Holiday rentals near South Chesapeake City Historic District
We found 350 holiday rentals — enter your dates for availability
Choose the right holiday rental that's close to South Chesapeake City Historic District. Holiday homes provide the best amenities for you and your friends, family or even pets, such as air conditioning and a pool. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - South Chesapeake City Historic District
Showing deals for:10 Oct - 17 Oct
Image gallery for Waterfront:Panoramic Views/Hot Tub/ Pool/Sleeps 16 /Early check in/out off seaso
9.69.6 out of 10 rating
Exceptional
(162 reviews)
Waterfront:Panoramic Views/Hot Tub/ Pool/Sleeps 16 /Early check in/out off seaso
Elkton, MD
9% off
Price is AU$18,322
AU$18,322
AU$2,617 per night
includes taxes & fees
Image gallery for Vintage Waterfront Cottage with Stunning Sunsets
1010 out of 10 rating
Exceptional
(5 reviews)
Vintage Waterfront Cottage with Stunning Sunsets
North East, MD
8% off
Price is AU$4,569
AU$4,569
AU$653 per night
includes taxes & fees
Image gallery for Relaxing Ranch Getaway near Christiana Mall & University of Delaware!
1010 out of 10 rating
Exceptional
(6 reviews)
Relaxing Ranch Getaway near Christiana Mall & University of Delaware!
Bear, DE
5% off
Price is AU$4,971
AU$4,971
AU$710 per night
includes taxes & fees
Image gallery for Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark, DE
24% off
Price is AU$2,730
AU$2,730
AU$390 per night
includes taxes & fees
Image gallery for Quarry Landing - Center of Town & River View - 3 Bedroom
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit, MD
8% off
Price is AU$2,050
AU$2,050
AU$293 per night
includes taxes & fees
Image gallery for Waterfront house with amazing views. Top of the Chesapeake
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront house with amazing views. Top of the Chesapeake
Perryville, MD
8% off
Price is AU$4,656
AU$4,656
AU$665 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage with Private Boat Dock
1010 out of 10 rating
Exceptional
(8 reviews)
Charming Waterfront Cottage with Private Boat Dock
North East, MD
18% off
Price is AU$3,037
AU$3,037
AU$434 per night
includes taxes & fees
Image gallery for Private Waterfront Estate with Pool, Private Beach and Dock
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Private Waterfront Estate with Pool, Private Beach and Dock
Earleville, MD
9% off
Price is AU$21,873
AU$21,873
AU$3,125 per night
includes taxes & fees
Image gallery for A European styled retreat on Marylands Eastern Shore with Private pool
9.89.8 out of 10 rating
Exceptional
(76 reviews)
A European styled retreat on Marylands Eastern Shore with Private pool
Warwick, MD
8% off
Price is AU$3,550
AU$3,550
AU$507 per night
includes taxes & fees
Image gallery for Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Galena, MD
8% off
Price is AU$6,915
AU$6,915
AU$988 per night
includes taxes & fees
Image gallery for BEACH WITHOUT THE BUSTLE
1010 out of 10 rating
Exceptional
(30 reviews)
BEACH WITHOUT THE BUSTLE
Betterton, MD
8% off
Price is AU$2,476
AU$2,476
AU$354 per night
includes taxes & fees
Image gallery for Historic Creekside Home - 2br 2.5ba - Downtown North East
1010 out of 10 rating
Exceptional
(30 reviews)
Historic Creekside Home - 2br 2.5ba - Downtown North East
North East, MD
7% off
Price is AU$2,528
AU$2,528
AU$361 per night
includes taxes & fees
Image gallery for Luxurious and spacious townhome with all necessary amenities awaits your stay.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Middletown, DE
13% off
Price is AU$1,882
AU$1,882
AU$269 per night
includes taxes & fees
Image gallery for Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
1010 out of 10 rating
Exceptional
(54 reviews)
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Chesapeake City, MD
8% off
Price is AU$9,675
AU$9,675
AU$1,382 per night
includes taxes & fees
Image gallery for Private Suite w/Kitchenette
1010 out of 10 rating
Exceptional
(9 reviews)
Private Suite w/Kitchenette
Port Deposit, MD
12% off
Price is AU$1,480
AU$1,480
AU$211 per night
includes taxes & fees
Image gallery for A cottage on the shore of the Delaware River
9.89.8 out of 10 rating
Exceptional
(61 reviews)
A cottage on the shore of the Delaware River
Salem, NJ
8% off
Price is AU$2,585
AU$2,585
AU$369 per night
includes taxes & fees
Image gallery for Beachfront Sunsets on the Water at Oakwood Beach
1010 out of 10 rating
Exceptional
(36 reviews)
Beachfront Sunsets on the Water at Oakwood Beach
Salem, NJ
8% off
Price is AU$4,805
AU$4,805
AU$686 per night
includes taxes & fees
Image gallery for Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton, MD
12% off
Price is AU$3,909
AU$3,909
AU$558 per night
includes taxes & fees
Image gallery for Cozy cottage close to it all in Wilmington
1010 out of 10 rating
Exceptional
(57 reviews)
Cozy cottage close to it all in Wilmington
Wilmington, DE
8% off
Price is AU$1,718
AU$1,718
AU$245 per night
includes taxes & fees
Image gallery for Short Term Water Oriented Furnished Apartment
1010 out of 10 rating
Exceptional
(27 reviews)
Short Term Water Oriented Furnished Apartment
Elkton, MD
16% off
Price is AU$1,773
AU$1,773
AU$253 per night
includes taxes & fees
Image gallery for Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Havre De Grace, MD
8% off
Price is AU$1,429
AU$1,429
AU$204 per night
includes taxes & fees
Image gallery for Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
1010 out of 10 rating
Exceptional
(83 reviews)
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
North East, MD
8% off
Price is AU$4,569
AU$4,569
AU$653 per night
includes taxes & fees
Image gallery for Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Havre De Grace, MD
8% off
Price is AU$3,086
AU$3,086
AU$441 per night
includes taxes & fees
Image gallery for WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.89.8 out of 10 rating
Exceptional
(41 reviews)
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Earleville, MD
8% off
Price is AU$1,595
AU$1,595
AU$228 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - South Chesapeake City Historic District
STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Chesapeake Bay House with Dock & Private Beach
Sleeps 12 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
162 reviews(162 reviews)
Cozy private waterfront retreat
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Charming 2-bedroom cabin close to Fair Hill on horse farm
Sleeps 13 · 2 bedrooms · 2+ bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Top rated rentals - South Chesapeake City Historic District
Incredible view and hospitality!
1010 out of 10
Exceptionalexceptional
71 reviews(71 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