
Holiday rentals near Historical Society of Talbot County
We found 1,161 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental that's close to Historical Society of Talbot County. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as a garden and pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Historical Society of Talbot County
Showing deals for:14 Nov - 21 Nov
Image gallery for Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

1010 out of 10 rating
Exceptional
(10 reviews)
Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
North Beach, MD
16% off
Price is NZ$7,035
NZ$7,035
NZ$1,005 per night
includes taxes & fees
Image gallery for Edgewater/Mayo Gateaway w/ Hot Tub

9.89.8 out of 10 rating
Exceptional
(21 reviews)
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater, MD
7% off
Price is NZ$6,226
NZ$6,226
NZ$889 per night
includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland

9.89.8 out of 10 rating
Exceptional
(37 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is NZ$3,596
NZ$3,596
NZ$514 per night
includes taxes & fees
Image gallery for Secluded Waterfront Property on 3 acres with swimming pool and dock.

1010 out of 10 rating
Exceptional
(48 reviews)
Secluded Waterfront Property on 3 acres with swimming pool and dock.
Bozman, MD
5% off
Price is NZ$10,355
NZ$10,355
NZ$1,479 per night
includes taxes & fees
Image gallery for Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

1010 out of 10 rating
Exceptional
(22 reviews)
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
St. Michaels, MD
12% off
Price is NZ$3,393
NZ$3,393
NZ$485 per night
includes taxes & fees
Image gallery for Unbelievable beach views for 6

1010 out of 10 rating
Exceptional
(8 reviews)
Unbelievable beach views for 6
North Beach, MD
8% off
Price is NZ$3,567
NZ$3,567
NZ$510 per night
includes taxes & fees
Image gallery for NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.89.8 out of 10 rating
Exceptional
(29 reviews)
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Annapolis, MD
12% off
Price is NZ$5,318
NZ$5,318
NZ$760 per night
includes taxes & fees
Image gallery for Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville, MD
17% off
Price is NZ$3,151
NZ$3,151
NZ$450 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
(121 reviews)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
St. Michaels, MD
8% off
Price is NZ$4,132
NZ$4,132
NZ$590 per night
includes taxes & fees
Image gallery for Waterfront Annapolis w/swimming pool & pier -July 20-26 available

1010 out of 10 rating
Exceptional
(47 reviews)
Waterfront Annapolis w/swimming pool & pier -July 20-26 available
Annapolis, MD
14% off
Price is NZ$5,546
NZ$5,546
NZ$792 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home

1010 out of 10 rating
Exceptional
(30 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,221
NZ$12,221
NZ$1,746 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
(129 reviews)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
St. Michaels, MD
8% off
Price is NZ$9,097
NZ$9,097
NZ$1,300 per night
includes taxes & fees
Image gallery for Private Waterfront Home w/ Pier and 2+ Acres!

1010 out of 10 rating
Exceptional
(85 reviews)
Private Waterfront Home w/ Pier and 2+ Acres!
Deale, MD
7% off
Price is NZ$6,268
NZ$6,268
NZ$895 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex

1010 out of 10 rating
Exceptional
(90 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is NZ$9,035
NZ$9,035
NZ$1,291 per night
includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.

9.89.8 out of 10 rating
Exceptional
(54 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville, MD
8% off
Price is NZ$6,639
NZ$6,639
NZ$948 per night
includes taxes & fees
Image gallery for Peaceful getaway convenient to local amenities including beach, boating & food

9.89.8 out of 10 rating
Exceptional
(116 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is NZ$2,921
NZ$2,921
NZ$417 per night
includes taxes & fees
Image gallery for Eastern Shore beach cottage get-away

1010 out of 10 rating
Exceptional
(136 reviews)
Eastern Shore beach cottage get-away
Rock Hall, MD
8% off
Price is NZ$3,963
NZ$3,963
NZ$566 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
(11 reviews)
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman, MD
9% off
Price is NZ$4,325
NZ$4,325
NZ$618 per night
includes taxes & fees
Image gallery for Island Life! Kent Island Waterfront with Pool-Bring your boat!

1010 out of 10 rating
Exceptional
(195 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville, MD
12% off
Price is NZ$5,548
NZ$5,548
NZ$793 per night
includes taxes & fees
Image gallery for Pet-Friendly Cottage – Ideal for Summer Getaways!

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Pet-Friendly Cottage – Ideal for Summer Getaways!
Tilghman, MD
11% off
Price is NZ$3,945
NZ$3,945
NZ$564 per night
includes taxes & fees
Image gallery for Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

1010 out of 10 rating
Exceptional
(48 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is NZ$3,030
NZ$3,030
NZ$433 per night
includes taxes & fees
Image gallery for Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!

9.89.8 out of 10 rating
Exceptional
(95 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is NZ$5,926
NZ$5,926
NZ$847 per night
includes taxes & fees
Image gallery for Quiet Relaxing Waterfront Suisse Chalet

9.69.6 out of 10 rating
Exceptional
(76 reviews)
Quiet Relaxing Waterfront Suisse Chalet
Annapolis, MD
18% off
Price is NZ$4,479
NZ$4,479
NZ$640 per night
includes taxes & fees
Image gallery for The heart of St Michaels awaits.

1010 out of 10 rating
Exceptional
(46 reviews)
The heart of St Michaels awaits.
St. Michaels, MD
7% off
Price is NZ$3,488
NZ$3,488
NZ$498 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
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
195 reviews(195 reviews)
Waterfront Getaway, Dock Your Boat & Play!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Sleeps 16 · 6 bedrooms · 4+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Floating 2 bed 2 bath condo stunning views of the bay
Sleeps 8 · 2 bedrooms · 2 bathrooms
6.86.8 out of 10
5 reviews(5 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