Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Apr 28 - Apr 29
Tomorrow
Apr 29 - Apr 30
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

Where to stay in Chester?

Reception
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
The price is $136
$185 total
includes taxes & fees
Apr 29 - Apr 30
Kent Island Resort
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,000 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 $108
$120 total
includes taxes & fees
May 4 - May 5
Best Western Kent Narrows Inn
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, (996 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 $130
$144 total
includes taxes & fees
May 26 - May 27
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (750 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 $179
$199 total
includes taxes & fees
Apr 29 - Apr 30
Hyatt Place Kent Narrows & Marina
Front of property - evening/night
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, (449 reviews)
Escape to this serene Chesapeake retreat featuring an outdoor pool and indulgent spa treatments. Just minutes from Northern Chesapeake Bay and Paul Reed Smith Guitars, the hotel offers a cafe, 24-hour fitness center, and attentive staff that guests consistently praise.
The price is $216
$265 total
includes taxes & fees
Apr 30 - May 1
The Inn at Chesapeake Bay Beach Club
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, (1,003 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 $155
$172 total
includes taxes & fees
May 25 - May 26
Hilton Garden Inn Kent Island Marina
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, (899 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
May 18 - May 19
Quality Inn Grasonville near Kent Island
Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 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 $200
$223 total
includes taxes & fees
May 5 - May 6
Inn at Huntingfield Creek
Lobby lounge
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
Warm B&B located steps from the Naval Academy with free breakfast featuring local cuisine. Enjoy free WiFi while exploring nearby attractions like John Smith House and Annapolis City Dock. Valet parking is also available.
The price is $227
$259 total
includes taxes & fees
May 3 - May 4
Flag House Inn
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
Immerse yourself in Annapolis at this luxury boutique hotel near the City Dock and John Smith House. Enjoy free breakfast featuring local cuisine each morning and complimentary WiFi throughout your stay while exploring Maryland's picturesque capital.
The price is $298
$340 total
includes taxes & fees
May 4 - May 5
134 Prince - Luxury Boutique Hotel
Exterior
Haven Point Inn and Gallery
Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is $155
$172 total
includes taxes & fees
Apr 29 - Apr 30
Haven Point Inn and Gallery
Meeting facility
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,850 reviews)
Nestled in the heart of Annapolis, this historic hotel offers easy access to the Naval Academy. Unwind in comfortable beds after exploring nearby attractions, or enjoy a drink at the bar. The helpful staff and clean rooms earn high praise from travelers.
The price is $159
$215 total
includes taxes & fees
May 25 - May 26
Historic Inns of Annapolis
Lobby
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,002 reviews)
Explore downtown Annapolis from this stylish Art Deco hotel with Kitchen on West St serving regional cuisine. The 24-hour fitness center, in-room refrigerators, and microwaves enhance your stay near Annapolis Civil Rights Plaque.
The price is $117
$133 total
includes taxes & fees
May 3 - May 4
Hilton Garden Inn Annapolis Downtown
Terrace/patio
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (198 reviews)
This Annapolis hotel offers easy access to Navy-Marine Corps Memorial Stadium and Civil Rights Plaque. Unwind at the bar after a workout, enjoy complimentary WiFi, and start your day with free breakfast. Just a 5-minute drive from the Naval Academy.
The price is $144
$164 total
includes taxes & fees
May 7 - May 8
Fairfield Inn & Suites By Marriott Annapolis
Property amenity
The Westin Annapolis
The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,003 reviews)
Experience tranquility at this Annapolis hotel with a full-service spa offering massages and facials. Swim in the indoor pool, work out at the 24-hour fitness center, and enjoy cocktails at the bar. Near Maryland Hall for Creative Arts.
The price is $179
$204 total
includes taxes & fees
May 3 - May 4
The Westin Annapolis
Terrace/patio
Residence Inn By Marriott Annapolis
Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (71 reviews)
Discover comfort at this Annapolis hotel, just 5 minutes from the U.S. Naval Academy. Start your day with a complimentary buffet breakfast before exploring nearby attractions like Navy-Marine Corps Memorial Stadium. Unwind with a drink at the bar after your adventures.
The price is $161
$184 total
includes taxes & fees
May 7 - May 8
Residence Inn By Marriott Annapolis
Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (924 reviews)
Wake up to shimmering harbor vistas at this waterfront gem steps from U.S. Naval Academy. After breakfast at Pussers Caribbean Grille, explore nearby Ego Alley or work out in the 24-hour fitness center while luxury yachts drift by.
The price is $229
$261 total
includes taxes & fees
May 10 - May 11
Annapolis Waterfront Hotel, Autograph Collection
View from property
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,005 reviews)
This quiet Annapolis hotel offers a peaceful atmosphere near shopping and dining options. Enjoy the 24-hour fitness center, comfortable beds, and friendly bar/lounge. Borrow free bicycles to explore nearby attractions while the helpful staff ensures a comfortable stay.
The price is $171
$195 total
includes taxes & fees
May 10 - May 11
Graduate by Hilton Annapolis
Dining
Best Western Annapolis
Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,005 reviews)
The price is $76
$86 total
includes taxes & fees
Apr 30 - May 1
Best Western Annapolis
Front of property
The Wildset
The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (434 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
May 5 - May 6
The Wildset
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.
View all properties

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
"This was an absolutely beautiful hotel, full of history and charm. The staff was super friendly and helpful also. I would absolutely stay here again."
Jennifer 3-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Frequently asked questions

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