Hotels in Chester

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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, (1,001 reviews)
Wake up to tranquil Chesapeake Bay vistas at this quiet waterfront retreat. Steps from the scenic bike trail with an inviting seasonal pool for afternoon dips. Complimentary breakfast fuels adventures to nearby Environmental Center and Queenstown Harbor Golf Club.
The price is $100
$111 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,000 reviews)
Embrace coastal charm at this hotel in Grasonville, where superior rooms frame magical sunset vistas over the water. After exploring nearby walking trails, unwind in the indoor pool, hot tub, or sauna. Free breakfast fuels adventures to local restaurants.
The price is $115
$127 total
includes taxes & fees
Jul 28 - Jul 29
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (791 reviews)
Experience coastal luxury at this modern Kent Narrows hotel with marina access. A 24-hour fitness center, bar, and café await after exploring nearby Chesapeake Bay Environmental Center. The helpful staff and convenient location make for an exceptional stay.
The price is $169
$188 total
includes taxes & fees
Jul 29 - Jul 30
Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
Overlooking the bay in Grasonville, this hotel offers a refreshing indoor pool, restaurant, and bar. Unwind on the terrace after exploring nearby Chesapeake Bay Environmental Center, with convenient room service and in-room microwaves for added comfort.
The price is $147
$163 total
includes taxes & fees
Aug 2 - Aug 3
Hilton Garden Inn Kent Island Marina

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (165 reviews)
The price is $147
$197 total
includes taxes & fees
Aug 5 - Aug 6
Kent Island Resort

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (940 reviews)
Discover quiet comfort at this Grasonville hotel with complimentary buffet breakfast, WiFi, and parking. Take a refreshing swim in the seasonal outdoor pool after exploring nearby Chesapeake Bay Environmental Center. Friendly staff and clean rooms await just 50 minutes from BWI Airport.
The price is $100
$111 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn Grasonville near Kent Island

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (468 reviews)
Escape to this serene Chesapeake retreat featuring an outdoor pool and indulgent spa treatments. Just minutes from Northern Chesapeake Bay and Paul Reed Smith Guitars, the hotel offers a cafe, 24-hour fitness center, and attentive staff that guests consistently praise.
The price is $236
$287 total
includes taxes & fees
Aug 3 - Aug 4
The Inn at Chesapeake Bay Beach Club

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,003 reviews)
Escape to this quiet retreat with hiking trails and a garden terrace. Just minutes from Saint Michaels Village and Classic Motor Museum, this hotel offers free breakfast, WiFi and parking. Guests consistently praise the helpful staff and clean accommodations.
The price is $105
$116 total
includes taxes & fees
Aug 16 - Aug 17
St Michaels Inn

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (512 reviews)
The price is $83
$95 total
includes taxes & fees
Jul 27 - Jul 28
Village Inn Annapolis MD

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, (1,048 reviews)
Enjoy serene accommodations with an indoor pool and hot tub just 10 minutes from U.S. Naval Academy. This hotel offers complimentary breakfast, WiFi, and parking near Annapolis Bowl and Westfield Mall, earning praise for its helpful staff and quiet atmosphere.
The price is $105
$120 total
includes taxes & fees
Jul 30 - Jul 31
Country Inn & Suites by Radisson, Annapolis, MD

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, (1,005 reviews)
Wake up to a complimentary buffet breakfast at this conveniently located hotel near U.S. Naval Academy. Enjoy free WiFi and parking while exploring nearby restaurants and shops. The 24-hour fitness center keeps your routine intact during your stay.
The price is $96
$110 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express & Suites Annapolis by IHG

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,007 reviews)
The price is $81
$92 total
includes taxes & fees
Jul 27 - Jul 28
Best Western Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,896 reviews)
Nestled in the heart of Annapolis, this historic hotel offers easy access to the Naval Academy. Unwind in comfortable beds after exploring nearby attractions, or enjoy a drink at the bar. The helpful staff and clean rooms earn high praise from travelers.
The price is $118
$169 total
includes taxes & fees
Jul 28 - Jul 29
Historic Inns of Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,000 reviews)
The price is $98
$111 total
includes taxes & fees
Aug 2 - Aug 3
Hilton Garden Inn Annapolis

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (68 reviews)
Surrounded by garden landscapes, this waterfront B&B features in-room refrigerators and laundry amenities. After enjoying the complimentary breakfast, relax by the outdoor pool or book a massage at the spa, just minutes from Rock Hall Harbor.
The price is $200
$223 total
includes taxes & fees
Jul 23 - Jul 24
Inn at Huntingfield Creek

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (282 reviews)
Just 10 minutes from U.S. Naval Academy, this quiet hotel offers free WiFi and parking for easy exploration. After a day of nearby kayaking or hiking trails, unwind in the 24-hour fitness center. Travelers consistently praise the helpful staff and convenient location.
The price is $88
$105 total
includes taxes & fees
Jul 28 - Jul 29
Candlewood Suites Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,046 reviews)
Just a 5-minute drive from U.S. Naval Academy, this hotel offers a 24-hour fitness center and Ports of Call restaurant. Annapolis Harbor Center and Westfield Mall are nearby, with free WiFi and parking for your convenience.
The price is $103
$117 total
includes taxes & fees
Aug 16 - Aug 17
DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,002 reviews)
Stay at this central Annapolis hotel, just 10 minutes from U.S. Naval Academy. The indoor pool and hot tub offer relaxation after exploring nearby harbors. Grab American cuisine at The Bistro or unwind in clean, quiet rooms with free WiFi and parking.
The price is $106
$121 total
includes taxes & fees
Jul 29 - Jul 30
Courtyard by Marriott Annapolis

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,006 reviews)
Explore downtown Annapolis from this stylish Art Deco hotel with Kitchen on West St serving regional cuisine. The 24-hour fitness center, in-room refrigerators, and microwaves enhance your stay near Annapolis Civil Rights Plaque.
The price is $106
$121 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Annapolis Downtown

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1,001 reviews)
Located just a short drive from the U.S. Naval Academy, this family-friendly hotel offers a seasonal outdoor pool and fitness center. Guests love the helpful staff and free breakfast. Annapolis Harbor Center Shopping Center is nearby for convenient retail therapy.
The price is $98
$111 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn & Suites 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 landmarks in Chester

Learn more about Chester

The region around Chester is home to attractions such as Chesapeake Exploration Center and Paul Reed Smith Guitars.

A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Check out reviews of Chester hotels guests love

Frequently asked questions

What accommodations do travelers recommend in Chester?
Can I book a refundable accommodation in Chester?
If you're looking for the flexibility to change your travel plans to Chester, most properties provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Chester if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 8 vacation homes.
What will the weather in Chester be like during my visit?
July and August are typically the warmest months in Chester when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. July and October are the months with the most rain.
Why should I book my Chester hotel through Hotels.com?
There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Keyâ„¢, our rewards program, you will be able to earn and use OneKeyCashâ„¢* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.