Holiday rentals near Annapolis Bowl
We found 1,075 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:7 Nov - 14 Nov
Image gallery for Brand New Spacious Luxury Home
1010 out of 10 rating
Exceptional
(8 reviews)
Brand New Spacious Luxury Home
Annapolis, MD
7% off
Price is S$8,624
S$8,624
S$1,232 per night
includes taxes & fees
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 S$5,285
S$5,285
S$755 per night
includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is S$2,741
S$2,741
S$392 per night
includes taxes & fees
Image gallery for Edgewater/Mayo Gateaway w/ Hot Tub
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater, MD
7% off
Price is S$4,594
S$4,594
S$656 per night
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 S$4,077
S$4,077
S$582 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
(52 reviews)
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Arnold, MD
12% off
Price is S$7,602
S$7,602
S$1,086 per night
includes taxes & fees
Image gallery for Waterfront Annapolis w/swimming pool & pier -July 20-26 available
1010 out of 10 rating
Exceptional
(46 reviews)
Waterfront Annapolis w/swimming pool & pier -July 20-26 available
Annapolis, MD
14% off
Price is S$4,251
S$4,251
S$607 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 S$2,955
S$2,955
S$422 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 S$8,831
S$8,831
S$1,262 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 S$3,787
S$3,787
S$541 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 S$3,780
S$3,780
S$540 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
(115 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is S$2,227
S$2,227
S$318 per night
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 S$6,855
S$6,855
S$979 per night
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 S$3,020
S$3,020
S$431 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 S$5,099
S$5,099
S$728 per night
includes taxes & fees
Image gallery for Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall, MD
8% off
Price is S$12,901
S$12,901
S$1,843 per night
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 S$4,511
S$4,511
S$644 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
(95 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is S$4,562
S$4,562
S$652 per night
includes taxes & fees
Image gallery for Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Deale, MD
8% off
Price is S$2,406
S$2,406
S$344 per night
includes taxes & fees
Image gallery for Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
1010 out of 10 rating
Exceptional
(11 reviews)
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Stevensville, MD
16% off
Price is S$4,570
S$4,570
S$653 per night
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 S$4,070
S$4,070
S$581 per night
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 S$1,542
S$1,542
S$220 per night
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
8% off
Price is S$4,707
S$4,707
S$672 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
(48 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is S$2,308
S$2,308
S$330 per night
includes taxes & fees
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Find the best place to stay - Annapolis Bowl
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
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)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Waterfront Getaway, Dock Your Boat & Play!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 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)
Circa 1700 Chesapeake Colonial home on the National Register.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
53 reviews(53 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