Holiday rentals near Historical Society of Talbot County
We found 351 holiday rentals — enter your dates for availability
If you'd like to stay close to Historical Society of Talbot County, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. At the end of the day, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Historical Society of Talbot County
Showing deals for:25 Jul - 1 Aug
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is NZ$11,424
NZ$11,424
NZ$1,632 per night
includes taxes & fees
Image gallery for Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
1010 out of 10 rating
Exceptional
(118 reviews)
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester, MD
8% off
Price is NZ$5,275
NZ$5,275
NZ$754 per night
includes taxes & fees
Image gallery for A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
1010 out of 10 rating
Exceptional
(18 reviews)
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Easton, MD
8% off
Price is NZ$5,509
NZ$5,509
NZ$787 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(40 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$8,458
NZ$8,458
NZ$1,208 per night
includes taxes & fees
Image gallery for Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
1010 out of 10 rating
Exceptional
(6 reviews)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
St. Michaels, MD
17% off
Price is NZ$5,146
NZ$5,146
NZ$735 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(27 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$13,141
NZ$13,141
NZ$1,877 per night
includes taxes & fees
Image gallery for 25-50% Off~Private Beach~Hot Tub~Fire Table~
1010 out of 10 rating
Exceptional
(22 reviews)
25-50% Off~Private Beach~Hot Tub~Fire Table~
Stevensville, MD
8% off
Price is NZ$8,819
NZ$8,819
NZ$1,260 per night
includes taxes & fees
Image gallery for Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
East New Market, MD
5% off
Price is NZ$13,607
NZ$13,607
NZ$1,944 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,424
NZ$11,424
NZ$1,632 per night
includes taxes & fees
Image gallery for Charming cottage along water with private pier, near St. Michaels Winery
9.69.6 out of 10 rating
Exceptional
(132 reviews)
Charming cottage along water with private pier, near St. Michaels Winery
Bozman, MD
12% off
Price is NZ$3,485
NZ$3,485
NZ$498 per night
includes taxes & fees
Image gallery for Cheerful three-bedroom Cottage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cheerful three-bedroom Cottage
Cambridge, MD
8% off
Price is NZ$3,079
NZ$3,079
NZ$440 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman, MD
8% off
Price is NZ$3,177
NZ$3,177
NZ$454 per night
includes taxes & fees
Image gallery for Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Jellyfish Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
Tilghman, MD
12% off
Price is NZ$5,438
NZ$5,438
NZ$777 per night
includes taxes & fees
Image gallery for "Point of View" Waterfront cottage with panoramic views on Tilghman Island
1010 out of 10 rating
Exceptional
(8 reviews)
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman, MD
9% off
Price is NZ$4,295
NZ$4,295
NZ$614 per night
includes taxes & fees
Image gallery for Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
9.49.4 out of 10 rating
Exceptional
(126 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
St. Michaels, MD
8% off
Price is NZ$8,934
NZ$8,934
NZ$1,276 per night
includes taxes & fees
Image gallery for A little slice of heaven on the Choptank River Sept 19 to 23 is now open
1010 out of 10 rating
Exceptional
(22 reviews)
A little slice of heaven on the Choptank River Sept 19 to 23 is now open
East New Market, MD
8% off
Price is NZ$4,179
NZ$4,179
NZ$597 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
1010 out of 10 rating
Exceptional
(93 reviews)
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Royal Oak, MD
8% off
Price is NZ$6,119
NZ$6,119
NZ$874 per night
includes taxes & fees
Image gallery for Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
Sherwood, MD
8% off
Price is NZ$2,052
NZ$2,052
NZ$293 per night
includes taxes & fees
Image gallery for Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.89.8 out of 10 rating
Exceptional
(124 reviews)
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge, MD
8% off
Price is NZ$8,197
NZ$8,197
NZ$1,171 per night
includes taxes & fees
Image gallery for Harbor View Suite
1010 out of 10 rating
Exceptional
(19 reviews)
Harbor View Suite
St. Michaels, MD
5% off
Price is NZ$3,565
NZ$3,565
NZ$509 per night
includes taxes & fees
Image gallery for Gorgeous Creek Side Ranch-Style Estate With Dock
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Gorgeous Creek Side Ranch-Style Estate With Dock
Queenstown, Maryland
7% off
Price is NZ$7,655
NZ$7,655
NZ$1,094 per night
includes taxes & fees
Image gallery for Relax on Kent Island in 3 Bedroom Home w/Waterview
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Relax on Kent Island in 3 Bedroom Home w/Waterview
Stevensville, MD
8% off
Price is NZ$4,910
NZ$4,910
NZ$701 per night
includes taxes & fees
Image gallery for Casa Maria heart of downtown Cambridge Maryland
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Casa Maria heart of downtown Cambridge Maryland
Cambridge, MD
8% off
Price is NZ$2,222
NZ$2,222
NZ$317 per night
includes taxes & fees
Image gallery for Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.69.6 out of 10 rating
Exceptional
(118 reviews)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
St. Michaels, MD
8% off
Price is NZ$4,110
NZ$4,110
NZ$587 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Historical Society of Talbot County
An Afternoon Nap in the Hammock is a Must.
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Cass-N-Reel Luxury Houseboat
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Stay in the HEART of Saint Michaels!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
342 reviews(342 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Sleeps 9 · 6 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
126 reviews(126 reviews)
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
St. Michael's Premier In-Town Rental with heated pool-opens 4/11/2025
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
134 reviews(134 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value