private and gated community in the Washington DC area . 2 fully equipped kitchen with all amenities and appliances . Metro , 6 flags , Washington DC , Baltimor , Annapolis ... more details »
Location:Lewes, Delaware
Bedrooms:4
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Garage, Hair Dryer, Internet Access, Iron, Laundry, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Wireless Internet Access & more amenities »
Activities:Beach, Fishing, Golf, Gym, Hiking, Miniature Golf, Shopping, Tennis, Windsurfing & more activities »

Description: A large and newly furnished 4 bedroom house with 3.5 baths. Master bedroom suite with its own large bath plus 2 walk-in closets is located on the first floor. The house offers all the amenities ... more details »
Location:Chester, Maryland
Bedrooms:4
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Hot Tub, Internet Access, Kitchenette, Laundry, Linens, Microwave, Oceanfront, Oven, Pets OK, Refrigerator, Restaurant, Smoking OK, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Beach, Boating, Bowling, Canoeing, Casino, Fishing, Golf, Gym, Hiking, Horseback Riding, Jetskiing, Kayaking, Miniature Golf, Racquetball, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis & more activities »

Description: Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 bathrooms, one large family room with open kitchen, ... more details »
Location:Saint Michaels, Maryland
Bedrooms:6
Bathrooms:7
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Pool Table, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Swimming Pool, TV & more amenities »
Activities:Shopping

Description: Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront vacation home. This is where your dreams come true! Your vacation begins with a drive down a country lane surrounded by farmland or perhaps ... more details »
Location:Centreville, Maryland
Bedrooms:4
Bathrooms:2
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, Cable/Satellite TV, Coffee Maker, Dishwasher, Fireplace, Full kitchen, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Hiking, Shopping, Swimming & more activities »

Description: This house is on the estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own ... more details »
Location:Oxon Hill, Maryland
Bedrooms:2
Bathrooms:2
Sleeps:8
Property Type:Condo

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Computer Access, DVD Player, Disability Access, Dishwasher, Full kitchen, Hair Dryer, Hot Tub, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Pool Table, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Amusement Parks, Basketball, Casino, Kayaking, Ping Pong, Rafting, Restaurants, Shopping, Zoo & more activities »

Description: Our unique, spacious 2bdrm condo is located in vibrate National Harbor close to the sites in Washington, DC, premium shopping at Tanger Outlets, exotic restaurants and activities galore for all ages! National Harbor is home ... more details »
Location:Saint Michaels, Maryland
Bedrooms:3
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Balcony, Beachfront View, Blender, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Full kitchen, Internet Access, Laundry, Linens, Microwave, Oceanfront, Outdoor Shower, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Beach, Boating, Bowling, Fishing, Golf, Gym, Horseback Riding, Hunting, Ice Skating, Kayaking, Sailing, Shopping, Snorkeling, Tennis, Water Skiing & more activities »

Description: Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed ... more details »
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