Photo by Patricia Knorr

Find hotels in Chester, MD from ￥12,874

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Our top choices for Chester hotels

Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (691)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Center and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is ￥18,193
￥20,194 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (946)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available onsite. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Center after a quiet night's rest.
"It was very comfortable and clean"
United States
Maria
The price is ￥13,645
￥15,146 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

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, (433)
Located in Stevensville with easy access to Paul Reed Smith Guitars and Northern Chesapeake Bay, this hotel offers spa treatments, an outdoor pool, and a café. Enjoy free WiFi and parking while the helpful staff ensures a memorable stay.
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is ￥24,459
￥31,140 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Chesapeake Bay Beach Club
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

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links for easy exploration.
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥13,198
￥14,650 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Center.
"Nice place "
United States
Tucker T
The price is ￥13,084
￥14,523 total
includes taxes & fees
Jan 11 - Jan 12
Best Western Kent Narrows Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ￥20,067
￥27,782 total
includes taxes & fees
Jan 5 - Jan 6
Kent Island Resort
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness center for active travelers. Explore nearby Chesapeake Bay Environmental Center, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.
"Clean and friendly staff"
United States
Lisa
The price is ￥19,163
￥21,271 total
includes taxes & fees
Jan 8 - Jan 9
Hilton Garden Inn Kent Island Marina
Horseback riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
This elegant B&B features a seasonal outdoor pool and relaxing hot tub for unwinding after exploring nearby attractions. Free bike rentals invite local adventure while complimentary breakfast, WiFi, and parking enhance the luxury experience.
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (831)
Escape to this peaceful hotel offering free breakfast, WiFi, and parking. The seasonal outdoor pool provides refreshing relaxation, while the fitness center keeps your workout routine intact. Located near Talbot Massage and Easton Cycle and Sport, with exceptionally helpful staff.
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ￥13,331
￥14,664 total
includes taxes & fees
Jan 11 - Jan 12
Quality Inn
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (844)
Luxurious retreat featuring Hunters' Tavern serving regional fare for all meals. The full-service spa offers deep-tissue massages and body treatments, while the terrace and garden provide peaceful spaces. Located near Avalon Theatre with free WiFi and parking.
"Friendly staff, spotless room, great location. "
United States
Steven
The price is ￥28,056
￥30,862 total
includes taxes & fees
Feb 1 - Feb 2
The Tidewater Inn
View from property
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
Easton
9.6 out of 10, Exceptional, (368)
Start your day with complimentary breakfast at this Easton retreat, then swim in the indoor pool or exercise in the fitness center. The friendly staff, free parking, and in-room refrigerators create a convenient base near Talbot Massage.
"Great hotel, very clean & quiet. "
United States
Janet
The price is ￥25,197
￥27,716 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott Easton
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (557)
Wake up to a complimentary breakfast before exploring nearby Easton Cycle and Sport. This hotel offers an indoor pool for year-round swimming and a fitness center. Business travelers appreciate the free WiFi and parking with helpful staff.
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is ￥18,291
￥20,120 total
includes taxes & fees
Jan 29 - Jan 30
Hampton Inn Easton
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
This charming Tilghman inn offers stunning water views with convenient access to Tilghman Island Marina. Enjoy a complimentary breakfast before lounging by the seasonal outdoor pool or exploring the garden. The friendly staff and relaxing bar enhance your Eastern Shore getaway.
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ￥31,368
￥34,505 total
includes taxes & fees
Feb 1 - Feb 2
The Tilghman Island Inn
Porch
Hummingbird Inn

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (86)
Relax at this enchanting Victorian B&B with pampering spa massages and a 24-hour fitness center. Located near Easton Rail Depot and Avalon Theatre, guests enjoy in-room refrigerators, microwaves, and a rejuvenating hot tub, plus free breakfast, WiFi, and parking.
"This place is the cutest and they are the nicest people! The breakfast is delicious!!"
Canada
Chrystine
Hummingbird Inn
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.
"nice clean room staff very nice would stay again "
United States
mario
The price is ￥15,684
￥17,252 total
includes taxes & fees
Jan 5 - Jan 6
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (91)
"Very relaxing stay."
United States
Anne
The price is ￥16,986
￥25,585 total
includes taxes & fees
Jan 18 - Jan 19
Wylder Tilghman Island
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1003)
Start your day with a refreshing swim in the indoor pool before exploring nearby Talbot Massage and Easton Cycle and Sport. Free WiFi, parking, and fitness center enhance your stay at this business-friendly hotel where helpful staff ensure comfort.
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is ￥18,664
￥20,530 total
includes taxes & fees
Jan 5 - Jan 6
Best Western Plus Easton Inn & Suites
Free daily buffet breakfast
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (593)
Set near Talbot Massage and Easton Cycle and Sport, this welcoming hotel offers free breakfast, WiFi, and parking. Take a morning swim in the indoor pool, then visit the 24-hour fitness center. Guests consistently praise the property condition and helpful team.
"We only stayed one night but it was perfect. The room was very clean, the beds were comfortable, and the staff were very nice. "
United States
Nancy
The price is ￥21,801
￥23,981 total
includes taxes & fees
Jan 11 - Jan 12
Holiday Inn Express Easton by IHG
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (473)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ￥21,032
￥23,977 total
includes taxes & fees
Jan 6 - Jan 7
Anchored Inn at Hidden Harbour Marina
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (974)
Located minutes from U.S. Naval Academy, this peaceful hotel offers spacious suites and complimentary breakfast. The outdoor pool provides relaxation after exploring nearby shopping centers, while friendly staff ensure a comfortable stay close to major highways.
"Plenty of space for our group - nice layout! Nice showers & very clean! Breakfast was exceptional! Very pleased with the stay!!"
United States
Tammy
The price is ￥13,645
￥15,556 total
includes taxes & fees
Jan 28 - Jan 29
Sonesta ES 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.
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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
See properties

Learn more about Chester

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

See all hotels in Chester
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Amazing staff and breakfast was delicious. "
jennifer 1-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ￥11,292 per night from Jan 10 to Jan 11
￥11,292
￥12,874 total
Jan 10 - Jan 11
includes taxes & fees
7.6/10 Good! (1,005 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.: You might want to consider this vacation home rental near Chester, which is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What are some accommodations with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Annapolis, MD and The Westin Annapolis are a couple of other choices with an onsite pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer including the waterfront, seafood restaurants, and golf courses. In Chester, there are 11 hotels and other accommodations to choose from. Find out more about Chester.
What is there to see in Chester?
Places to visit in the wider area include Northern Chesapeake Bay, Matapeake State Park, and Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Eastern Neck National Wildlife Refuge in the area. Check out what more to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.

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