Hotels in Chester

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Check prices for these dates

Tonight
Apr 19 - Apr 20
Tomorrow
Apr 20 - Apr 21
Next weekend
Apr 24 - Apr 26
In two weeks
May 1 - May 3

Where to stay in Chester?

Desk, free WiFi, bed sheets
Econo Lodge Easton Route 50
Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (389 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
Apr 26 - Apr 27
Econo Lodge Easton Route 50
Bar (on property)
Hampton Inn Easton
Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (563 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 $144
$158 total
includes taxes & fees
Apr 26 - Apr 27
Hampton Inn Easton
Exterior
Quality Inn
Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (857 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 $81
$89 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn
Lobby
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,003 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 $109
$120 total
includes taxes & fees
Apr 21 - Apr 22
Best Western Plus Easton Inn & Suites
Free daily buffet breakfast
Holiday Inn Express Easton by IHG
Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (601 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
Apr 21 - Apr 22
Holiday Inn Express Easton by IHG
Lobby
Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (370 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
Apr 26 - Apr 27
Fairfield Inn & Suites by Marriott Easton
Front of property
Hummingbird Inn
Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (89 reviews)
Escape to this Victorian bed & breakfast in Easton where pampering awaits at the on-site spa. Each room includes convenient refrigerators and microwaves. Enjoy the hot tub, 24-hour fitness center, free breakfast, and parking while exploring nearby Avalon Theatre.
The price is $329
$362 total
includes taxes & fees
Apr 21 - Apr 22
Hummingbird Inn
Meeting facility
The Tidewater Inn
The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (869 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 $169
$186 total
includes taxes & fees
Apr 21 - Apr 22
The Tidewater Inn
Property grounds
Sandaway Suites & Beach
Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (157 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 $191
$210 total
includes taxes & fees
Apr 22 - Apr 23
Sandaway Suites & Beach
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
The Oaks Waterfront
The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
Overlooking the water from a rooftop terrace, this charming B&B in Easton offers massage services and seasonal poolside relaxation. Explore nearby Saint Michaels Village after enjoying free breakfast. The garden setting and helpful staff create a memorable Eastern Shore experience.
The price is $489
$538 total
includes taxes & fees
Apr 21 - Apr 22
The Oaks Waterfront
Front of property
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 $129
$142 total
includes taxes & fees
Apr 21 - Apr 22
St Michaels Inn
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin
Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
Set along Maryland's Eastern Shore, this luxurious retreat features a marina, golf course, and serene spa treatments. Enjoy cocktails at the poolside bar before savoring locally-inspired cuisine at Stars restaurant. The helpful staff ensures a peaceful waterfront getaway.
The price is $572
$629 total
includes taxes & fees
Apr 23 - Apr 24
Inn at Perry Cabin
Front of property
The Wildset
The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (432 reviews)
Soak in the charm of this waterfront getaway near Higgins Yacht Yard and Marina. Enjoy complimentary breakfast before exploring Muskrat Park. After sightseeing, unwind with drinks at the bar or grab a bite at the on-site café.
The price is $229
$274 total
includes taxes & fees
Apr 21 - Apr 22
The Wildset
Porch
Parsonage Inn
Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
Immerse yourself in small-town charm at this cozy B&B featuring a lovely garden and terrace. Enjoy complimentary full breakfast daily before exploring nearby hiking trails or Perry Cabin Park. Free WiFi and parking complete your Eastern Shore retreat.
The price is $169
$186 total
includes taxes & fees
Apr 21 - Apr 22
Parsonage Inn
Exterior
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (72 reviews)
Surrounded by coastal beauty, this Victorian B&B offers a refreshing outdoor pool and free breakfast in St. Michaels. Explore nearby Perry Cabin Park or hike local trails, then unwind in the garden or terrace after your adventures.
The price is $270
$297 total
includes taxes & fees
Apr 24 - Apr 25
George Brooks House B&B
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (895 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 $106
$118 total
includes taxes & fees
Apr 22 - Apr 23
Quality Inn Grasonville near Kent Island
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 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 $130
$145 total
includes taxes & fees
Apr 26 - Apr 27
Hilton Garden Inn Kent Island Marina
Exterior
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, (989 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 $125
$139 total
includes taxes & fees
Apr 26 - Apr 27
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 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 $99
$110 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (741 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 $152
$169 total
includes taxes & fees
Apr 26 - Apr 27
Hyatt Place Kent Narrows & 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.
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Top landmarks in Chester

Chesapeake Exploration Center

Chesapeake Exploration Center is worth a visit, located 0.8 mi (1.4 km) from central Kent Narrows.
See properties

Learn more about Chester

The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.

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

Check out reviews of Chester hotels guests love

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Valet parking with a price,rooms of clean comfortable, staff was excellent, polite, courteous, no bar"
Moses 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Frequently asked questions

What accommodations do travelers recommend in Chester?
Guests like Hyatt Place Kent Narrows & Marina, Best Western Kent Narrows Inn and The Inn at Chesapeake Bay Beach Club.
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.