Holiday rentals near Chesapeake Bay Bridge
We found 1,053 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:10 Oct - 17 Oct
Image gallery for Grace Cottage, Saint Michaels Walk to everything!
1010 out of 10 rating
Exceptional
(9 reviews)
Grace Cottage, Saint Michaels Walk to everything!
St. Michaels, MD
8% off
Price is NZ$7,333
NZ$7,333
NZ$1,048 per night
includes taxes & fees
Image gallery for Spacious 4 Bedroom Home w/ Hot Tub
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Spacious 4 Bedroom Home w/ Hot Tub
Edgewater, MD
7% off
Price is NZ$9,062
NZ$9,062
NZ$1,295 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
(47 reviews)
Secluded Waterfront Property on 3 acres with swimming pool and dock.
Bozman, MD
5% off
Price is NZ$10,103
NZ$10,103
NZ$1,443 per night
includes taxes & fees
Image gallery for Rare find! Chic cottage, salt water heated pool May 15-Oct15.
1010 out of 10 rating
Exceptional
(50 reviews)
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Arnold, MD
12% off
Price is NZ$9,757
NZ$9,757
NZ$1,394 per night
includes taxes & fees
Image gallery for 3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
1010 out of 10 rating
Exceptional
(33 reviews)
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Crownsville, MD
8% off
Price is NZ$40,275
NZ$40,275
NZ$5,754 per night
includes taxes & fees
Image gallery for HGTV quality, private guest suite, country getaway with hot tub & fire pit
1010 out of 10 rating
Exceptional
(5 reviews)
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville, MD
8% off
Price is NZ$3,756
NZ$3,756
NZ$537 per night
includes taxes & fees
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is NZ$4,855
NZ$4,855
NZ$694 per night
includes taxes & fees
Image gallery for Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
1010 out of 10 rating
Exceptional
(75 reviews)
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Stevensville, MD
8% off
Price is NZ$11,348
NZ$11,348
NZ$1,621 per night
includes taxes & fees
Image gallery for Bay views with kayaks, bikes, fire pit, crabbing and more
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side, MD
33% off
Price is NZ$4,400
NZ$4,400
NZ$629 per night
includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is NZ$3,554
NZ$3,554
NZ$508 per night
includes taxes & fees
Image gallery for Studio in Downtown – Walk to Everything!
1010 out of 10 rating
Exceptional
(19 reviews)
Studio in Downtown – Walk to Everything!
St. Michaels, Maryland
12% off
Price is NZ$3,346
NZ$3,346
NZ$478 per night
includes taxes & fees
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
7% off
Price is NZ$13,930
NZ$13,930
NZ$1,990 per night
includes taxes & fees
Image gallery for Waterfront Sunset Bayview: sleeps 6
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront Sunset Bayview: sleeps 6
Chester, MD
8% off
Price is NZ$5,330
NZ$5,330
NZ$761 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex
1010 out of 10 rating
Exceptional
(88 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is NZ$9,179
NZ$9,179
NZ$1,311 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$4,389
NZ$4,389
NZ$627 per night
includes taxes & fees
Image gallery for Want to get away? Staying with us. Very relaxing.
8.88.8 out of 10 rating
Excellent
(11 reviews)
Want to get away? Staying with us. Very relaxing.
Pasadena, MD
11% off
Price is NZ$2,695
NZ$2,695
NZ$385 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
(53 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville, MD
8% off
Price is NZ$6,572
NZ$6,572
NZ$939 per night
includes taxes & fees
Image gallery for Welcome to our newly built house
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Welcome to our newly built house
Glen Burnie, MD
8% off
Price is NZ$4,890
NZ$4,890
NZ$699 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
11% off
Price is NZ$4,876
NZ$4,876
NZ$697 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
(45 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is NZ$2,989
NZ$2,989
NZ$427 per night
includes taxes & fees
Image gallery for Kent Island Luxury Waterfront
1010 out of 10 rating
Exceptional
(6 reviews)
Kent Island Luxury Waterfront
Stevensville, MD
17% off
Price is NZ$9,126
NZ$9,126
NZ$1,304 per night
includes taxes & fees
Image gallery for Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side, MD
8% off
Price is NZ$15,008
NZ$15,008
NZ$2,144 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
(113 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is NZ$2,882
NZ$2,882
NZ$412 per night
includes taxes & fees
Image gallery for Dollhouse in Central Historic St Michaels
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Dollhouse in Central Historic St Michaels
St. Michaels, MD
12% off
Price is NZ$3,533
NZ$3,533
NZ$505 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Chesapeake Bay Bridge
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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
211 reviews(211 reviews)
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Sleeps 6 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
WATERFRONT right on a BEACH
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
The Heron's Nest at Atlantic Marina
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
293 reviews(293 reviews)
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 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