Holiday rentals near Chesapeake Bay Bridge
We found 1,049 holiday rentals — enter your dates for availability
Choose the right holiday rental within easy reach of Chesapeake Bay Bridge. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chesapeake Bay Bridge
Showing deals for:15 Aug - 22 Aug
Image gallery for Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Davidsonville, MD
6% off
Price is NZ$14,944
NZ$14,944
NZ$2,135 per night
includes taxes & fees
Image gallery for Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Annapolis, MD
8% off
Price is NZ$7,913
NZ$7,913
NZ$1,130 per night
includes taxes & fees
Image gallery for Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
1010 out of 10 rating
Exceptional
(10 reviews)
Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
Pasadena, MD
8% off
Price is NZ$9,765
NZ$9,765
NZ$1,395 per night
includes taxes & fees
Image gallery for Escape Villa in Downtown Annapolis
1010 out of 10 rating
Exceptional
(7 reviews)
Escape Villa in Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$7,405
NZ$7,405
NZ$1,058 per night
includes taxes & fees
Image gallery for Waterfront Home on the Chesapeake Bay!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Waterfront Home on the Chesapeake Bay!
Shady Side, MD
8% off
Price is NZ$7,355
NZ$7,355
NZ$1,051 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$5,370
NZ$5,370
NZ$767 per night
includes taxes & fees
Image gallery for Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
1010 out of 10 rating
Exceptional
(8 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is NZ$3,427
NZ$3,427
NZ$490 per night
includes taxes & fees
Image gallery for Historic District"Crab Cakes and Football"
1010 out of 10 rating
Exceptional
(42 reviews)
Historic District"Crab Cakes and Football"
Annapolis, MD
8% off
Price is NZ$5,710
NZ$5,710
NZ$816 per night
includes taxes & fees
Image gallery for Recently Renovated Annapolis Home - Conveniently Located
1010 out of 10 rating
Exceptional
(60 reviews)
Recently Renovated Annapolis Home - Conveniently Located
Annapolis, MD
8% off
Price is NZ$7,250
NZ$7,250
NZ$1,036 per night
includes taxes & fees
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$11,630
NZ$11,630
NZ$1,661 per night
includes taxes & fees
Image gallery for NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
1010 out of 10 rating
Exceptional
(7 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Annapolis, MD
8% off
Price is NZ$18,926
NZ$18,926
NZ$2,704 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis, MD
8% off
Price is NZ$7,355
NZ$7,355
NZ$1,051 per night
includes taxes & fees
Image gallery for Location Location Location!!!50 Steps from Main Street and all of the action
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Location Location Location!!!50 Steps from Main Street and all of the action
Annapolis, MD
7% off
Price is NZ$5,244
NZ$5,244
NZ$749 per night
includes taxes & fees
Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
1010 out of 10 rating
Exceptional
(13 reviews)
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall, MD
16% off
Price is NZ$3,118
NZ$3,118
NZ$445 per night
includes taxes & fees
Image gallery for Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
1010 out of 10 rating
Exceptional
(7 reviews)
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Rock Hall, MD
8% off
Price is NZ$3,968
NZ$3,968
NZ$567 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
(92 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is NZ$6,110
NZ$6,110
NZ$873 per night
includes taxes & fees
Image gallery for Fisher House - Downtown Annapolis!
1010 out of 10 rating
Exceptional
(10 reviews)
Fisher House - Downtown Annapolis!
Annapolis, MD
7% off
Price is NZ$8,874
NZ$8,874
NZ$1,268 per night
includes taxes & fees
Image gallery for House w/Water Views of Rock Creek 2BA 2BA Cottage
1010 out of 10 rating
Exceptional
(27 reviews)
House w/Water Views of Rock Creek 2BA 2BA Cottage
Pasadena, MD
7% off
Price is NZ$3,128
NZ$3,128
NZ$447 per night
includes taxes & fees
Image gallery for Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
9.29.2 out of 10 rating
Wonderful
(34 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Annapolis, MD
8% off
Price is NZ$2,710
NZ$2,710
NZ$387 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,437
NZ$6,437
NZ$920 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
(41 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$8,695
NZ$8,695
NZ$1,242 per night
includes taxes & fees
Image gallery for Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
1010 out of 10 rating
Exceptional
(25 reviews)
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Queenstown, MD
17% off
Price is NZ$1,365
NZ$1,365
NZ$195 per night
includes taxes & fees
Image gallery for Beautiful Historic Home With Great Location!
1010 out of 10 rating
Exceptional
(120 reviews)
Beautiful Historic Home With Great Location!
Annapolis, MD
7% off
Price is NZ$6,507
NZ$6,507
NZ$930 per night
includes taxes & fees
Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis, MD
16% off
Price is NZ$10,448
NZ$10,448
NZ$1,493 per night
includes taxes & fees
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Find the best place to stay - Chesapeake Bay Bridge
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Sleeps 11 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
208 reviews(208 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Sleeps 14 · 5 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
Edgewater's Shelby on the Bay
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Sleeps 16 · 7 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 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