Holiday rentals near Chesapeake Exploration Center
We found 1,024 holiday rentals — enter your dates for availability
If you'd like to stay close to Chesapeake Exploration Center, take a look at private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include Wi-Fi and a hot tub. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chesapeake Exploration Center
Showing deals for:19 Sept - 26 Sept
Image gallery for Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
1010 out of 10 rating
Exceptional
(87 reviews)
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Royal Oak, MD
8% off
Price is AU$26,650
AU$26,650
AU$3,807 per night
includes taxes & fees
Image gallery for House near Patapsco River 2700 square feet
9.49.4 out of 10 rating
Exceptional
(13 reviews)
House near Patapsco River 2700 square feet
Pasadena, MD
8% off
Price is AU$9,269
AU$9,269
AU$1,324 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 AU$12,665
AU$12,665
AU$1,809 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 AU$3,092
AU$3,092
AU$442 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
(11 reviews)
Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
Pasadena, MD
8% off
Price is AU$9,243
AU$9,243
AU$1,320 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
1010 out of 10 rating
Exceptional
(95 reviews)
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Royal Oak, MD
8% off
Price is AU$5,627
AU$5,627
AU$804 per night
includes taxes & fees
Image gallery for Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
1010 out of 10 rating
Exceptional
(5 reviews)
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
Annapolis, MD
12% off
Price is AU$10,586
AU$10,586
AU$1,512 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 AU$9,182
AU$9,182
AU$1,312 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 AU$6,634
AU$6,634
AU$948 per night
includes taxes & fees
Image gallery for Pasadena, MD close to Annapolis/WDC/Baltimore
1010 out of 10 rating
Exceptional
(35 reviews)
Pasadena, MD close to Annapolis/WDC/Baltimore
Pasadena, MD
11% off
Price is AU$3,532
AU$3,532
AU$505 per night
includes taxes & fees
Image gallery for St Michaels Retreat, Log Cabin, Family & Pet-Friendly
9.89.8 out of 10 rating
Exceptional
(6 reviews)
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
St. Michaels, MD
16% off
Price is AU$9,505
AU$9,505
AU$1,358 per night
includes taxes & fees
Image gallery for Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
1010 out of 10 rating
Exceptional
(6 reviews)
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Centreville, MD
9% off
Price is AU$13,804
AU$13,804
AU$1,972 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 AU$4,491
AU$4,491
AU$642 per night
includes taxes & fees
Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
1010 out of 10 rating
Exceptional
(15 reviews)
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall, MD
17% off
Price is AU$2,811
AU$2,811
AU$402 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
(93 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is AU$5,511
AU$5,511
AU$787 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
(5 reviews)
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side, MD
8% off
Price is AU$14,195
AU$14,195
AU$2,028 per night
includes taxes & fees
Image gallery for Cozy, unique, historic registered cottage on the Corsica River!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy, unique, historic registered cottage on the Corsica River!
Centreville, MD
8% off
Price is AU$2,702
AU$2,702
AU$386 per night
includes taxes & fees
Image gallery for Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.49.4 out of 10 rating
Exceptional
(87 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena, MD
8% off
Price is AU$5,875
AU$5,875
AU$839 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
8% off
Price is AU$7,458
AU$7,458
AU$1,065 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 AU$11,497
AU$11,497
AU$1,642 per night
includes taxes & fees
Image gallery for Charming 239-year-old former tavern 1 block to water & shops
1010 out of 10 rating
Exceptional
(9 reviews)
Charming 239-year-old former tavern 1 block to water & shops
Annapolis, MD
8% off
Price is AU$9,184
AU$9,184
AU$1,312 per night
includes taxes & fees
Image gallery for Gem in Downtown Annapolis, close to USNA, St. John's College
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Gem in Downtown Annapolis, close to USNA, St. John's College
Annapolis, MD
8% off
Price is AU$5,085
AU$5,085
AU$726 per night
includes taxes & fees
Image gallery for Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
1010 out of 10 rating
Exceptional
(139 reviews)
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Sherwood, MD
10% off
Price is AU$3,793
AU$3,793
AU$542 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
(35 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Annapolis, MD
8% off
Price is AU$2,442
AU$2,442
AU$349 per night
includes taxes & fees
Find spaces that suit your style
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Top rated rentals - Chesapeake Exploration Center
Fun times in Annapolis
1010 out of 10
Exceptionalexceptional
157 reviews(157 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