A river with boats, a marina, and a town with houses and buildings.

Shady Side 4 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side 4 Star Hotels

Tonight
Sep 19 - Sep 20
Tomorrow
Sep 20 - Sep 21
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Shady Side 4-star hotels

Reception
Bar (on property)
Lobby
Lobby

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Chereis
NT$2,640
NT$3,009 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Hotel Annapolis
View from property
Bar (on property)
Lobby
Lobby

2. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Boryana
NT$4,743
NT$5,407 total
includes taxes & fees
Sep 27 - Sep 28
Graduate by Hilton Annapolis
Lobby
Bar (on property)
Property amenity
Lobby

3. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
NT$5,697
NT$6,494 total
includes taxes & fees
Sep 27 - Sep 28
The Westin Annapolis
Exterior
Bar (on property)
Indoor pool
Reception

4. DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC
Upper Marlboro
United States
Glen
NT$3,627
NT$4,099 total
includes taxes & fees
Oct 4 - Oct 5
DoubleTree by Hilton Hotel Largo/Washington DC
Outdoor wedding area
Coffee shop
2 bars/lounges
Hair salon

5. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
NT$4,601
NT$6,167 total
includes taxes & fees
Oct 7 - Oct 8
Rod 'N' Reel Resort
Premium bedding, down comforters, pillowtop beds, in-room safe
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe
Exterior
Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe

6. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
NT$7,358
NT$8,388 total
includes taxes & fees
Oct 4 - Oct 5
Annapolis Waterfront Hotel, Autograph Collection
Front of property - evening/night
Garden
Ballroom
Dining

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
NT$6,086
NT$7,565 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
Luxury Suite, 1 Bedroom, Balcony | Balcony view
Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, WiFi (free), bed sheets
Indoor wedding

8. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
NT$14,006
NT$15,406 total
includes taxes & fees
Sep 24 - Sep 25
The Oaks Waterfront
Family House | In-room dining
In-room dining
Exterior
Exterior

9. Legacy Villa

Legacy Villa
Upper Marlboro
Legacy Villa
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shady Side.
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
NT$19,190
NT$21,109 total
Oct 13 - Oct 14
includes taxes & fees
9.6/10 Exceptional! (402 reviews)
Inn at Perry Cabin
The Inn at Tacaro Estate

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD
NT$12,622
NT$14,390 total
Sep 27 - Sep 28
includes taxes & fees
9.6/10 Exceptional! (19 reviews)
The Inn at Tacaro Estate
Still don't see what you're looking for?
See all properties in Shady Side.
You can also use these popular filters to refine your search.
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.

Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"Good stay"
Glen 4-night trip
Posted 5 days ago
DoubleTree by Hilton Hotel Largo/Washington DC
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"This is a great hotel in a great location two great restaurants."
William 1-night trip
Posted 5 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Shady Side?
With Expedia's handy filter tool, scoring a superb deal on a 4-star hotel in Shady Side just got simpler. Start by keying in your chosen travel dates and length of your vacation. Then list the results by price and choose a hotel that best suits your budget and style.
  • Search for the lowest price from NT$14,390
What's the difference between 5-star and 4-star hotels in Shady Side?
Give yourself the luxury treatment during your Shady Side escape by staying at a 4-star hotel. As well as featuring upscale surroundings, these properties are typically filled with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your stay an even more lavish and special one. Concierge assistance, luxurious spas and gourmet dining are only the start of the exclusive services and conveniences you'll likely get access to.
Does Shady Side have any 4-star all-inclusive resorts?
Finding your dream vacation in Shady Side is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, food and activities, or opt for a standard 4-star resort in or around this leading destination.

Explore a world of travel with Expedia