Explore top 2026 4 Star Hotels in Shady Side

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Top Shady Side 4 Star hotels

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $111 total per night from May 31 to Jun 1
$111 total
May 31 - Jun 1
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
8.8/10 Excellent! (1,000 reviews)
"Staff was very help."

Reviewed on May 25, 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Jun 11 to Jun 12
$138 total
Jun 11 - Jun 12
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. ...
8.2/10 Very Good! (1,001 reviews)
"Unfortunately, our stay was not a good experience due to the condition of the hotel. The AC was not working properly, and the room smelled like there had been ongoing water leakage or moisture issues. The beds were also very uncomfortable and felt as if you would roll toward the middle. That being ..."

Reviewed on May 27, 2026

Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Jun 7 to Jun 8
$193 total
Jun 7 - Jun 8
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business ...
8.8/10 Excellent! (1,002 reviews)
"clean room, restaurant and bar on premises, easy parking"

Reviewed on May 27, 2026

Opens in a new windowThe Westin Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $186 total per night from Jun 7 to Jun 8
$186 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...
9.4/10 Exceptional! (1,006 reviews)
"Loved the Navy inspired decor and theme, location, valet parking, bathroom accouterments. Would definitely choose The Graduate again.."

Reviewed on May 28, 2026

Opens in a new windowGraduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $208 total per night from Jun 3 to Jun 4
$208 total
Jun 3 - Jun 4
Total with taxes and fees
A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax ...
8.6/10 Excellent! (1,002 reviews)
"Beautiful hotel. We stayed a couple days for a wedding in the area. We had a beautiful deck with a beautiful view. We were in 227. The area was great for walks. The staff was friendly and helpful."

Reviewed on May 27, 2026

Opens in a new windowRod 'N' Reel Resort
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $251 total per night from Jun 7 to Jun 8
$251 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
8.8/10 Excellent! (930 reviews)
"It's"

Reviewed on May 18, 2026

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $276 total per night from Jun 15 to Jun 16
$276 total
Jun 15 - Jun 16
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this traditional hotel. Enjoy the seasonal outdoor pool and perks like free self parking ...
9.4/10 Exceptional! (455 reviews)
"The entire place was beautiful, the staff, room, shops, restaurants all were amazing. Thanks"

Reviewed on May 27, 2026

Opens in a new windowThe Inn at Chesapeake Bay Beach Club
The Oaks Waterfront

The Oaks Waterfront

4 out of 5
25876 Royal Oak Road Easton MD
Fully refundableReserve now, pay when you stay
$489 nightly
The price is $538 total per night from May 31 to Jun 1
$538 total
May 31 - Jun 1
Total with taxes and fees
This bed & breakfast features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and free perks like cooked-to-order breakfast ...
10/10 Exceptional! (41 reviews)
"Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return."

Reviewed on Nov 28, 2025

Opens in a new windowThe Oaks Waterfront
Legacy Villa

Legacy Villa

4 out of 5
12605 Brooke Lane Upper Marlboro MD
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. WiFi in public areas is free. A garden, a picnic area, ...
Get rates
Opens in a new windowLegacy Villa
Don't see what you're looking for?
See all available properties in Shady Side
View all properties
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.

4 Star Hotels Shady Side

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Shady Side 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Shady Side will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Shady Side, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Shady Side hotel reviews by fellow wanderers

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"I recently stayed at La Quinta Hotel and overall had a positive experience. I checked in late & as I inspected the room, I noticed there was a leak coming from the sink. I reported the issue to the front desk & he was very understanding, informing me that since it was late, maintenance would come by the following morning to repair it. Although I did have to follow up with the front desk the next day, I was satisfied that within about 10 minutes, maintenance arrived & fixed the leak without me having to change rooms. I especially want to recognize the front desk night auditor for taking my concern seriously, not disregarding my complaint & handling the situation professionally & respectfully."
A verified traveler stayed at La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Explore More Ways to Travel with Travelocity