Holiday rentals near Annapolis Bowl
We found 1,062 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:19 Sept - 26 Sept
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$9,242
AU$9,242
AU$1,320 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$12,629
AU$12,629
AU$1,804 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$8,766
AU$8,766
AU$1,252 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$6,615
AU$6,615
AU$945 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$10,556
AU$10,556
AU$1,508 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$9,156
AU$9,156
AU$1,308 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$3,522
AU$3,522
AU$503 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$14,154
AU$14,154
AU$2,022 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$7,437
AU$7,437
AU$1,062 per night
includes taxes & fees
Image gallery for Modern Bay Dream
1010 out of 10 rating
Exceptional
(15 reviews)
Modern Bay Dream
Deale, MD
8% off
Price is AU$5,916
AU$5,916
AU$845 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$5,495
AU$5,495
AU$785 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$11,464
AU$11,464
AU$1,638 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$5,858
AU$5,858
AU$837 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10 rating
Exceptional
(15 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis, MD
11% off
Price is AU$3,123
AU$3,123
AU$446 per night
includes taxes & fees
Image gallery for Beautiful Historic Home With Great Location!
1010 out of 10 rating
Exceptional
(124 reviews)
Beautiful Historic Home With Great Location!
Annapolis, MD
7% off
Price is AU$5,853
AU$5,853
AU$836 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$9,158
AU$9,158
AU$1,308 per night
includes taxes & fees
Image gallery for BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
1010 out of 10 rating
Exceptional
(17 reviews)
BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
Millersville, MD
16% off
Price is AU$3,851
AU$3,851
AU$550 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$5,071
AU$5,071
AU$724 per night
includes taxes & fees
Image gallery for Grandma's Summer House @ Beverly Beach
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Grandma's Summer House @ Beverly Beach
Edgewater, MD
7% off
Price is AU$3,661
AU$3,661
AU$523 per night
includes taxes & fees
Image gallery for House w/Water Views of Rock Creek 2BA 2BA Cottage
1010 out of 10 rating
Exceptional
(27 reviews)
House w/Water Views of Rock Creek 2BA 2BA Cottage
Pasadena, MD
7% off
Price is AU$2,279
AU$2,279
AU$326 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$2,435
AU$2,435
AU$348 per night
includes taxes & fees
Image gallery for Truly Waterfront Cottage
1010 out of 10 rating
Exceptional
(74 reviews)
Truly Waterfront Cottage
Pasadena, MD
8% off
Price is AU$2,665
AU$2,665
AU$381 per night
includes taxes & fees
Image gallery for Enchanting West River Retreat
1010 out of 10 rating
Exceptional
(8 reviews)
Enchanting West River Retreat
West River, MD
7% off
Price is AU$5,084
AU$5,084
AU$726 per night
includes taxes & fees
Image gallery for Sunset Lodge on the Bay
1010 out of 10 rating
Exceptional
(41 reviews)
Sunset Lodge on the Bay
Rock Hall, MD
13% off
Price is AU$11,873
AU$11,873
AU$1,696 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Annapolis Bowl
Showing deals for: 13 Sept - 16 Sept
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Sleeps 11 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
209 reviews(209 reviews)
The current price is AU$2,113
AU$2,113
for 3 nights, 1 cottage
AU$704 per night
includes taxes & fees
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Sleeps 16 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
The current price is AU$6,941
AU$6,941
for 3 nights, 1 home
AU$2,314 per night
includes taxes & fees
Chesapeake Houseboat Getaway on Kent Island, Maryland
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
The current price is AU$1,774
AU$1,774
for 3 nights, 1 houseboat
AU$591 per night
includes taxes & fees
Stunning Waterfront Cottage with Breathtaking Views!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
208 reviews(208 reviews)
The current price is AU$2,502
AU$2,502
for 3 nights, 1 home
AU$834 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Sleeps 14 · 5 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
The current price is AU$3,039
AU$3,039
for 3 nights, 1 home
AU$1,013 per night
includes taxes & fees
Edgewater/Mayo Getaway!
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
The current price is AU$2,077
AU$2,077
for 3 nights, 1 home
AU$692 per night
includes taxes & fees
Top rated rentals - Annapolis Bowl
Great place for a family reunion
1010 out of 10
Exceptionalexceptional
186 reviews(186 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