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Latest Vacation Rentals in Talbot County, MD

Photo for 4 Br Agritourism Vacation Rental In Bozman, Maryland

Bozman (10)

4 Br Agritourism Vacation Rental In Bozman, Maryland

STN-23-12This charming 16+ acre waterfront farmhouse circa 1769 just underwent a massive renovation and interior redesign for a beautiful Eastern Shore get-a-way. The house is situated adjacent to...

Created on Feb 21, 2024
Photo for 2 Br Private Vacation Home Vacation Rental In Claiborne, Maryland

Claiborne (1)

2 Br Private Vacation Home Vacation Rental In Claiborne, Maryland

STRN-23-22Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Eastern Shore of MD. Slow your pace and enjoy a leisurely bike ride into town or...

Created on Feb 21, 2024
Photo for 4 Br Private Vacation Home Vacation Rental In Easton, Maryland

Easton (42)

4 Br Private Vacation Home Vacation Rental In Easton, Maryland

Eastern Shore Vacation Rentals presents Sky View. The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is created by a sprawling interior and includes a separate dining room, large...

Created on Feb 21, 2024
Photo for 4 Br Private Vacation Home Vacation Rental In Mcdaniel, Maryland

Mcdaniel (1)

4 Br Private Vacation Home Vacation Rental In Mcdaniel, Maryland

Eastern Shore Vacation Rentals presents Oyster Cottage. Just a 10-minute drive from historic St. Michaels and Tilghman Island, Oyster Cottage offers the best of the Eastern Shore.This charming 4BR,...

Created on Feb 21, 2024
Photo for 6 Br Villa Vacation Rental In Neavitt, Maryland

Neavitt (8)

6 Br Villa Vacation Rental In Neavitt, Maryland

Summary:Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private dock (5ft MLW), boat slip, sun deck, waterside in-ground pool, pool houses, and...

Created on Feb 21, 2024
Photo for 3 Br Private Vacation Home Vacation Rental In St. Michaels, Maryland

Newcomb (2)

3 Br Private Vacation Home Vacation Rental In St.
Michaels, Maryland

Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginning of town. Fully renovated, with WI-Fi, there is a Master Bedroom with king...

Created on Feb 21, 2024
Photo for 4 Br Private Vacation Home Vacation Rental In Oxford, Maryland

Oxford (20)

4 Br Private Vacation Home Vacation Rental In Oxford, Maryland

Talbot County STR License# STRN-22-9Judith's Garden is a delightful home located off the beaten path, yet close to the historic town of Oxford. Boasting four spacious bedrooms on a single-level,...

Created on Feb 21, 2024
Photo for 4 Br Private Vacation Home Vacation Rental In Royal Oak, Maryland

Royal Oak (15)

4 Br Private Vacation Home Vacation Rental In Royal Oak, Maryland

Eastern Shore Vacation Rentals presents Family Tides. The impressive 4BR, 3.5BA waterfront along Irish Creek is designed with relaxation in mind. The ideal open floor plan concept features a...

Created on Feb 21, 2024
Photo for 3 Br Private Vacation Home Vacation Rental In Saint Michaels, Maryland

Saint Michaels (52)

3 Br Private Vacation Home Vacation Rental In Saint Michaels, Maryland

Charming Waterfront Cottage in St MichaelsBegin your day at Riverview Retreat with a beautiful sunrise and be amazed with a stunning sky at sunset. As soon as you enter this charming cottage you...

Created on Feb 21, 2024
Photo for 8 Br Private Vacation Home Vacation Rental In Sherwood, Maryland

Sherwood (8)

8 Br Private Vacation Home Vacation Rental In Sherwood, Maryland

TREMEZZO STAY - CHEASAPEAKE MANSIONOur properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.If you do not see availability for...

Created on Feb 21, 2024
Photo for 3 Br Private Vacation Home Vacation Rental In Tilghman, Maryland

Tilghman (27)

3 Br Private Vacation Home Vacation Rental In Tilghman, Maryland

Talbot County STR License #STN-22-20This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-filled interior and contains a first-floor bedroom and a flow-through...

Created on Feb 21, 2024
Photo for 1 Br Bed & Breakfast Vacation Rental In Trappe, Maryland

Trappe (9)

1 Br Bed & Breakfast Vacation Rental In Trappe, Maryland

B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal Telescopic Tidewater Style Bed & Breakfast called The Anchorage, circa 1800...

Created on Feb 21, 2024
Photo for 2 Br Cottage Vacation Rental In Wittman, Maryland

Wittman (8)

2 Br Cottage Vacation Rental In Wittman, Maryland

Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by mature majestic shade trees. Beautiful water views on 3 sides and facing west...

Created on Feb 21, 2024
Photo for 5 Br Private Vacation Home Vacation Rental In Wye Mills, Maryland

Wye Mills (1)

5 Br Private Vacation Home Vacation Rental In Wye Mills, Maryland

Cool waterfront contemporary with retro vibeLocated on the serene banks of Skipton & Mill Creeks, this home offers plenty of comforts disguised as contemporary cool. The open living area, situated...

Created on Feb 21, 2024
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