
Holiday rentals near Annapolis Harbour Center
We found 1,071 holiday rentals — enter your dates for availability
If you are looking to stay near Annapolis Harbour Center, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, which might include parking and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Annapolis Harbour Center
Showing deals for:3 Oct - 10 Oct
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 NZ$39,830
NZ$39,830
NZ$5,690 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 NZ$9,649
NZ$9,649
NZ$1,378 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 NZ$11,223
NZ$11,223
NZ$1,603 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 NZ$3,931
NZ$3,931
NZ$562 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 NZ$13,776
NZ$13,776
NZ$1,968 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 NZ$12,632
NZ$12,632
NZ$1,805 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 NZ$5,271
NZ$5,271
NZ$753 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 NZ$2,327
NZ$2,327
NZ$332 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 NZ$9,350
NZ$9,350
NZ$1,336 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 NZ$2,665
NZ$2,665
NZ$381 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 NZ$1,923
NZ$1,923
NZ$275 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 NZ$6,500
NZ$6,500
NZ$929 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 NZ$9,025
NZ$9,025
NZ$1,289 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 NZ$14,631
NZ$14,631
NZ$2,090 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!

9.89.8 out of 10 rating
Exceptional
(17 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis, MD
16% off
Price is NZ$12,446
NZ$12,446
NZ$1,778 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,223
NZ$11,223
NZ$1,603 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway

9.89.8 out of 10 rating
Exceptional
(113 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman, MD
8% off
Price is NZ$3,121
NZ$3,121
NZ$446 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis

1010 out of 10 rating
Exceptional
(44 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
11% off
Price is NZ$7,481
NZ$7,481
NZ$1,069 per night
includes taxes & fees
Image gallery for The Santi Paradise

1010 out of 10 rating
Exceptional
(13 reviews)
The Santi Paradise
Glen Burnie, MD
8% off
Price is NZ$9,227
NZ$9,227
NZ$1,318 per night
includes taxes & fees
Image gallery for Waterfront Paradise on the Eastern Shore of Chesapeake Bay

1010 out of 10 rating
Exceptional
(64 reviews)
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Rock Hall, MD
8% off
Price is NZ$11,278
NZ$11,278
NZ$1,611 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 NZ$9,923
NZ$9,923
NZ$1,418 per night
includes taxes & fees
Image gallery for Blocks to the Boardwalk!

9.89.8 out of 10 rating
Exceptional
(38 reviews)
Blocks to the Boardwalk!
North Beach, MD
9% off
Price is NZ$2,007
NZ$2,007
NZ$287 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,114
NZ$6,114
NZ$873 per night
includes taxes & fees
Image gallery for Spacious Private Basement

1010 out of 10 rating
Exceptional
(6 reviews)
Spacious Private Basement
Severn, MD
7% off
Price is NZ$1,354
NZ$1,354
NZ$193 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Annapolis Harbour Center
Spacious Waterfront home with stunning views, pool, pier & parking mins to Annapolis
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Waterfront home with private pier mins to Annapolis
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Charming 3 Bedroom 3 Bath Beach Front Property
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
Zen Sunset Retreat on Waterfront at West River, MD
Sleeps 10 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Sunset Cove - peaceful 3-bedroom waterfront retreat in Arnold, MD
Sleeps 9 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Waterfront Home with Private Pier and Easy Access to USNA, Baltimore and DC
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
- 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