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Find hotels in Chester, MD from CA $109

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Top 10 Chester hotels and places to stay

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1627)
"We had a pleasant stay at the Maryland Inn. It was a beautiful room and nicely appointed. The staff service was very good.My only disappointment was the towels were in need of upgrade ( old and worn), pillows were too firm (foam). Otherwise it was a very experience. "
The price is CA $187
CA $245 total
includes taxes & fees
Jul 1 - Jul 2
Historic Inns of Annapolis
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1041)
"The graduate hall/decor was interesting. Staffs were friendly. Place is clean and bed is comfortable. AC is strong but weirdly that it stops cooling (maybe trigger by motions?) during sleep. Plenty of parking onsite if needed(extra)."
The price is CA $254
CA $290 total
includes taxes & fees
Jul 1 - Jul 2
Graduate Annapolis
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1005)
"Liked free parking and convinient &near to shopping"
The price is CA $172
CA $196 total
includes taxes & fees
Jul 1 - Jul 2
Crowne Plaza Annapolis, an IHG Hotel
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Admiral Suites
2.5 star property
6.6 out of 10, (166)
"A nice experience"
The price is CA $109
CA $124 total
includes taxes & fees
Jun 23 - Jun 24
Admiral Suites
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1007)
"After having to leave my first reservation (different hotel). This was paradise. Courteous, helpful staff. Comfortable room and beds. "
The price is CA $162
CA $184 total
includes taxes & fees
Jul 1 - Jul 2
DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1009)
"Small quaint hotel, super nice front desk staff. "
The price is CA $138
CA $157 total
includes taxes & fees
Jun 17 - Jun 18
Country Inn & Suites by Radisson, Annapolis, MD
Homestyle Suites
2.5 star property
5.6 out of 10, (729)
"It was good"
The price is CA $123
CA $140 total
includes taxes & fees
Jun 9 - Jun 10
Homestyle Suites
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (865)
"We didn't have a hair dryer in the room and when I called the front desk, no one ever picked up. Also the parking charge in an open-air parking lot, in a setting that was nowhere near urban was disappointing. Overall the room was clean and quiet and it was great."
The price is CA $173
CA $197 total
includes taxes & fees
Jul 1 - Jul 2
Courtyard by Marriott Annapolis
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1008)
"Very nice area"
The price is CA $259
CA $295 total
includes taxes & fees
Jul 1 - Jul 2
The Westin Annapolis
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
8.8 out of 10, Excellent, (748)
"All of the buttons I selected."
The price is CA $114
CA $130 total
includes taxes & fees
Jul 4 - Jul 5
Microtel Inn & Suites by Wyndham Gambrills
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
9.0 out of 10, Wonderful, (713)
"I like everything about this property!"
The price is CA $327
CA $373 total
includes taxes & fees
Jun 16 - Jun 17
Annapolis Waterfront Hotel, Autograph Collection
Staybridge Suites Washington DC East - Largo, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (427)
"Second time staying there. Nice property with friendly staff. Easy check in, clean rooms. "
The price is CA $213
CA $241 total
includes taxes & fees
Jun 16 - Jun 17
Staybridge Suites Washington DC East - Largo, an IHG Hotel
Hilton Garden Inn Annapolis
3.0 star property
8.4 out of 10, Very good, (1008)
"Nice place"
The price is CA $154
CA $176 total
includes taxes & fees
Jun 17 - Jun 18
Hilton Garden Inn Annapolis
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (855)
"Great and clean "
The price is CA $190
CA $217 total
includes taxes & fees
Jun 30 - Jul 1
Hilton Garden Inn Annapolis Downtown
Comfort Inn Conference Center
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Everything was satisfactory. I will back again"
The price is CA $163
CA $184 total
includes taxes & fees
Jun 13 - Jun 14
Comfort Inn Conference Center
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (69)
"Quiet and beautiful. The staff was very professional and friendly. I felt like I was home. Looking forward to my next visit!!!"
The price is CA $317
CA $406 total
includes taxes & fees
Jun 10 - Jun 11
Kent Island Resort
SpringHill Suites by Marriott Annapolis
3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great stay"
The price is CA $162
CA $184 total
includes taxes & fees
Jun 16 - Jun 17
SpringHill Suites by Marriott Annapolis
Village Inn
2.0 star property
6.2 out of 10, (436)
"It’s extremely affordable and for the price the room was basic and clean. Parking is directly in front of your room and there wasn’t much around the motel, so it feels safe. The room had a smell which we think was cleaning products that was a little strong."
The price is CA $132
CA $150 total
includes taxes & fees
Jun 6 - Jun 7
Village Inn
Best Western Annapolis
2.5 star property
7.6 out of 10, Good, (1003)
"The room is showing some wear. It appears mold is starting to grow on bathroom ceiling. "
The price is CA $114
CA $131 total
includes taxes & fees
Jul 1 - Jul 2
Best Western Annapolis
Holiday Inn Express & Suites Annapolis, an IHG Hotel
2.5 star property
8.2 out of 10, Very good, (1002)
"Everything was fine about my stay. I was disappointed that I could not sign on to Netflix or prime on the tv. I was forced to watch shows on my iPad. For this reason I will probably not stay at your hotel again."
The price is CA $152
CA $173 total
includes taxes & fees
Jul 1 - Jul 2
Holiday Inn Express & Suites Annapolis, an IHG Hotel
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See all available properties in Chester
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.

More cheap stays in Chester

Hotels near Popular Chester Attractions

Chester Travel Info

Number of hotels
1,182
Highest price
CA $327
Lowest price
CA $109
Known attractions
Sandy Point State Park, Sandy Point Beach and Love Point State Park

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 traveler data. Other good choices for your visit to the area are Crowne Plaza Annapolis, an IHG Hotel and Graduate Annapolis. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental in Chester?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Chester vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind. 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?

Sonesta ES Suites Annapolis: Features buffet, a seasonal outdoor 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 Matapeake State Park, Chesapeake Bay Environmental Center, and Sandy Point Beach. You'll also find Queenstown Harbor Golf Club and Chesapeake Bay Bridge 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.

Recent Reviews in Chester
Expedia verified reviews