Holiday rentals near Annapolis Bowl
We found 1,080 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:14 Nov - 21 Nov
Image gallery for Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
1010 out of 10 rating
Exceptional
(10 reviews)
Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
North Beach, MD
16% off
Price is NZ$7,035
NZ$7,035
NZ$1,005 nightly
Includes taxes & fees
Image gallery for Edgewater/Mayo Gateaway w/ Hot Tub
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater, MD
7% off
Price is NZ$6,509
NZ$6,509
NZ$930 nightly
Includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is NZ$3,596
NZ$3,596
NZ$514 nightly
Includes taxes & fees
Image gallery for NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.89.8 out of 10 rating
Exceptional
(29 reviews)
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Annapolis, MD
12% off
Price is NZ$5,318
NZ$5,318
NZ$760 nightly
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$11,299
NZ$11,299
NZ$1,614 nightly
Includes taxes & fees
Image gallery for Waterfront Annapolis w/swimming pool & pier -July 20-26 available
1010 out of 10 rating
Exceptional
(47 reviews)
Waterfront Annapolis w/swimming pool & pier -July 20-26 available
Annapolis, MD
14% off
Price is NZ$5,546
NZ$5,546
NZ$792 nightly
Includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(30 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,221
NZ$12,221
NZ$1,746 nightly
Includes taxes & fees
Image gallery for Circa 1700 Chesapeake Colonial home on the National Register.
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville, MD
8% off
Price is NZ$6,639
NZ$6,639
NZ$948 nightly
Includes taxes & fees
Image gallery for Annapolis Entertainment Complex
1010 out of 10 rating
Exceptional
(90 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is NZ$9,035
NZ$9,035
NZ$1,291 nightly
Includes taxes & fees
Image gallery for Private Waterfront Home w/ Pier and 2+ Acres!
1010 out of 10 rating
Exceptional
(85 reviews)
Private Waterfront Home w/ Pier and 2+ Acres!
Deale, MD
7% off
Price is NZ$6,268
NZ$6,268
NZ$895 nightly
Includes taxes & fees
Image gallery for Peaceful getaway convenient to local amenities including beach, boating & food
9.89.8 out of 10 rating
Exceptional
(116 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is NZ$2,921
NZ$2,921
NZ$417 nightly
Includes taxes & fees
Image gallery for Eastern Shore beach cottage get-away
1010 out of 10 rating
Exceptional
(136 reviews)
Eastern Shore beach cottage get-away
Rock Hall, MD
8% off
Price is NZ$3,963
NZ$3,963
NZ$566 nightly
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$2,731
NZ$2,731
NZ$390 nightly
Includes taxes & fees
Image gallery for Island Life! Kent Island Waterfront with Pool-Bring your boat!
1010 out of 10 rating
Exceptional
(195 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville, MD
12% off
Price is NZ$5,548
NZ$5,548
NZ$793 nightly
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
(95 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is NZ$5,926
NZ$5,926
NZ$847 nightly
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
18% off
Price is NZ$4,479
NZ$4,479
NZ$640 nightly
Includes taxes & fees
Image gallery for Waterfront River Cottage for 2, dog-friendly
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Waterfront River Cottage for 2, dog-friendly
Severna Park, MD
6% off
Price is NZ$4,286
NZ$4,286
NZ$612 nightly
Includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$10,205
NZ$10,205
NZ$1,458 nightly
Includes taxes & fees
Image gallery for Welcome to our newly built house
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Welcome to our newly built house
Glen Burnie, MD
8% off
Price is NZ$4,957
NZ$4,957
NZ$708 nightly
Includes taxes & fees
Image gallery for Newly Updated EV Charger Ready Peaceful Home in Annapolis
8.88.8 out of 10 rating
Excellent
(5 reviews)
Newly Updated EV Charger Ready Peaceful Home in Annapolis
Annapolis, MD
12% off
Price is NZ$3,029
NZ$3,029
NZ$433 nightly
Includes taxes & fees
Image gallery for Modern Bay Dream
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Modern Bay Dream
Deale, MD
7% off
Price is NZ$6,607
NZ$6,607
NZ$944 nightly
Includes taxes & fees
Image gallery for Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
1010 out of 10 rating
Exceptional
(22 reviews)
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Severna Park, MD
7% off
Price is NZ$5,310
NZ$5,310
NZ$759 nightly
Includes taxes & fees
Image gallery for Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena, MD
8% off
Price is NZ$5,889
NZ$5,889
NZ$841 nightly
Includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10 rating
Exceptional
(236 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis, MD
8% off
Price is NZ$2,012
NZ$2,012
NZ$287 nightly
Includes taxes & fees
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Find the best place to stay - Annapolis Bowl
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
195 reviews(195 reviews)
Waterfront Getaway, Dock Your Boat & Play!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Sleeps 16 · 6 bedrooms · 4+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Floating 2 bed 2 bath condo stunning views of the bay
Sleeps 8 · 2 bedrooms · 2 bathrooms
6.86.8 out of 10
5 reviews(5 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