Photo by Patricia Knorr

Find hotels in Chester, MD from 2.135.181 ₫

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17 Dec - 18 Dec
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18 Dec - 19 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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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, (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 2.897.290 ₫
3.215.991 ₫ total
includes taxes & fees
24 Dec - 25 Dec
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, (934)
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 2.291.493 ₫
2.543.557 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
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, (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 4.345.935 ₫
5.494.052 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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 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 2.238.815 ₫
2.485.085 ₫ total
includes taxes & fees
21 Dec - 22 Dec
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, (1000)
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.
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is 2.197.199 ₫
2.438.891 ₫ total
includes taxes & fees
24 Dec - 25 Dec
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, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is 3.773.584 ₫
5.129.791 ₫ total
includes taxes & fees
24 Dec - 25 Dec
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, (1000)
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.
"Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening "
United States
Teresa
The price is 2.783.283 ₫
3.089.444 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Kent Island Marina
Exterior
Quality Inn

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 2.126.874 ₫
2.339.562 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn
Terrace/patio
The Tidewater 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 4.714.681 ₫
5.186.149 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn
Horse 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
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, (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 4.978.071 ₫
5.475.878 ₫ total
includes taxes & fees
18 Dec - 19 Dec
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, (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 2.865.156 ₫
3.151.724 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (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 5.920.200 ₫
6.512.220 ₫ total
includes taxes & fees
27 Dec - 28 Dec
The Tilghman Island Inn
Front of property
The Oaks Waterfront

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 10.869.487 ₫
11.956.436 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Oaks Waterfront
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 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
Seasonal outdoor pool
Wylder Tilghman Island

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 3.515.123 ₫
5.025.551 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Wylder Tilghman Island
Exterior
Knapps Narrows Marina & Inn

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 3.160.680 ₫
3.476.748 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Knapps Narrows Marina & Inn
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, (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 3.131.128 ₫
3.444.241 ₫ total
includes taxes & fees
18 Dec - 19 Dec
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 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 3.529.426 ₫
3.882.369 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
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, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is 3.532.060 ₫
4.026.706 ₫ total
includes taxes & fees
28 Dec - 29 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

Chesapeake Exploration Center

Learn about the events happening in 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

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is 1.872.966 ₫ per night from 28 Dec to 29 Dec
1.872.966 ₫
2.135.181 ₫ total
28 Dec - 29 Dec
includes taxes & fees
7.6/10 Good! (1,008 reviews)

Hotels in Chester with star rating

Frequently asked questions

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.