Find hotels near Annapolis Sailing School, Annapolis from $85

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Our top choices for Annapolis Sailing School hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
1.5 mi from Annapolis Sailing School
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
$130 nightly
The price is $148
Dec 21 - Dec 22
Total with taxes and fees
Graduate by Hilton Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District, 1.2 mi from Annapolis Sailing School
9.0 out of 10, Wonderful, (1907)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
$164 nightly
The price is $187
Dec 17 - Dec 18
Total with taxes and fees
Historic Inns of Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
1.9 mi from Annapolis Sailing School
9.0 out of 10, Wonderful, (165)
"Beautiful and very modern, breakfast was great"
United States
Dominic
$110 nightly
The price is $125
Dec 15 - Dec 16
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis

Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3.0 star property
1.9 mi from Annapolis Sailing School
9.0 out of 10, Wonderful, (54)
"had a great stay staff was fabulous room was perfect for our needs location was convenient to shopping and restaurants"
United States
karen c.
$127 nightly
The price is $145
Dec 15 - Dec 16
Total with taxes and fees
Residence Inn By Marriott Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District, 0.9 mi from Annapolis Sailing School
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
$178 nightly
The price is $203
Dec 17 - Dec 18
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
1.5 mi from Annapolis Sailing School
8.6 out of 10, Excellent, (1006)
"Great value for stay with breakfast included "
United States
Aisling
$79 nightly
The price is $90
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown

The Westin Annapolis

The Westin Annapolis
4.0 star property
1.7 mi from Annapolis Sailing School
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
$154 nightly
The price is $176
Dec 14 - Dec 15
Total with taxes and fees
The Westin Annapolis

TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
4.1 mi from Annapolis Sailing School
9.4 out of 10, Exceptional, (48)
"Pet friendly."
United States
Sam
$93 nightly
The price is $106
Dec 29 - Dec 30
Total with taxes and fees
TownePlace Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
4 mi from Annapolis Sailing School
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
$93 nightly
The price is $106
Dec 18 - Dec 19
Total with taxes and fees
SpringHill Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
4.5 mi from Annapolis Sailing School
9.0 out of 10, Wonderful, (1001)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
$87 nightly
The price is $99
Jan 1 - Jan 2, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
3.8 mi from Annapolis Sailing School
8.8 out of 10, Excellent, (179)
"Nice staff, clean room, comfortable bed. "
United States
Jayne
$84 nightly
The price is $96
Dec 19 - Dec 20
Total with taxes and fees
Candlewood Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
3.9 mi from Annapolis Sailing School
8.8 out of 10, Excellent, (1009)
"Excellent from check in to check out, highly recommend!"
United States
Eric
$97 nightly
The price is $111
Dec 15 - Dec 16
Total with taxes and fees
Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
4.1 mi from Annapolis Sailing School
8.8 out of 10, Excellent, (962)
"Nice breakfast, clean room, great parking"
United States
Amy
$91 nightly
The price is $104
Dec 30 - Dec 31
Total with taxes and fees
Sonesta ES Suites Annapolis

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
8.1 mi from Annapolis Sailing School
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
$207 nightly
The price is $230
Dec 14 - Dec 15
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
3.9 mi from Annapolis Sailing School
8.6 out of 10, Excellent, (1000)
"Great place!"
United States
Tawnya
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
4.2 mi from Annapolis Sailing School
8.6 out of 10, Excellent, (1001)
"Wonderful stay. "
United States
Angela
$84 nightly
The price is $96
Dec 28 - Dec 29
Total with taxes and fees
Courtyard by Marriott Annapolis

Kent Island Resort

Kent Island Resort
3.5 star property
8.2 mi from Annapolis Sailing School
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$163 nightly
The price is $177
Dec 11 - Dec 12
Total with taxes and fees
Kent Island Resort

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
3.7 mi from Annapolis Sailing School
8.2 out of 10, Very Good, (1000)
"Clean room and friendly staff! "
United States
Silvia
$80 nightly
The price is $91
Dec 20 - Dec 21
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
4 mi from Annapolis Sailing School
8.2 out of 10, Very Good, (1003)
"I had a great experience at my stay at Hampton "
United States
Idris O
$90 nightly
The price is $103
Dec 17 - Dec 18
Total with taxes and fees
Hampton Inn & Suites Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
4.3 mi from Annapolis Sailing School
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Annapolis
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

Hotels near other Annapolis Sailing School attractions

Frequently asked questions

What are the top-rated hotels near Annapolis Sailing School?
Discover the top-rated hotels near Annapolis Sailing School that provide exceptional comfort and a perfect getaway experience.

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel boasts an impressive review rating of 10 and is situated just 4.5 miles from Annapolis Sailing School. This luxury boutique hotel offers a romantic atmosphere complemented by amenities such as complimentary toiletries, valet parking, and early check-in options. Guests can also enjoy Champagne service, enhancing their stay with a touch of elegance.

Charming Annapolis Guest House

Charming Annapolis Guest House is a delightful 3-star hotel with a perfect review rating of 10, located only 4.3 miles from Annapolis Sailing School. This traveler house features well-equipped kitchenettes and spacious dining areas, making it ideal for travelers who appreciate the comforts of home. Amenities include air conditioning, onsite parking, and a full kitchen, ensuring a cozy and convenient stay.

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel offers a high-end experience with a review rating of 9.6, positioned just 4.2 miles from Annapolis Sailing School. This hotel stands out with its luxurious features, including a private hot tub and daily complimentary breakfast. Guests can enjoy the serene garden, designer toiletries, and premium bedding, ensuring a luxurious and comfortable stay.
How much is a hotel near Annapolis Sailing School?
Staying near Annapolis Sailing School is a treat, with plenty of hotels from $85 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a vacation during weekends or around public holidays.
What are the most popular family-friendly hotels near Annapolis Sailing School?
For families seeking the perfect stay near Annapolis Sailing School, these top-rated hotels offer family-friendly amenities and comfort for an enjoyable getaway.

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis, situated 4.6 miles from Annapolis Sailing School, is an excellent 4-star option with an impressive review rating of 9.4. Families will appreciate the amenities such as free rollaway beds, daily housekeeping, and a dedicated snack bar. With additional features like onsite bicycle rentals, a 24-hour fitness center, and nearby kayaking, this hotel ensures a fun and active stay for travelers of all ages.

Historic Inns of Annapolis

Historic Inns of Annapolis offers a charming stay 4.5 miles from Annapolis Sailing School, with a fantastic review rating of 9.0. This 3.5-star hotel is family-friendly, providing amenities like free cribs, daily housekeeping, and special breakfasts for children. Guests can explore the historic charm while enjoying the terrace, valet parking, and 24-hour fitness access, perfect for families looking for both comfort and a touch of history.

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection is a delightful 4-star choice just 4.0 miles from Annapolis Sailing School. With a great traveler rating score of 8.8, this hotel caters perfectly to families with amenities like free cribs, connecting rooms, and daily housekeeping. Guests can enjoy the scenic rooftop garden, on-site sailing, and 24-hour fitness facilities, ensuring a comfortable and engaging stay.
Which hotels near Annapolis Sailing School offer the best views?
Discover some of the best hotels with stunning views near Annapolis Sailing School that will elevate your stay in Annapolis.

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection is a luxurious 4-star retreat located just 4.0 miles from Annapolis Sailing School, with an impressive review rating of 8.8. This hotel is perfect for travelers seeking a waterfront experience, featuring a beautiful terrace and furnished balconies that offer ocean views. Guests can enjoy a rooftop garden, 24-hour fitness facilities, and easy access to nearby sailing tours. The hotel also provides valet parking and designer toiletries, ensuring a comfortable stay.
What are the best affordable hotels near Annapolis Sailing School?
For travelers seeking affordable yet charming accommodations near Annapolis Sailing School, these options provide top-rated experiences without breaking the bank.

86 State Circle - Luxury Boutique Hotel

Located just 4.5 miles from Annapolis Sailing School, 86 State Circle is a luxurious boutique hotel with a perfect travelers' rating of 10. Guests enjoy complimentary toiletries and WiFi, along with late check-out and covered valet parking. Nestled in a historical district, this hotel also offers a romantic ambiance and concierge services, making it a delightful choice for visitors.

Charming Annapolis Guest House

Charming Annapolis Guest House, a cozy 3-star hotel located 4.3 miles from Annapolis Sailing School, boasts a perfect review rating of 10. This traveler house features in-room kitchenettes, allowing travelers to prepare their own meals, as well as complimentary WiFi. Additional amenities include onsite parking and air conditioning, ensuring a comfortable and convenient stay.

134 Prince - Luxury Boutique Hotel

Just 4.2 miles from Annapolis Sailing School, 134 Prince is a luxurious boutique hotel rated 9.6 by travelers. Guests can enjoy a range of complimentary amenities, including WiFi, a stocked minibar, and daily breakfast. With features such as a hot tub, shared refrigerator, and valet parking, this hotel combines comfort and elegance for a memorable stay.
Are there any hotels with pools close to Annapolis Sailing School?
Discover the ideal hotels with pools near Annapolis Sailing School, perfect for a refreshing stay after a day on the water.

The Westin Annapolis

The Westin Annapolis is a stylish 4-star hotel located just 4.6 miles from Annapolis Sailing School, with an excellent review rating of 8.6. Guests can enjoy the indoor pool, which is accessible, along with a range of rejuvenating spa services including massages and aromatherapy treatments. Additional amenities include a 24-hour fitness center, valet parking, and an on-site restaurant that caters to families with kids' meals. This hotel combines comfort and convenience, making it a great choice for those looking to unwind after sailing.
What are the best pet-friendly hotels near Annapolis Sailing School?
For those looking for top-rated pet-friendly hotels near Annapolis Sailing School, there are fantastic options that ensure both you and your furry friend have a comfortable stay.

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis, rated 9.4 by travelers, is a 4-star hotel located just 4.6 miles from Annapolis Sailing School. This hotel welcomes pets with amenities such as food and water bowls and permits pets in rooms. Guests can also enjoy a variety of features including a fitness center open 24 hours, valet parking, and nearby kayaking and boating activities, making it an excellent option for travelers with pets who enjoy adventure.

The Westin Annapolis

The Westin Annapolis is another impressive choice, an 8.6 traveler rating and a 4-star designation, situated 4.6 miles from Annapolis Sailing School. This hotel allows dogs and features a range of pet-friendly amenities. Guests can indulge in the onsite spa and indoor pool, while also enjoying convenient access to the historical district and local shopping. The Westin combines relaxation with adventure, perfect for travelers traveling with their pets.

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown is a welcoming 3-star hotel just 4.8 miles from Annapolis Sailing School, with a solid review rating of 8.6. This hotel accommodates pets and offers amenities like in-room refrigerators and microwaves, making it a comfortable home away from home. Guests can unwind on the terrace or explore nearby hiking and biking trails, ensuring a fun and flexible stay for both pets and their owners.
Can I book a fully refundable hotel close to Annapolis Sailing School?
Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Annapolis Sailing School", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.
Can I find Expedia discounts for hotels near Annapolis Sailing School?
To look for discounts on hotels near Annapolis Sailing School, join One Key™—our free travel rewards program. One Key members always get our best prices and earn OneKeyCash™* on eligible bookings for every dollar spent. Another way to save is by bundling your hotel and flights together on Expedia.

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