Photo by Patricia Knorr

Chester hotels from HK$591

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Our top choices for Chester hotels

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (675)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Centre and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.

"Great view, good ambiance all around"
United States
Dianne
The price is HK$856
HK$950 total
includes taxes & fees
25 Dec - 26 Dec
Hyatt Place Kent Narrows & Marina

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, (935)
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 on-site. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Centre after a quiet night's rest.

"It was very comfortable and clean"
United States
Maria
The price is HK$677
HK$751 total
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (430)
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 HK$1,284
HK$1,623 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Inn at Chesapeake Bay Beach Club

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 Centre and Queenstown Harbour 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 HK$661
HK$734 total
includes taxes & fees
28 Dec - 29 Dec
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, (1001)
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 Centre.

"Nice place "
United States
Tucker T
The price is HK$649
HK$720 total
includes taxes & fees
25 Dec - 26 Dec
Best Western Kent Narrows Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"Beautiful and peaceful property!"
United States
Jerry
The price is HK$1,114
HK$1,515 total
includes taxes & fees
22 Dec - 23 Dec
Kent Island Resort

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 centre for active travellers. Explore nearby Chesapeake Bay Environmental Centre, 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 HK$823
HK$913 total
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Kent Island Marina

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
Escape to this peaceful hotel offering free breakfast, WiFi, and parking. The seasonal outdoor pool provides refreshing relaxation, while the fitness centre 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 HK$628
HK$691 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
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 HK$1,393
HK$1,532 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn

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

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
Easton
9.6 out of 10, Exceptional, (366)
Start your day with complimentary breakfast at this Easton retreat, then swim in the indoor pool or exercise in the fitness centre. 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 HK$1,253
HK$1,378 total
includes taxes & fees
25 Dec - 26 Dec
Fairfield Inn & Suites by Marriott Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
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 centre. Business travellers 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 HK$932
HK$1,025 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hampton Inn Easton

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (120)
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 HK$1,595
HK$1,755 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Tilghman Island Inn

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
Enjoy scenic vistas from the rooftop terrace at this Easton B&B. Unwind with a massage, take a dip in the seasonal outdoor pool, or sip drinks at the bar. Free breakfast, WiFi and parking complement the serene garden setting near Saint Michaels Village.

" Beautiful property, wonderful staff, excellent food service."
United States
Seth
The price is HK$3,214
HK$3,535 total
includes taxes & fees
21 Dec - 22 Dec
The Oaks Waterfront

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 centre. 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.

"The kindest most sweetest checkin"
United States
Nicole
Hummingbird Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is HK$1,038
HK$1,485 total
includes taxes & fees
12 Jan - 13 Jan 2026
Wylder Tilghman Island

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (361)
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 HK$934
HK$1,027 total
includes taxes & fees
20 Dec - 21 Dec
Knapps Narrows Marina & Inn

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1004)
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 centre 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 HK$926
HK$1,018 total
includes taxes & fees
22 Dec - 23 Dec
Best Western Plus Easton Inn & Suites

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 centre. 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 HK$1,043
HK$1,147 total
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Inn Express Easton 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, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is HK$1,043
HK$1,189 total
includes taxes & fees
30 Dec - 31 Dec
Anchored Inn at Hidden Harbour 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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Stay near popular Chester attractions

Learn more about Chester

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

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

More cheap stays in Chester

Hotels in Chester with star-rating

Frequently asked questions

What's the best place to stay in Chester?
Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are DoubleTree by Hilton Hotel Annapolis and Annapolis Waterfront Hotel, Autograph Collection. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: This highly rated holiday home rental in Chester is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What are some accommodation options with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis and The Westin Annapolis are a couple of other choices that offer an on-site 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 accommodation options 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 Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge and Sandy Point Beach in the area. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

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