Photo by Patricia Knorr

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29 Jul - 30 Jul
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Top hotels and accommodation in Chester

St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Great spot to be close to town for a modest price. "
The price is NZ$204
includes taxes & fees
5 Aug - 6 Aug
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1014)
"Great hotel. No bar or restaurant onsite. If you stay there go to west end sports bar. Fantastic food and bartenders!!"
The price is NZ$169
includes taxes & fees
31 July - 1 Aug
Holiday Inn Express & Suites Annapolis by IHG
Quality Inn
Exterior

Quality Inn

2.5 star property
7.6 out of 10, Good, (754)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is NZ$169
includes taxes & fees
10 Aug - 11 Aug
Quality Inn
The Wildset
Premium Room

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (344)
"At check in we were notified our room was upgraded for our anniversary. The room was beautiful, right within walking distance to restaurants, shopping and even the water. The included breakfast was great, staff was sweet, and property was just amazing! We would love to return! "
The price is NZ$397
includes taxes & fees
13 Aug - 14 Aug
The Wildset
Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (794)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is NZ$186
includes taxes & fees
3 Aug - 4 Aug
Quality Inn
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is NZ$424
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Fairfield Inn & Suites by Marriott Easton
View from property

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (354)
"Very nice stay"
The price is NZ$271
includes taxes & fees
7 Aug - 8 Aug
Fairfield Inn & Suites by Marriott Easton
The Tidewater Inn
Terrace/patio

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (807)
"Very nice hotel, beautiful lobby areas."
The price is NZ$309
includes taxes & fees
10 Aug - 11 Aug
The Tidewater Inn
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is NZ$441
includes taxes & fees
30 July - 31 July
Inn at Haven Harbour
Best Western Plus Easton Inn & Suites
Lobby

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1013)
"Clean and great breakfast "
The price is NZ$236
includes taxes & fees
30 July - 31 July
Best Western Plus Easton Inn & Suites
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is NZ$271
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (56)
"Good service and good options to enjoy the stays. "
The price is NZ$386
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (337)
"This is a wonderful place "
The price is NZ$256
includes taxes & fees
30 July - 31 July
Knapps Narrows Marina & Inn
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1008)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is NZ$217
includes taxes & fees
5 Aug - 6 Aug
Best Western Kent Narrows Inn
SpringHill Suites by Marriott Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1018)
"Property was clean, newer hotel and convenient location."
The price is NZ$184
includes taxes & fees
3 Aug - 4 Aug
SpringHill Suites by Marriott Annapolis
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is NZ$286
includes taxes & fees
13 Aug - 14 Aug
Mariners Motel
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (522)
"Staff was very friendly"
The price is NZ$282
includes taxes & fees
7 Aug - 8 Aug
Hampton Inn Easton
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (122)
"The breakfast options were amazing."
The price is NZ$241
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites By Marriott Annapolis
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1017)
"Great hotel"
The price is NZ$148
includes taxes & fees
31 July - 1 Aug
Best Western Annapolis
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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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

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

10/10 Excellent
"The closers on the doors are so harsh, they rattle your ear drums. It is difficult to sit in the lobby and read with the doors banging all of the time. Even the checkin clerk has a door behind him that goes bang all of the time. Children under 10 would have a hard time even getting out of a room, in case of fire."
Larry 4-night trip
Posted 8 hours ago
Fairfield Inn & Suites By Marriott Annapolis

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 Graduate by Hilton Annapolis and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chester is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease 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. 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?

Country Inn & Suites by Radisson, Annapolis, MD: Features buffet, an indoor pool and free self parking. Best Western Annapolis and SpringHill Suites by Marriott 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 16 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 Matapeake State Park, Chesapeake Bay Environmental Center 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.