Photo by Patricia Knorr

Chester Hotel Guide - 4 Stars Hotels in Chester, Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Top Chester 4 Star Hotels

DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"Excellent hospitable staff made the stay even better!"
The price is Rp1.666.782
Rp1.900.132 total
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1014)
"Great stay! Would come here again."
The price is Rp2.532.528
Rp2.887.082 total
includes taxes & fees
3 Aug - 4 Aug
Graduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (839)
"Front desk staff was very friendly and helpful."
The price is Rp3.585.583
Rp4.087.565 total
includes taxes & fees
24 Jul - 25 Jul
Annapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is Rp2.598.219
Rp2.961.970 total
includes taxes & fees
10 Aug - 11 Aug
The Westin Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (401)
"Staff was very polite and friendly. "
The price is Rp3.501.705
Rp4.301.233 total
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is Rp6.728.160
Rp7.400.976 total
includes taxes & fees
20 Jul - 21 Jul
The Oaks Waterfront
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

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

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD
The price is Rp10.334.101 per night from 24 Jul to 25 Jul
Rp10.334.101
Rp12.504.344 total
24 Jul - 25 Jul
includes taxes & fees
9.4/10 Exceptional! (355 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in Chester?
Expedia customers give top marks to The Inn at Chesapeake Bay Beach Club. From its handy amenities to its attentive staff, every aspect of this 4-star hotel in Chester is designed to deliver an incredible holiday experience.
How much does it cost to stay in a 4-star hotel in Chester?
To find a 4-star hotel in Chester that fits your budget, use Expedia's handy search filters. Take a look at the available options during your holiday dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly escape first.

  • Search for the lowest price from Rp10.334.101

What's the difference between 5-star and 4-star hotels in Chester?
If you choose to holiday at a 4-star hotel in Chester, you'll usually find plenty of amenities to keep you relaxed, such as a gym, restaurant and pool. You can enjoy top-quality service and upmarket accommodation. Opt for a 5-star hotel and you'll have access to a few extra perks --- think on-site spas, 24-hour front desk and nightly turndown services. You're likely to get more amenities and first-class services at a 5-star retreat, though both are fabulous options for luxury guests.