Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
In two weeks

Where to stay in Chester?

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,004 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
Jul 6 - Jul 7
St Michaels Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (929 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
Jul 12 - Jul 13
Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,005 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 $125
$139 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Kent Narrows Inn

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,000 reviews)
Wake up to a delicious free breakfast at this welcoming Easton hotel before enjoying a refreshing dip in the indoor pool. With free WiFi, parking, and fitness center, you'll be minutes from Talbot Massage and local attractions.
The price is $139
$153 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Plus Easton Inn & Suites

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (152 reviews)
The price is $145
$195 total
includes taxes & fees
Jul 5 - Jul 6
Kent Island Resort

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (896 reviews)
Relax in this quiet Easton hotel where travelers praise the peaceful environment. Take a refreshing dip in the seasonal pool or maintain your routine at the fitness center. With free breakfast, WiFi, and parking, you'll have easy access to local attractions.
The price is $101
$111 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,005 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 $95
$109 total
includes taxes & fees
Jul 5 - Jul 6
DoubleTree by Hilton Hotel Annapolis

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (895 reviews)
Immerse yourself in this charming hotel with a full-service spa offering massages and facials. Enjoy local flavors at Hunters' Tavern, then unwind at the bar or terrace. Just minutes from Avalon Theatre and Customs House with free WiFi and parking.
The price is $159
$175 total
includes taxes & fees
Aug 2 - Aug 3
The Tidewater Inn

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (614 reviews)
Wake up to a complimentary breakfast before exploring Easton's charming sights. This hotel's indoor pool invites year-round relaxation, while the 24-hour fitness center keeps workout routines on track. Just 4 minutes from Easton-Newnam Airport with free parking and WiFi.
The price is $155
$171 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express Easton by IHG

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
The price is $83
$95 total
includes taxes & fees
Jul 6 - Jul 7
Village Inn Annapolis MD

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,001 reviews)
The price is $100
$114 total
includes taxes & fees
Jul 12 - Jul 13
Hilton Garden Inn Annapolis

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (491 reviews)
The price is $269
$307 total
includes taxes & fees
Jul 6 - Jul 7
Anchored Inn at Hidden Harbour Marina

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,001 reviews)
The price is $92
$105 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Annapolis

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (393 reviews)
This motel offers a budget-friendly base in Easton with convenient free perks including continental breakfast, WiFi, and parking. Located near Easton Cycle and Sport, you'll find Talbot Massage just moments away for post-adventure relaxation.
The price is $85
$94 total
includes taxes & fees
Jul 16 - Jul 17
Econo Lodge Easton Route 50

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (65 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 $178
$198 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Huntingfield Creek

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (574 reviews)
This business-friendly hotel features a morning swim spot and fitness center that travelers appreciate. Located near Easton Cycle and Sport and the Rail Depot, it offers free breakfast, WiFi, and parking with staff known for their helpfulness.
The price is $128
$141 total
includes taxes & fees
Jul 19 - Jul 20
Hampton Inn Easton

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,867 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 $100
$148 total
includes taxes & fees
Jul 13 - Jul 14
Historic Inns of Annapolis

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (378 reviews)
Wake up refreshed at this welcoming Easton hotel featuring complimentary breakfast and parking. After a morning workout in the fitness center, cool off in the indoor pool. Rooms include microwaves and refrigerators, while the helpful staff ensures a pleasant stay.
The price is $135
$149 total
includes taxes & fees
Jul 12 - Jul 13
Fairfield Inn & Suites by Marriott Easton

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, (1,003 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 $139
$154 total
includes taxes & fees
Jul 23 - Jul 24
Holiday Inn Express Annapolis East-Kent Island by IHG

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (140 reviews)
This waterfront inn on Tilghman Island features a seasonal outdoor pool and welcoming restaurant with bar. Near local marinas, it offers free breakfast, WiFi, and parking. Guests can relax on the terrace or stroll through the garden while experiencing exceptional staff service.
The price is $225
$248 total
includes taxes & fees
Jul 20 - Jul 21
The Tilghman Island Inn
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 Northern Chesapeake Bay.

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 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.