Top Hotels Near Annapolis Sailing School in Annapolis from NZ$146

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Our top choices for Annapolis Sailing School hotels

Flag House Inn

Flag House Inn
3.5 star property
Historic District, 1.7 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (84)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is NZ$357
includes taxes & fees
29 Dec - 30 Dec
Flag House Inn

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
2.3 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (1000)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is NZ$293
includes taxes & fees
4 Jan - 5 Jan 2026
Graduate by Hilton Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District, 1.9 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1897)
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (167)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is NZ$215
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites By Marriott Annapolis

Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3.0 star property
3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (57)
"had a great stay staff was fabulous room was perfect for our needs location was convenient to shopping and restaurants"
United States
karen c.
The price is NZ$248
includes taxes & fees
1 Jan - 2 Jan 2026
Residence Inn By Marriott Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District, 1.4 km from Annapolis Sailing School
8.8 out of 10, Excellent, (893)
"Great location, nice and clean "
United States
Micah
The price is NZ$430
includes taxes & fees
4 Jan - 5 Jan 2026
Annapolis Waterfront Hotel, Autograph Collection

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
2.5 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1003)
"Great value for stay with breakfast included "
United States
Aisling
The price is NZ$175
includes taxes & fees
11 Jan - 12 Jan 2026
Hilton Garden Inn Annapolis Downtown

The Westin Annapolis

The Westin Annapolis
4.0 star property
2.7 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1002)
"Beautiful and perfect location"
United States
Lauren
The price is NZ$272
includes taxes & fees
29 Dec - 30 Dec
The Westin Annapolis

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
1.6 km from Annapolis Sailing School
9.8 out of 10, Exceptional, (32)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District, 2 km from Annapolis Sailing School
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is NZ$546
includes taxes & fees
4 Jan - 5 Jan 2026
86 State Circle - Luxury Boutique Hotel

TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
6.6 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (52)
"The staff was welcoming, the room was very clean and comfortable and tue pocation waa great."
United States
Karen
The price is NZ$189
includes taxes & fees
4 Jan - 5 Jan 2026
TownePlace Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
6.4 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1001)
"Great location and friendly staff. "
United States
Shana
The price is NZ$214
includes taxes & fees
2 Jan - 3 Jan 2026
SpringHill Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
7.3 km from Annapolis Sailing School
9.0 out of 10, Wonderful, (1005)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is NZ$183
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
6.2 km from Annapolis Sailing School
8.8 out of 10, Excellent, (182)
"The staff was extremely pleasant and enjoyable to work with!! "
United States
Laura
The price is NZ$156
includes taxes & fees
25 Jan - 26 Jan 2026
Candlewood Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
6.3 km from Annapolis Sailing School
8.8 out of 10, Excellent, (1009)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is NZ$207
includes taxes & fees
25 Jan - 26 Jan 2026
Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
6.6 km from Annapolis Sailing School
8.8 out of 10, Excellent, (968)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is NZ$178
includes taxes & fees
15 Jan - 16 Jan 2026
Sonesta ES Suites Annapolis

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
13 km from Annapolis Sailing School
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is NZ$357
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Chesapeake Bay Beach Club

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
6.3 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1005)
"Great stay "
United States
Jose Miguel
The price is NZ$146
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
6.8 km from Annapolis Sailing School
8.6 out of 10, Excellent, (1000)
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is NZ$164
includes taxes & fees
12 Jan - 13 Jan 2026
Courtyard by Marriott Annapolis

Kent Island Resort

Kent Island Resort
3.5 star property
13.1 km from Annapolis Sailing School
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is NZ$304
includes taxes & fees
1 Jan - 2 Jan 2026
Kent Island Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Annapolis Sailing School Hotel Reviews

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Frequently asked questions

What's the area like around Annapolis Sailing School?
Annapolis Sailing School is located in an area of Annapolis known for its interesting historical sites. If you're looking for a convenient place to stay, take a look at the 98 hotels and other accommodation options you'll find within a mile.
What's the best place to stay near Annapolis Sailing School?
Annapolis Waterfront Hotel, Autograph Collection is one of the top choices for your stay based on our traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. It's located just a short 0.9 mi (1.4 km) from Annapolis Sailing School. Other good choices within 5 miles include Historic Inns of Annapolis and Graduate by Hilton Annapolis.
How many hotels will I be able to find near Annapolis Sailing School?
Expedia has 98 hotels and other accommodation options within a mile from Annapolis Sailing School.
If I need to cancel the hotel reservation for my stay near Annapolis Sailing School, will I receive a refund?
Yes, you'll find most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review the best options available near Annapolis Sailing School.
What can I see and do near Annapolis Sailing School?
Study the collections at Annapolis Maritime Museum, London Town or Hammond-Harwood House. Explore landmarks like William Paca House, 97, 99 and 101 East Street and Stanton School & Community Center. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.