Hotels in Chester

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Where to stay in Chester?

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 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
Jun 17 - Jun 18
Quality Inn Grasonville near Kent Island

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (885 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 1 - Jul 2
Quality Inn

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (605 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 $140
$154 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Express Easton by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 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 $110
$122 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,001 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 $128
$141 total
includes taxes & fees
Jun 15 - Jun 16
St Michaels Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (143 reviews)
The price is $153
$204 total
includes taxes & fees
Jun 15 - Jun 16
Kent Island Resort

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,005 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
Jun 14 - Jun 15
Best Western Plus Easton Inn & Suites

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (392 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 $81
$89 total
includes taxes & fees
Jun 17 - Jun 18
Econo Lodge Easton Route 50

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 reviews)
Set on the bay, this Tilghman hotel offers waterfront relaxation with complimentary breakfast and free parking. Explore by kayak or bicycle with onsite rentals, or unwind at the marina. Each room includes convenient refrigerators and microwaves for added comfort.
The price is $150
$165 total
includes taxes & fees
Jun 15 - Jun 16
Knapps Narrows Marina & Inn

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,005 reviews)
The price is $97
$110 total
includes taxes & fees
Jun 17 - Jun 18
Hilton Garden Inn Annapolis

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (571 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 $146
$161 total
includes taxes & fees
Jun 21 - Jun 22
Hampton Inn Easton

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,015 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 $111
$127 total
includes taxes & fees
Jun 15 - Jun 16
DoubleTree by Hilton Hotel Annapolis

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 $134
$149 total
includes taxes & fees
Jun 16 - Jun 17
Holiday Inn Express Annapolis East-Kent Island by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
9.0 out of 10, Wonderful, (263 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 $93
$111 total
includes taxes & fees
Jun 15 - Jun 16
Candlewood Suites Annapolis by IHG

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (487 reviews)
The price is $269
$307 total
includes taxes & fees
Jun 14 - Jun 15
Anchored Inn at Hidden Harbour Marina

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, (1,036 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 $97
$110 total
includes taxes & fees
Jun 21 - Jun 22
Country Inn & Suites by Radisson, Annapolis, MD

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (64 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
Jun 14 - Jun 15
Inn at Huntingfield Creek

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,011 reviews)
The price is $83
$94 total
includes taxes & fees
Jun 14 - Jun 15
Best Western Annapolis

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (169 reviews)
Waterfront hotel in Oxford offers complimentary breakfast and parking, plus in-room refrigerators and microwaves for added convenience. Explore nearby Oxford Museum, or simply unwind on the terrace overlooking the bay.
The price is $199
$219 total
includes taxes & fees
Jun 15 - Jun 16
Sandaway Suites & Beach

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
Jul 6 - Jul 7
Hilton Garden Inn Kent Island Marina
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.

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 9 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.