Holiday rentals near Annapolis Bowl
We found 1,106 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Annapolis Bowl that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Annapolis Bowl
Showing deals for:3 July - 10 July
Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
8.08.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
Annapolis
16% off
Price is AU$12,826
AU$12,826
for 7 nights, 1 home
AU$1,832 per night
includes taxes & fees
Image gallery for Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Annapolis
12% off
Price is AU$7,134
AU$7,134
for 7 nights, 1 home
AU$1,019 per night
includes taxes & fees
Image gallery for Brand New Spacious Luxury Home
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Brand New Spacious Luxury Home
Annapolis
8% off
Price is AU$11,465
AU$11,465
for 7 nights, 1 home
AU$1,638 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.69.6 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis
8% off
Price is AU$6,173
AU$6,173
for 7 nights, 1 home
AU$882 per night
includes taxes & fees
Image gallery for Lower Level Loft - Adorable Studio Apt. Near BWI
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Lower Level Loft - Adorable Studio Apt. Near BWI
Millersville
8% off
Price is AU$790
AU$790
for 7 nights, 1 home
AU$113 per night
includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis
12% off
Price is AU$9,081
AU$9,081
for 7 nights, 1 home
AU$1,297 per night
includes taxes & fees
Image gallery for Mins to Annap; Luxury Townhome
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Mins to Annap; Luxury Townhome
Arnold
8% off
Price is AU$6,260
AU$6,260
for 7 nights, 1 home
AU$894 per night
includes taxes & fees
Image gallery for Charming 3BDR Bungalow Near Annapolis
9.69.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Charming 3BDR Bungalow Near Annapolis
Riva
9% off
Price is AU$3,314
AU$3,314
for 7 nights, 1 home
AU$473 per night
includes taxes & fees
Image gallery for Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.49.4 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena
8% off
Price is AU$5,546
AU$5,546
for 7 nights, 1 home
AU$792 per night
includes taxes & fees
Image gallery for Charming Annapolis Victorian
1010 out of 10, Exceptional, (73 reviews)
Exceptional
(73 reviews)
Charming Annapolis Victorian
Annapolis
8% off
Price is AU$8,904
AU$8,904
for 7 nights, 1 home
AU$1,272 per night
includes taxes & fees
Image gallery for Historic Annapolis Charmer <1Mile to NMC Stadium
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Historic Annapolis Charmer <1Mile to NMC Stadium
Annapolis
16% off
Price is AU$14,003
AU$14,003
for 7 nights, 1 home
AU$2,000 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
7% off
Price is AU$2,557
AU$2,557
for 7 nights, 1 apartment
AU$365 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis
12% off
Price is AU$3,412
AU$3,412
for 7 nights, 1 room
AU$487 per night
includes taxes & fees
Image gallery for The Liberty House- Pristine Renovation with parking
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
The Liberty House- Pristine Renovation with parking
Annapolis
8% off
Price is AU$6,015
AU$6,015
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Image gallery for Brand New Cottage Steps from the Beach!
1010 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Brand New Cottage Steps from the Beach!
Rock Hall
8% off
Price is AU$2,817
AU$2,817
for 7 nights, 1 home
AU$402 per night
includes taxes & fees
Image gallery for Cute waterfront apartment -- 8 min from the beach!
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Cute waterfront apartment -- 8 min from the beach!
Rock Hall
8% off
Price is AU$2,502
AU$2,502
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Image gallery for 50 Shades of Blue -McHenry Row
8.08.0 out of 10, Very good, (6 reviews)
Very good
(6 reviews)
50 Shades of Blue -McHenry Row
Baltimore
12% off
Price is AU$2,422
AU$2,422
for 7 nights, 1 home
AU$346 per night
includes taxes & fees
Image gallery for Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Riva
21% off
Price is AU$4,188
AU$4,188
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10, Exceptional, (247 reviews)
Exceptional
(247 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis
8% off
Price is AU$1,770
AU$1,770
for 7 nights, 1 cottage
AU$253 per night
includes taxes & fees
Image gallery for Cozy Cottage with Beach Access
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Cozy Cottage with Beach Access
Annapolis
7% off
Price is AU$4,345
AU$4,345
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
Image gallery for New Loft w/South River view from treehouse deck!
1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
New Loft w/South River view from treehouse deck!
Riva
15% off
Price is AU$1,428
AU$1,428
for 7 nights, 1 apartment
AU$204 per night
includes taxes & fees
Image gallery for Dog friendly! Next to Navy Stadium and DTA Shuttle!
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Annapolis
12% off
Price is AU$5,764
AU$5,764
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Image gallery for Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.89.8 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
8% off
Price is AU$9,536
AU$9,536
for 7 nights, 1 home
AU$1,362 per night
includes taxes & fees
Image gallery for 18th Cent. Charm in Historic Downtown Annapolis
9.09.0 out of 10, Wonderful, (14 reviews)
Wonderful
(14 reviews)
18th Cent. Charm in Historic Downtown Annapolis
Annapolis
16% off
Price is AU$2,866
AU$2,866
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
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Find the best place to stay - Annapolis Bowl
Charming Annapolis WaterVIEW Home
Sleeps 14 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
65 reviews
(65 reviews)
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
40 reviews
(40 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
206 reviews
(206 reviews)
Annapolis waterfront "tiny house" in garden setting
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
247 reviews
(247 reviews)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
1010 out of 10
43 reviews
(43 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
57 reviews
(57 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