Guesthouse vacation rentals in Talbot County

Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory medium firm bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near the start of annual races and waterfront activities.

The Suite at Mostly Porches

This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including the Auto Museum, the Maritime Museum, the local YMCA and numerous restaurants. A stunning view of Saint Michaels Harbor, with the combination of work boats, powerboats sailboats and visiting yachts. Another view of the “Old Mill” which houses Lyons Distilling, the Winery, Eastern Shore Brewing, and numerous craft shops. You will be in a quiet corner of this maritime community.

The Place in Cambridge-Easing into winter

The pool is open through September 30th Beautifully located, a clean crisp poolhouse cottage with key extras.! Queen bed, full kitchenette, and beautiful bath. Enjoy the lovely in-ground pool & poolside seating. Perfect for couples or small families. A block from the Choptank River, 1/2 mile walk downtown to shops and dining. Experience the Eastern Shore of the Chesapeake from a new perspective-it's your stay! The Place in Cambridge, sometimes, the best experiences come in simple packages.

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Heide's GuestHouse

Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambridge. Visit the Harriet Tubman Museum, dine on fresh local seafood, or enjoy a leisurely stroll along the Choptank River — all just steps from your front door. Back home, rest and relax on the shared patio, or curled up in front of the TV. Traveling with a pet, or maybe a larger crew? Make use of this vacation rental's pet-friendly policy and additional rental home on-site.

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Two inflatable paddleboards, one inflatable kayak and one inflatable 2 seater kayak available for use. Limited size life jackets available.

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Waterfront-View of Bay from your Bed- Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Newly Renovated Guest House

Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Maryland. The house is in a quiet neighborhood with a beautiful view of Town Creek. Take a short walk or bike ride to town where you can enjoy fine dining and shopping. The house is equipped with TV, Wifi, AC to make your stay comfortable. There is reserved parking in front of the house and enjoy dining on the outside porch.

The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

"The Perch" - Studio Cottage - Chesapeake Bay

***Hot Tub on site*** ***Ramp Access (no stairs needed!)*** Go green at this unique property! NEWLY RENOVATED in 2025. Water and energy saving technology in full swing. Natural beauty, Zen vibe, steps from the Chesapeake Bay. Access to sandy beach, kayak, exclusive use of back deck, BBQ gas grill. Shower uses mini-tank technology for low water / energy consumption.