Apartment vacation rentals in Talbot County

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Top-rated apartment rentals in Talbot County

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Guest favorite

Rental unit in Cambridge

4.92 out of 5 average rating, 118 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Guest favorite

Rental unit in Saint Michaels

4.9 out of 5 average rating, 157 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

Guest favorite

Rental unit in Stevensville

4.98 out of 5 average rating, 272 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Guest favorite

Rental unit in Annapolis

4.93 out of 5 average rating, 15 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

MID-WEEK SPECIAL! Crow’s Nest Cottage - Down Under (3BR/1BA garden-level duplex) full kitchen, sleeps 10. Comfort & Style, vacation setting, steps from Chesapeake Bay waterfront. Sandy beach, protected swimming lagoon, park, bbq grills & picnic tables. Enjoy coastal Maryland’s beautiful flora and fauna. Nature lovers paradise, quaint lower-level duplex (5 steps down) in waterfront community, access to pier, boat ramp, kayaks and more. Vacation rental, rental home, holiday rental, Maryland.

Guest favorite

Private room in Saint Michaels

4.86 out of 5 average rating, 22 reviews

George Brooks House B&B # 2 Queen

Historic Inn 1/2 mile outside of the town - a fabulous colonial seaport with lots of retail shops and restaurants plus the Chesapeake Bay Maritime Museum. Our inn has won two prestigious local and state preservation awards. Featuring hand carved mahogany furniture with Queen or King beds, private bathrooms with tiled showers, full 3 course breakfast, swimming pool, hot tub and bikes. This is our Queen bedroom # 2 downstairs (12' by 15') with fireplace just off of our parlor and garden room.

Guest favorite

Rental unit in Cambridge

4.95 out of 5 average rating, 21 reviews

Happy Campers Waterfront Suite

Come and experience a relaxing getaway at our Waterfront Suite! Happy Campers is located near the corner of the Choptank River and the Chesapeake Bay, surrounded by acres of farm land. You will enjoy quiet days, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery. A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park.

Guest favorite

Rental unit in Saint Michaels

4.98 out of 5 average rating, 63 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Guest favorite

Rental unit in Saint Michaels

4.89 out of 5 average rating, 27 reviews

Fabulous Holiday getaway.

Located in the heart of historic St Michaels, this unique studio has a style all its own. Award winning restaurants, one of a kind boutiques, art galleries and local hot spots all within walking distance. Lovely and stylish S. Talbot 405 is the perfect weekend get away. Let us arrange for bikes and then you can cycle over and check out the harbor. Sunset cruise more to your taste? We can arrange that as well. Be one of the first to stay at this special property.

Guest favorite

Rental unit in Cambridge

5 out of 5 average rating, 11 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

This is a beautiful furnished water view one bedroom apartment located just a few blocks from Long Wharf and the Cambridge Yacht Club. This is the perfect location for visiting professionals, vacation escapes from the Baltimore/Washington area and for sports events like the Ironman. It has great views of the Choptank from almost every room. It is tastefully furnished with antiques, has a private deck with water view, has CAC and washer/dryer.

Guest favorite

Rental unit in Wye Mills

4.75 out of 5 average rating, 60 reviews

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

This unique apartment above the 3 car garage sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill which is still in operation as it has been since 1682! Come experience lakeside apartment living.

Rental unit in Cambridge

4.83 out of 5 average rating, 18 reviews

Cozy 3rd Floor Apartment in Historic West End

Freshly updated 1000 sq ft 3rd fl apt with birds eye view of the beautiful Choptank River. Located in the heart of the Historic District you are close to everything in town. Soho-like soaring ceilings... living/dining area, one bedroom, large kitchen & large bath. Full-sized washer/dryer. Cable TV and excellent WI-FI. Light and airy. Perfect for couple or single guest. Sorry no kids or pets.

Guest favorite

Rental unit in Saint Michaels

5 out of 5 average rating, 29 reviews

Saint Michaels Luxury Get Away

Welcome to Skinner Alley Flat. Newly renovated 3 BR apartment in the heart of the charming town of Saint Michaels. Located one block from Main Street, enjoy the character and convenience of being close to everything offered in this Eastern Shore historic community. Amazing restaurants only blocks away and plenty of shops to choose from. Easy drive from the DC metro area.