Apartment vacation rentals in Talbot County

4.94 out of 5 average rating, 17 reviews

Apartment in Annapolis

Crow’s Nest Cottage - Down Under: Chesapeake Bay

Crow’s Nest Cottage - Down Under: 3BR/1BA garden-level duplex with fenced Zen garden, natural bamboo, water fountain, gas BBQ grill, brand new gourmet kitchen, sleeps 8. TV in all BR’s, steps to Chesapeake Bay waterfront. Sandy beach, protected swimming lagoon, park, bbq grills & picnic tables. Enjoy coastal Maryland’s beautiful flora & fauna. Nature lovers paradise, lower-level duplex (5 steps down) in waterfront community, access to pier, boat ramp, kayaks. Best vacation rental holiday home

Superhost

4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

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”.

4.91 out of 5 average rating, 178 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.

Apartment in Stevensville

4.98 out of 5 average rating, 278 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.

4.97 out of 5 average rating, 34 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 walk or bike down the lane to explore quiet back roads and beautiful country scenery. A short 15 minute drive into the town of Cambridge offers unique shops and restaurants, sightseeing and nearby Blackwater Refuge.

5 out of 5 average rating, 12 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

This is a beautiful furnished water view one bedroom apartment located just 50 feet from the Choptank River and only a few blocks from 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, WiFi, TV, stereo, and washer/dryer.

4.97 out of 5 average rating, 93 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.

4.91 out of 5 average rating, 58 reviews

The heart of St Michaels awaits.

Nestled in the vibrant heart of the St. Michaels historic district, this stunning one-bedroom, one-and-a-half-bathroom flat invites you to experience the charm and culture of this quaint town right at your doorstep. Walk to exquisite dining experiences, unique local hangouts, boutique shops, enchanting galleries, and engaging museums. Enjoy the ease of a private parking space, but leave your car behind as everything you need is just a stroll away.

Cambridge Apt in Walkable Neighborhood

Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at this 1-bedroom, 1-bath vacation rental apartment in Cambridge, Maryland! Spend your days stepping back in time at the area's museums and historical sites, or book a boat tour and set sail on the Choptank River. After fun-filled days of exploration, head back to unwind in the comfort of this cozy abode. Book today!

4.78 out of 5 average rating, 67 reviews

Apartment in Wye Mills

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

This unique apartment above the 3 car garage sleeps 4 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.

4.85 out of 5 average rating, 20 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.