Hotels in Highland Beach
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Rod 'N' Reel Resort
Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1003)
8.4/10
Very Good
(1003)
The price is $101
$101
$132 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (941)
9.2/10
Wonderful
(941)
- Escape to scenic Kent Island where bay views and bike trails await your morning coffee.
The price is $79
$79
$88 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
7.8/10
Good
(863)
- A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $84
$84
$93 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
9.2/10
Wonderful
(130)
The price is $128
$128
$177 total
includes taxes & fees
Dec 29 - Dec 30
St Michaels Inn
St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
8.2/10
Very Good
(1001)
- Relax in a peaceful inn near St. Michaels Village with a seasonal outdoor pool.
The price is $101
$101
$111 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
8.6/10
Excellent
(1005)
- Contemporary hotel near U.S. Naval Academy with fitness center and garden.
The price is $75
$75
$85 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
8.0/10
Very Good
(1002)
- Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $83
$83
$93 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (680)
9.6/10
Exceptional
(680)
- Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $116
$116
$129 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (182)
8.8/10
Excellent
(182)
- Boutique lodging near Annapolis Harbor with peaceful environment and hiking trails.
The price is $80
$80
$91 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn Conference Center
Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1002)
9.2/10
Wonderful
(1002)
- Convenient Bowie hotel with seasonal pool and cozy dining near Allen Pond Park.
The price is $99
$99
$112 total
includes taxes & fees
Dec 29 - Dec 30
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1005)
8.2/10
Very Good
(1005)
- Enjoy Naval Academy access and seasonal outdoor swim in Maryland's historic capital.
The price is $81
$81
$93 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Microtel Inn & Suites by Wyndham Gambrills
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1005)
9.0/10
Wonderful
(1005)
- Modern lodgings with convenient free parking near Regal Waugh Chapel.
The price is $76
$76
$87 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
- Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $114
$114
$127 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1005)
9.0/10
Wonderful
(1005)
- Country Inn and Suites provides peaceful stays near Annapolis attractions.
The price is $94
$94
$107 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1001)
8.2/10
Very Good
(1001)
- Experience Annapolis with effortless access to Naval Academy and local dining spots.
The price is $80
$80
$91 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
8.8/10
Excellent
(90)
The price is $118
$118
$174 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Annapolis
Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1001)
7.8/10
Good
(1001)
The price is $68
$68
$78 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Courtyard by Marriott Annapolis
Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
- Explore Annapolis from a convenient location with an indoor pool and bistro.
The price is $84
$84
$96 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (363)
9.4/10
Exceptional
(363)
- Enjoy Chesapeake Bay marina views with kayaking and seasonal outdoor pool.
The price is $120
$120
$132 total
includes taxes & fees
Dec 29 - Dec 30
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (471)
9.4/10
Exceptional
(471)
The price is $149
$149
$170 total
includes taxes & fees
Dec 29 - Dec 30
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.
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.
Go beyond your typical stay in Highland Beach
Pet friendly
Family friendly
Cottage
Check out reviews of Highland Beach hotels guests love
SpringHill Suites by Marriott Annapolis
10/10 Excellent
"I REALLY ENJOYED MY STAY, CLEAN, NICE SETUP AND THE AMENTIES WERE GREAT I LOVED IT"
Crowne Plaza Annapolis by IHG
10/10 Excellent
"Yes!"
Microtel Inn & Suites by Wyndham Gambrills
10/10 Excellent
"Nice spacious room for the rate. The room
was clean."
Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
"Lovely small picturesque hotel for Christmas with excellent breakfast buffet."
Hilton Garden Inn Annapolis Downtown
10/10 Excellent
"Everything good, staff excellent. "
Hyatt Place Kent Narrows & Marina
10/10 Excellent
"Spotless rooms, outstanding staff, incredible view "
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"did not dine in your hotel. "
Comfort Inn Conference Center
10/10 Excellent
"Clean and excellent bedding."
Historic Inns of Annapolis
10/10 Excellent
"Best place to stay is the main building"
Frequently asked questions
What accommodations do travelers recommend in Highland Beach?
Can I book a refundable hotel in Highland Beach?
If you're looking for the flexibility to change your travel plans to Highland Beach, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Highland Beach be like during my visit?
July and August are typically the warmest months in Highland Beach when the average temp is 75°F. January and February are the coldest months when the average temperature is 40°F. July and September are the months with the most rain.
Why should I book my Highland Beach accommodation with Hotels.com?
There are lots of reasons to book your Highland Beach trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.