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Check prices for these dates

Next weekend
22 May - 24 May
In two weeks
29 May - 31 May

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Our top choices for Chester hotels

Exterior

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (869 reviews)
"We came in for the weekend and stayed for a family get together, had our 1 year old son. Property was quiet & the staff was nice. We had multiple family members staying so they put us all near each other which was a nice surprise and we all appreciated that."
United States
Kristina
The price is NZ$179
includes taxes & fees
19 May - 20 May
Quality Inn
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, (392 reviews)
"Love overnight staff"
United States
Ivvory
The price is NZ$153
includes taxes & fees
24 May - 25 May
Econo Lodge Easton Route 50
Lobby

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,001 reviews)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is NZ$205
includes taxes & fees
17 May - 18 May
Best Western Plus Easton Inn & Suites
Exterior

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (906 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is NZ$194
includes taxes & fees
19 May - 20 May
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"It is a nice Hotel."
United States
Dale
The price is NZ$214
includes taxes & fees
17 May - 18 May
Best Western Kent Narrows Inn
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
The price is NZ$222
includes taxes & fees
1 June - 2 June
St Michaels Inn
Lobby

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (372 reviews)
"Best bang for the buck you’re gonna get. The property was clean and well kept. The staff was great and it is located next to several restaurants. "
United States
ERIK
The price is NZ$268
includes taxes & fees
24 May - 25 May
Fairfield Inn & Suites by Marriott Easton
Bar (on property)

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (568 reviews)
"I have enjoyed Hampton Inns for years and this was no exception. The room and service were exceptional."
United States
Matthew
The price is NZ$241
includes taxes & fees
24 May - 25 May
Hampton Inn Easton
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, (604 reviews)
"Very friendly and helpful staff."
United States
Andrew
The price is NZ$281
includes taxes & fees
24 May - 25 May
Holiday Inn Express Easton by IHG
Lobby

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,008 reviews)
"Great location with good breakfast. 👍"
United States
David
The price is NZ$201
includes taxes & fees
7 June - 8 June
Country Inn & Suites by Radisson, Annapolis, MD
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,002 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is NZ$196
includes taxes & fees
25 May - 26 May
Hilton Garden Inn Annapolis
Property amenity

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Bar area very nice and relaxed."
United States
Stephanie
The price is NZ$238
includes taxes & fees
7 June - 8 June
Courtyard by Marriott Annapolis
Meeting facility

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (879 reviews)
"Enjoyable stay great location!"
United States
Michelle
The price is NZ$342
includes taxes & fees
16 June - 17 June
The Tidewater Inn
Free daily buffet breakfast

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,007 reviews)
"Wonderful place to stay!"
United States
Michele
The price is NZ$200
includes taxes & fees
26 May - 27 May
Sonesta ES Suites Annapolis
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,004 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is NZ$165
includes taxes & fees
24 May - 25 May
Best Western Annapolis
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,006 reviews)
"Great stay!"
United States
Jehane
The price is NZ$223
includes taxes & fees
31 May - 1 June
DoubleTree by Hilton Hotel Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,001 reviews)
"Very friendly and helpful staff. Room was very comfortable and well laid out. Would definitely stay again! "
United States
Cristi
The price is NZ$252
includes taxes & fees
31 May - 1 June
SpringHill Suites by Marriott Annapolis
Superior Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Bathroom

Red Roof Inn Annapolis

Red Roof Inn Annapolis
2.0 star property
Annapolis
7.2 out of 10, Good, (438 reviews)
"I always prefer to stay in red roof service is excellent neat and clean rooms "
United States
ZAHOOR
The price is NZ$144
includes taxes & fees
24 May - 25 May
Red Roof Inn Annapolis
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, (1,002 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is NZ$255
includes taxes & fees
7 June - 8 June
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,009 reviews)
"Breakfast was great -beds were comfortable -I would stay again "
United States
Lisa
The price is NZ$215
includes taxes & fees
24 May - 25 May
Crowne Plaza Annapolis by IHG
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
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"A very quaint and historic inn. This was my second stay at the Inns and the staff is very friendly and helpful. Our room was beautiful however, the bathroom needs a little work. Some new caulking and a little elbow grease in the bathtub would help."
Patrick 2-night trip
Posted 4 hours ago
Historic Inns of Annapolis

More cheap accommodation in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is NZ$165 per night from 24 May to 25 May
NZ$165
24 May - 25 May
includes taxes & fees
7.8/10 Good! (1,004 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 traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and Sonesta ES Suites Annapolis. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Sunset Bayview: sleeps 6: This highly rated holiday home rental in Chester is located on the waterfront, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Our travellers also rate Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! as a favourite home for rent in Chester. 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?
Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Courtyard by Marriott Annapolis and Crowne Plaza Annapolis by IHG 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 10 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 Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Eastern Neck National Wildlife Refuge 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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