The Best Hotels Closest to Annapolis Sailing School in Annapolis for 2026

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Our top choices for Annapolis Sailing School hotels

1. 86 State Circle - Luxury Boutique Hotel

Historic District, 2 km from Annapolis Sailing School

Jo

AED 1,590 total

includes taxes & fees

2 Aug - 3 Aug

2. 134 Prince - Luxury Boutique Hotel

1.6 km from Annapolis Sailing School

Chris

AED 893 total

includes taxes & fees

4 Aug - 5 Aug

3. Graduate by Hilton Annapolis

2.3 km from Annapolis Sailing School

Gabriela

AED 649 total

includes taxes & fees

16 Aug - 17 Aug

4. Flag House Inn

Historic District, 1.7 km from Annapolis Sailing School

Tyler

AED 951 total

includes taxes & fees

2 Aug - 3 Aug

5. Historic Inns of Annapolis

Historic District, 1.9 km from Annapolis Sailing School

Monica

AED 569 total

includes taxes & fees

12 Aug - 13 Aug

6. Residence Inn By Marriott Annapolis

3 km from Annapolis Sailing School

Caitlin

AED 636 total

includes taxes & fees

3 Aug - 4 Aug

Premium bedding, down comforters, pillowtop beds, in-room safe

7. Annapolis Waterfront Hotel, Autograph Collection

Historic District, 1.4 km from Annapolis Sailing School

Salvatore

AED 830 total

includes taxes & fees

23 Aug - 24 Aug

8. The Westin Annapolis

2.7 km from Annapolis Sailing School

Jessica

AED 708 total

includes taxes & fees

2 Aug - 3 Aug

9. Fairfield Inn & Suites By Marriott Annapolis

3 km from Annapolis Sailing School

Eileen

AED 565 total

includes taxes & fees

3 Aug - 4 Aug

10. Hilton Garden Inn Annapolis Downtown

2.5 km from Annapolis Sailing School

Ava

AED 450 total

includes taxes & fees

16 Aug - 17 Aug

11. The Inn at Chesapeake Bay Beach Club

13 km from Annapolis Sailing School

Jamie

AED 1,054 total

includes taxes & fees

3 Aug - 4 Aug

12. SpringHill Suites by Marriott Annapolis

6.4 km from Annapolis Sailing School

Thomas

AED 498 total

includes taxes & fees

23 Aug - 24 Aug

13. TownePlace Suites by Marriott Annapolis

6.7 km from Annapolis Sailing School

Jamila

AED 461 total

includes taxes & fees

5 Aug - 6 Aug

14. Country Inn & Suites by Radisson, Annapolis, MD

7.4 km from Annapolis Sailing School

Jing

AED 399 total

includes taxes & fees

23 Aug - 24 Aug

15. Microtel Inn & Suites by Wyndham Gambrills

19.7 km from Annapolis Sailing School

Patrick

AED 402 total

includes taxes & fees

30 Aug - 31 Aug

16. Candlewood Suites Annapolis by IHG

6.2 km from Annapolis Sailing School

Javier

AED 397 total

includes taxes & fees

16 Aug - 17 Aug

17. Crowne Plaza Annapolis by IHG

6.3 km from Annapolis Sailing School

Douglas and Lori

AED 492 total

includes taxes & fees

16 Aug - 17 Aug

18. DoubleTree by Hilton Hotel Annapolis

6.3 km from Annapolis Sailing School

Lena

AED 409 total

includes taxes & fees

30 Aug - 31 Aug

19. Sonesta ES Suites Annapolis

6.6 km from Annapolis Sailing School

Daniela

AED 427 total

includes taxes & fees

30 Aug - 31 Aug

20. Courtyard by Marriott Annapolis

6.8 km from Annapolis Sailing School

Margaret

AED 440 total

includes taxes & fees

30 Aug - 31 Aug

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Compare popular hotels close to Annapolis Sailing School

Property	Property class	Guest rating
86 State Circle - Luxury Boutique Hotel	2.0 star property	10.0 Exceptional 8 reviews	View
134 Prince - Luxury Boutique Hotel	2.5 star property	9.8 Exceptional 41 reviews	View
Graduate by Hilton Annapolis	4.0 star property	9.4 Exceptional 1,008 reviews	View
Flag House Inn	3.5 star property	9.2 Wonderful 95 reviews	View
Historic Inns of Annapolis	3.5 star property	9.0 Wonderful 1,899 reviews	View

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"The decorations were definitely unique. Loved the location. Parking extremely convenient. All great!! Highly recommend."

Bay View Studio Apartment

10/10 Excellent

"We really enjoyed staying at this property. The house was so clean, roomy, comfortable and had everything we needed. We loved sitting on the deck and watching the water. And when it rained, we just moved to the covered porch. The neighborhood was beautiful and quiet. We were close to old town Annapolis for lots of fun and dining options. Checking in was so easy. Directions for getting to the location, into the house, and where to park were so easy to follow. We hope to be back for another visit. Thank you"

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

10/10 Excellent

"My girlfriends and I take a long trip every year to a different city. We are at a point in our lives where we have very high standards and this beautiful home met all of our needs and more! It is in a quiet Eastport neighborhood, with approximately 8 to 10 minute walk to the heart of Annapolis. We each had our own bedroom and there were three full bathrooms (each with a bidet!!) and an outdoor shower. The living space was beautifully decorated and very spacious. The kitchen was updated and was a lovely space to create our happy hour snacks and our morning meals. The outdoor deck and patio with fire pit were fantastic for our late night wine talks! Because we go out for dinner every night, we didn't use the dining room but for people who want to cook and eat in, it is the perfect space! They even had a music room with piano and a guitar for the musically inclined. The entire house was super clean! There is a driveway right beside the home. We parked our car and unpacked and didn't start it until we left. The location is extremely walkable to everything. We had a minor issue on the first night with one of the toilets, and the host responded super fast. The handyman fixed the problem and was super sweet as well. The experience we had with this rental was incredible, and we would definitely stay here again on a future trip to Annapolis. Highly recommend!!!"

Luxury Home w Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

10/10 Excellent

"This property was truly a wonderful place to stay! It is beautiful, well-kept with great amenities (jacuzzi tub, barbecue pit, private driveway, etc.), and we were very cozy and comfortable. The view of the Chesapeake Bay from the primary bedroom is breathtaking! Also, the location in Eastport with its great restaurants which is within walking distance to Annapolis and the US Naval Academy is very convenient. We highly recommend staying at this property for a wonderful get away!"

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

10/10 Excellent

"I stayed at Below Deck for 2 weeks and had an amazing time staying at this home. I work from home so I spent the weekdays working and then would explore the town and waterways every day after work - so much to do in Annapolis in the summer, especially for water sport lovers! The backyard and deck setup was so nice for grilling and hanging out with my dogs. The bed was comfortable. The kitchen was stocked with everything you’d need. I’ll definitely be returning!"

Other attractions near Annapolis Sailing School

A marina with boats docked, wooden pilings, and a clear sky.

Susan Campbell Park

Susan Campbell Park is just one of the places to see in Annapolis, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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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, check out the 91 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Annapolis Sailing School?

Annapolis Waterfront Hotel, Autograph Collection is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and a 24-hour fitness center. It's located just a short 0.8 mi (1.4 km) from Annapolis Sailing School. Other good choices within 5 miles include Historic Inns of Annapolis and Inn at Horn Point.

How many hotels are there near Annapolis Sailing School?

Expedia has 91 hotels and other accommodations 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, most room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals near Annapolis Sailing School.

Where can I learn more about changing or cancelling my trip in the area near Annapolis Sailing School?

To access more information about picking new dates or cancelling your stay near Annapolis Sailing School, go to https://www.expedia.com/service/.

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, Kunta Kinte Plaque & Alex Haley Memorial, and Maynard-Burgess House. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.

Find hotels near Annapolis Sailing School, Annapolis from AED 397

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Our top choices for Annapolis Sailing School hotels

1. 86 State Circle - Luxury Boutique Hotel

2. 134 Prince - Luxury Boutique Hotel

3. Graduate by Hilton Annapolis

4. Flag House Inn

5. Historic Inns of Annapolis

6. Residence Inn By Marriott Annapolis

7. Annapolis Waterfront Hotel, Autograph Collection

8. The Westin Annapolis

9. Fairfield Inn & Suites By Marriott Annapolis

10. Hilton Garden Inn Annapolis Downtown

11. The Inn at Chesapeake Bay Beach Club

12. SpringHill Suites by Marriott Annapolis

13. TownePlace Suites by Marriott Annapolis

14. Country Inn & Suites by Radisson, Annapolis, MD

15. Microtel Inn & Suites by Wyndham Gambrills

16. Candlewood Suites Annapolis by IHG

17. Crowne Plaza Annapolis by IHG

18. DoubleTree by Hilton Hotel Annapolis

19. Sonesta ES Suites Annapolis

20. Courtyard by Marriott Annapolis

Compare popular hotels close to Annapolis Sailing School

Top Annapolis Sailing School Hotel Reviews

Graduate by Hilton Annapolis

Other attractions near Annapolis Sailing School

Susan Campbell Park

Frequently asked questions