Holiday rentals near U.S. Naval Academy
We found 676 holiday rentals — enter your dates for availability
Select the perfect holiday rental that's near U.S. Naval Academy. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - U.S. Naval Academy
Showing deals for:26 Sept - 3 Oct
Image gallery for Edgewater/Mayo Getaway!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Edgewater/Mayo Getaway!
Edgewater, MD
7% off
Price is AU$5,207
AU$5,207
AU$744 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
(32 reviews)
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Crownsville, MD
5% off
Price is AU$36,780
AU$36,780
AU$5,254 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$9,071
AU$9,071
AU$1,296 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 AU$10,099
AU$10,099
AU$1,443 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$12,511
AU$12,511
AU$1,787 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$11,458
AU$11,458
AU$1,637 per night
includes taxes & fees
Image gallery for Fisher House: Steps From USNA + Covered Parking!
1010 out of 10 rating
Exceptional
(10 reviews)
Fisher House: Steps From USNA + Covered Parking!
Annapolis, MD
8% off
Price is AU$10,719
AU$10,719
AU$1,531 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
8% off
Price is AU$5,519
AU$5,519
AU$788 per night
includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis, MD
12% off
Price is AU$9,257
AU$9,257
AU$1,322 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
(94 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is AU$5,412
AU$5,412
AU$773 per night
includes taxes & fees
Image gallery for New Loft w/South River view from treehouse deck!
1010 out of 10 rating
Exceptional
(21 reviews)
New Loft w/South River view from treehouse deck!
Riva, MD
15% off
Price is AU$1,826
AU$1,826
AU$261 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 AU$6,081
AU$6,081
AU$869 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is AU$10,099
AU$10,099
AU$1,443 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis, MD
16% off
Price is AU$11,224
AU$11,224
AU$1,603 per night
includes taxes & fees
Image gallery for Secluded Cozy Cottage in Historic Downtown
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Secluded Cozy Cottage in Historic Downtown
Annapolis, MD
22% off
Price is AU$5,961
AU$5,961
AU$852 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10 rating
Exceptional
(234 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis, MD
8% off
Price is AU$1,864
AU$1,864
AU$266 per night
includes taxes & fees
Image gallery for NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
1010 out of 10 rating
Exceptional
(6 reviews)
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Annapolis, MD
12% off
Price is AU$7,756
AU$7,756
AU$1,108 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis
1010 out of 10 rating
Exceptional
(44 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
11% off
Price is AU$6,228
AU$6,228
AU$890 per night
includes taxes & fees
Image gallery for Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Annapolis, MD
8% off
Price is AU$3,127
AU$3,127
AU$447 per night
includes taxes & fees
Image gallery for Waterfront Oasis of Annapolis Star
1010 out of 10 rating
Exceptional
(73 reviews)
Waterfront Oasis of Annapolis Star
Annapolis, MD
8% off
Price is AU$3,964
AU$3,964
AU$566 per night
includes taxes & fees
Image gallery for NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
9.89.8 out of 10 rating
Exceptional
(9 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Annapolis, MD
8% off
Price is AU$16,658
AU$16,658
AU$2,380 per night
includes taxes & fees
Image gallery for Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
1010 out of 10 rating
Exceptional
(21 reviews)
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Edgewater, MD
8% off
Price is AU$5,599
AU$5,599
AU$800 per night
includes taxes & fees
Image gallery for Wright's Cottage- Pet's Welcome & EV Charging
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Wright's Cottage- Pet's Welcome & EV Charging
Annapolis, Maryland
11% off
Price is AU$1,887
AU$1,887
AU$270 per night
includes taxes & fees
Image gallery for New! Stylish downtown home w/awesome outdoor area!
9.89.8 out of 10 rating
Exceptional
(23 reviews)
New! Stylish downtown home w/awesome outdoor area!
Stevensville, MD
8% off
Price is AU$4,153
AU$4,153
AU$593 per night
includes taxes & fees
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Find properties near top attractions in U.S. Naval Academy
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Find the best place to stay - U.S. Naval Academy
Modern Styled Home in Historic Annapolis Eastport Neighborhood
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Private Cottage on gated estate
Sleeps 5 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
223 reviews(223 reviews)
Timeless Charm Meets Modern Comfort
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
2 Mi to Sandy Point State Park: Home w/ Deck!
Sleeps 8 · 3 bedrooms · 2+ bathrooms
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Top rated rentals - U.S. Naval Academy
Lovely townhome in the heart of the historic district
1010 out of 10
Exceptionalexceptional
117 reviews(117 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