Showing 62 Vacation Rentals from Chestertown, MD

Amenities:
Air Conditioning, Alarm Clock, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Freezer, Full kitchen, Garage, Internet Access, Iron, Lakefront, Laundry, Microwave, Non-Smoking, Oceanfront, Oven, Patio, Pets OK, Phone, Refrigerator, Screened porch, Stereo, TV, Toaster, VCR

Activities:
Beach, Biking, Boating, Fishing, Golf, Hiking, Horseback Riding, Hunting, Restaurants, Shopping, Water Skiing

Vacation Home Description:
description:Fairlee Point offers all the comforts of home with the beautiful and relaxing environment of the Eastern Shore of Chesapeake Bay. It is situated on a bluff overlooking Fairlee Creek with a private dock and 3.5 acres of private land. Enjoy the house, the grounds and the water in your private piece of heaven. In addition to the Great Room overlooking the bay there is a 1200 sq ft deck and a screened porch. Summer, winter, fall or spring, Fairlee Point is the place to be when it is time to get off the wor...

Amenities:
Air Conditioning, Business Conference Center, Coffee Maker, Complimentary Continental Breakfast, Fireplace, Free Parking, Hair Dryer, Internet Access, Iron, Lounge, Modem Data Port Connection, Non-Smoking, Patio, Restaurant, Swimming Pool, TV

Activities:
-

Vacation Bed & Breakfast Description:
description:One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay in Maryland's Eastern Shore, eight miles from historic Chestertown. With large common rooms and beautifully appointed guest rooms, comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.

Amenities:
Air Conditioning, Business Conference Center, Coffee Maker, Complimentary Continental Breakfast, Free Parking, Hair Dryer, Internet Access, Iron, Lounge, Modem Data Port Connection, Non-Smoking, Restaurant, TV

Activities:
Restaurants

Vacation Bed & Breakfast Description:
description:The Brampton Bed and Breakfast Inn is a romantic oasis on Maryland’s Eastern Shore. Located on 25 wooded and landscaped acres, one mile outside the charming town of Chestertown, MD, our Chesapeake Bay Inn beautifully blends the grand elegance of a historical estate with the comfort and amenities today’s travelers demand. Ignite or rekindle romance in a spacious, private and well-appointed guest room or cottage at our Eastern Shore Bed and Breakfast, offering wood-burning fireplaces, whirlpool tubs and glorious views. Enjoy a full breakfast graciously served at individual tables in the beautiful dining room of our Eastern Shore Inn or our afternoon tea featuring delectable treats. Attention to detail, personal service, and friendly innkeepers will make your visit to our Romantic Maryland Getaway a memorable one. Nearby Chestertown is a wondrous colonial village with abundant activities, unique shops and great restaurants. Our Chestertown Bed and Breakfast is a great weekend getaway from Washington DC and serves as a perfect base for exploring all that the Eastern Shore has to offer. Brampton Inn was the only Bed and Breakfast in Maryland selected by National Geographic Traveler for it’s first-ever, annual “Stay List”. The editor’s list, which debuted in April 2008, includes just 150 properties in the United States, Canada, and the Caribbean. St. Michaels and Annapolis are an easy one-hour drive from the inn.

Amenities:
Air Conditioning, Coffee Maker, DVD Player, Internet Access, Laundry, Linens, Microwave, Non-Smoking, Pets OK, Phone, Refrigerator, Restaurant, Stove, TV

Activities:
Boating, Canoeing, Fishing, Hunting, Kayaking

Vacation Home Description:
description:Boxer's Rest is an 85 acre working farm and nature retreat on the Chesapeake Country Scenic Byway near Historic Chestertown on the Eastern Shore of Maryland. The property was purchased in 2007 by Jonathan and Lori Sallet who have placed it under a conservation easement with the Eastern Shore Land Conservancy. The easement protects the property in perpetuity from development. It will forever be maintained as farmland and natural habit and as a beautiful part of the Eastern Shore's rural landscape. The farm is being converted to organic farming. The process will begin in the fall of 2008 when the farming operation will cease using chemical fertilizers and pesticides. The land will be put into hay and grass production for the three years required by the USDA to clear the soil of the inorganic matter. Once certified, this farm will produce organic feed for local organic dairies and livestock farms. The Cottage at Boxer's Rest is a little European stone and stucco getaway with vaulted cedar ceilings and sky lights nestled in the 22 acre forest on the Pond on Hambleton Creek. A vacation home for the Sallets and selectively rented to friends looking for an escape from the hectic urban life and time away from the phone, TV and internet, the cottage is a perfect romantic, writing, reading, thinking or meditation retreat. The 85 acres surrounding the cottage allows visitors privacy and serenity for walking and nature watching. Just five minutes from Boxer's Rest, Chestertown is a charming historic town. Its distinctions include being named one of America's Dozen Distinctive Destinations by the National Trust for Historic Preservation and regular features in the Washington Post, Baltimore Sun and Baltimore Magazine and Washingtonian Magazine. Its brick sidewalk and cobble stone streets are lined with antique shops and art galleries, specialty stores and sidewalk cafes.

Amenities:
Air Conditioning, Alarm Clock, Cable/Satellite TV, Ceiling fans, Fireplace, Hair Dryer, Hot Tub, Kitchenette, Linens, Phone, Refrigerator, Stereo, Swimming Pool, Towels

Activities:
Biking, Horseback Riding, Movie Theaters, Restaurants, Shopping, Sightseeing, Swimming

Vacation Bed & Breakfast Description:
description:Come for a getaway to Great Oak, a Chesapeake Bay Maryland bed and breakfast where the only honking comes from the geese, where the closest highway is...

Amenities:
Air Conditioning, Cable/Satellite TV, Ceiling fans, DVD Player, Fireplace, Hair Dryer, Hot Tub, Kitchenette, Linens, Phone, Refrigerator, Stereo, Swimming Pool, Towels

Activities:
Beach, Biking, Boating, Diving, Fishing, Horseback Riding, Movie Theaters, Restaurants, Shopping, Sightseeing, Surfing, Swimming

Vacation Bed & Breakfast Description:
description:The Brampton Bed and Breakfast Inn is Marylands Eastern Shore romantic oasis, located on 20 wooded acres, just one mile outside the charming town of C...

Amenities:
Air Conditioning, Balcony, Cable/Satellite TV, Fireplace, Internet Access, Iron, Lounge, Non-Smoking, Oceanfront, Patio, Phone, Restaurant, Screened porch, Stereo, Swimming Pool, TV

Activities:
Beach, Biking, Bird watching, Boating, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Hunting, Sailing, Shopping, Swimming, Tennis

Vacation Bed & Breakfast Description:
description:Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century county-style estate rests on the waterfront of the Chesapeake Bay. With 12 questrooms, Great Oak offers the finest in a luxury bed and breakfast. Enjoy the most beautiful sunsets on the Eastern Shore from our private beach or our vast 12 acres of manicured lawns. As featured on The Today Show with travel editor Peter Greenberg, July 2005, and also featured in the February 2004 issue of Southern Living Magazine, in The Washingtonian 'Dream Weekends', April 2003, in Baltimore Magazine July 2003 'Bay Watch', in Chesapeake Life June 2003 issue, in Chesapeake Life 1999 winter edition 'Great Gatsby on the Chesapeake'. Recognized by American Historic Inns as one of their 'Top Ten Most Romantic Inns' for 2000. Approved by the Maryland Bed and Breakfast Association. Featured in Karen Brown's Travel Guide. Come for a getaway to Great Oak, a Chesapeake Bay Maryland bed and breakfast where the only honking comes from the geese, where the closest highway is the duck flyway, and where the only traffic you see from your room are the boaters sailing the crystal water of the Chesapeake Bay Waterfront just 200 yards away. Great Oak Manor, a Chesapeake Bay bed and breakfast, 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 12 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by. Each guest room of our Chesapeake Bay Bed and Breakfast is unique - from the grand Marmaduke Chesapeake Bay waterside room at the top of the spiral staircase to quaint sloped ceiling rooms on the third floor. Each individually air conditioned and each with its own story to tell. The Bed and Breakfast Innfeatures an expansive terrace offering exquisite views of the Chesapeake Bay. Lounge chairs are provided for those who wish to cozy up with a book or to just sit and watch the sunset. Great Oak Manor...

Amenities:
Phone

Activities:
-

Vacation Bed & Breakfast Description:
description:This pristine 18th-century manor house sits as a jewel on 10 acres overlooking Stoneybrook Pond. The six guest rooms, with parlors and numerous fireplaces, provide a casual and friendly atmosphere. Handsome polished wide-board floors add to the colonial decor. The Inn at Mitchell House is a popular setting for romantic weddings, small corporate meetings and other events. We will assist you in all of your organizational needs. Rates for the rooms include a full country breakfast, based upon two guests per room.

Amenities:
Phone

Activities:
-

Vacation Bed & Breakfast Description:
description:The Brampton Bed and Breakfast Inn is Maryland’s Eastern Shore romantic oasis, located on 20 wooded acres, just one mile outside the charming town of Chestertown, Maryland. Brampton B&B Inn brilliantly blends the grand elegance of a historical estate with the comfort and modern amenities today's stressed-out travelers crave. Ignite or rekindle romance in one of our spacious and well-appointed guest rooms, offering wood-burning fireplaces, whirlpool tubs and glorious views.

Amenities:
-

Activities:
-

Vacation Bed & Breakfast Description:
description:The White Swan Tavern has been a familiar landmark in Chestertown since pre-Revolutionary War days. Not far from the great Eastern cities, it is an unexpectedly quiet, elegant place nestled in the history of Maryland''s Eastern Shore. The White Swan is for those who treasure serene streets, birdsong mornings, impeccable service, and the grace of New World Tradition.

Amenities:
Air Conditioning, CD Player, Ceiling fans, Fireplace, Internet Access, Iron, Ironing Board, No Pets, Non-Smoking, Patio, Phone, Swimming Pool, TV

Activities:
Beach, Biking, Bird watching, Golf, Hiking, Historical Sites, Horseback Riding, Movie Theaters, Restaurants, Shopping, Tennis

Vacation Bed & Breakfast Description:
-

Amenities:
Phone

Activities:
Beach, Bird watching, Hiking, Historical Sites, Horseback Riding, Movie Theaters, Restaurants, Shopping, Tennis

Vacation Bed & Breakfast Description:
-

Amenities:
Phone

Activities:
Hunting, Sailing, Shopping

Vacation Bed & Breakfast Description:
description:Much like the heritage of the Claddaugh ring, the Claddaugh Farm Bed and Breakfast is steeped in tradition as well. Nestled midst gentle Queen Anne's county farmlands, this stately turn-of-the-century farmhouse is an inviting stop for Eastern Shore Travelers. During your stay, you'll be tempted to spend your time sailing along the historic Chestertown water-front, hunting in the amply stocked Maryland game lands, shopping at many quaint collectible shops around town, or relaxing with a book on a leisurely conversation in the parlor by a warming fire. Parlor Front Porch We extend a gracious invitation to come and enjoy our home and all that the area has to offer.

Amenities:
Phone

Activities:
Hunting

Vacation Bed & Breakfast Description:
description:We are committed to providing our guests with the best we have to offer, surpassing guest expectations. Unwind and relax at this respectable 28-room Inn, conveniently located in peaceful Chestertown, a historic colonial town by the sparkling waters of the Chester River.

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

Activities:
Beach, Biking, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Massage, Museums, Shopping, Swimming, Tennis, Watersports

Vacation Bed & Breakfast Description:
description:This property has 12 total guest accommodations with private bath, 5 with fireplaces, 3 two-bedroom suites and 2 conference rooms. The types of beds available include King and Queen.