Vacation rentals in Talbot County

Carolina Cottage - 2 story, pet-free home

A home away from home! From the 2 car garage to the oversized deck, large master suite, and large yard, there is plenty of room for everyone to spread out and enjoy themselves. Take a walk to the neighborhood beach for some unbelievable sunsets, make a meal in the fully stocked kitchen, eat together at the large dining table, play board games, listen to the record player, play corn hole, or ride the bikes. Don't miss the many amazing restaurants! There is plenty to see and do on the Island.

Relax by the Water - Summer Dates Available!

STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacation experience. Fabulous location with panoramic views of the water everywhere you look. Crab and fish from the dock. Hop on a bike and explore the island by land and then try out kayaks for a water adventure. Cool off with an afternoon dip in the pool. Enjoy starry nights at the waterfront firepit. If the bikes and kayaks wore you out relax your muscles in the hot tub. Perfect!

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. Bring your kayak, paddleboard, or boat and enjoy all Cambridge has to offer or just sit on the end of the pier to watch the sunrise or sunset.

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Cottage #8 Herons Nest Lg 2 rooms Under Main House

OPEN March 25th to Nov 1st. every year. Herons Nest no 8 is located under main house, consist of full Kitchen, dining table, 1 queen size bed in separate bedroom, Living room Full size Futon open to a bed, 2 large sleeper recliners. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! room tax 4% due on arrival , 6% Abb collects please Bring waters . Boat info below. If need air mattress can bring.

Waterfront Cottage Retreat on 18 Acre Farm, Pool

Our newly renovated point cottage is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court, dock & more! This cottage features a private porch to enjoy the sunset, fully-equipped kitchen and laundry in unit. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop & library! Quiet and remote but very close to both Easton and Saint Michaels.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!