Holiday rentals near Annapolis Landing Marina
We found 1,140 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals near Annapolis Landing Marina that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Annapolis Landing Marina
Showing deals for:3 Oct - 10 Oct
Image gallery for Secluded Waterfront Property on 3 acres with swimming pool and dock.
1010 out of 10 rating
Exceptional
(47 reviews)
Secluded Waterfront Property on 3 acres with swimming pool and dock.
Bozman, MD
5% off
Price is AU$9,264
AU$9,264
AU$1,323 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$8,939
AU$8,939
AU$1,277 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
(33 reviews)
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Crownsville, MD
8% off
Price is AU$34,893
AU$34,893
AU$4,985 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$9,952
AU$9,952
AU$1,422 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
(20 reviews)
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side, MD
33% off
Price is AU$3,647
AU$3,647
AU$521 per night
includes taxes & fees
Image gallery for Studio in Downtown – Walk to Everything!
1010 out of 10 rating
Exceptional
(19 reviews)
Studio in Downtown – Walk to Everything!
St. Michaels, Maryland
12% off
Price is AU$3,038
AU$3,038
AU$434 per night
includes taxes & fees
Image gallery for The heart of St Michaels awaits.
1010 out of 10 rating
Exceptional
(39 reviews)
The heart of St Michaels awaits.
St. Michaels, Maryland
7% off
Price is AU$3,123
AU$3,123
AU$446 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$12,329
AU$12,329
AU$1,761 per night
includes taxes & fees
Image gallery for Gorgeous Creek Side Ranch-Style Estate With Dock
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Gorgeous Creek Side Ranch-Style Estate With Dock
Queenstown, Maryland
7% off
Price is AU$7,322
AU$7,322
AU$1,046 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(28 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is AU$11,291
AU$11,291
AU$1,613 per night
includes taxes & fees
Image gallery for Waterfront Sunset Bayview: sleeps 6
1010 out of 10 rating
Exceptional
(17 reviews)
Waterfront Sunset Bayview: sleeps 6
Chester, MD
8% off
Price is AU$4,851
AU$4,851
AU$693 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 101
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Guest Quarters at the Inn - 101
North Beach, MD
8% off
Price is AU$2,163
AU$2,163
AU$309 per night
includes taxes & fees
Image gallery for Pet-Friendly Cottage – Ideal for Summer Getaways!
1010 out of 10 rating
Exceptional
(6 reviews)
Pet-Friendly Cottage – Ideal for Summer Getaways!
Tilghman, Maryland
11% off
Price is AU$3,771
AU$3,771
AU$539 per night
includes taxes & fees
Image gallery for Dollhouse in Central Historic St Michaels
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Dollhouse in Central Historic St Michaels
St. Michaels, MD
12% off
Price is AU$3,200
AU$3,200
AU$457 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex
1010 out of 10 rating
Exceptional
(88 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is AU$8,657
AU$8,657
AU$1,237 per night
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 AU$2,476
AU$2,476
AU$354 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$1,799
AU$1,799
AU$257 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$5,993
AU$5,993
AU$856 per night
includes taxes & fees
Image gallery for Charming Waterfront Cottage Retreat near St. Michaels
1010 out of 10 rating
Exceptional
(6 reviews)
Charming Waterfront Cottage Retreat near St. Michaels
Bozman, MD
16% off
Price is AU$4,280
AU$4,280
AU$611 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
(45 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is AU$2,750
AU$2,750
AU$393 per night
includes taxes & fees
Image gallery for Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.69.6 out of 10 rating
Exceptional
(119 reviews)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
St. Michaels, MD
8% off
Price is AU$3,701
AU$3,701
AU$529 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
(113 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is AU$2,651
AU$2,651
AU$379 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
(6 reviews)
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side, MD
8% off
Price is AU$12,873
AU$12,873
AU$1,839 per night
includes taxes & fees
Image gallery for Kent Island Luxury Waterfront
1010 out of 10 rating
Exceptional
(6 reviews)
Kent Island Luxury Waterfront
Stevensville, MD
17% off
Price is AU$8,359
AU$8,359
AU$1,194 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Annapolis Landing Marina
Showing deals for: 1 Oct - 4 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
Sleeps 11 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The current price is AU$2,213
AU$2,213
for 3 nights, 1 home
AU$738 per night
includes taxes & fees
Holly Hill Haven Summ
Sleeps 10 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is AU$4,303
AU$4,303
for 3 nights, 1 home
AU$1,434 per night
includes taxes & fees
Stunning Waterfront Cottage with Breathtaking Views!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
210 reviews(210 reviews)
The current price is AU$2,465
AU$2,465
for 3 nights, 1 home
AU$822 per night
includes taxes & fees
Pet-Friendly & Spacious Home in Annapolis
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
The current price is AU$4,529
AU$4,529
for 3 nights, 1 home
AU$1,510 per night
includes taxes & fees
Waterfront Getaway, Dock Your Boat & Play!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$2,463
AU$2,463
for 3 nights, 1 home
AU$821 per night
includes taxes & fees
Charming Cottage with Hot Tub 1 Block from the Bay
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is AU$5,191
AU$5,191
for 3 nights, 1 home
AU$1,730 per night
includes taxes & fees
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