A boat docked at a pier during twilight with a city skyline in the background.

Best Resorts in Chester

Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Two Adirondack chairs facing a calm body of water with a clear sky above.

1. 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, (1,000 reviews)
"Good hotel for the money and location."
United States
Marc
$110 nightly
The price is $122
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (841 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
$152 nightly
The price is $169
Oct 13 - Oct 14
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A patio with outdoor seating, overlooking a marina with boats.

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice 1 night stay"
United States
roney
$139 nightly
The price is $154
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

4. 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)
"Everyone was pleasant but the hotel was older and fairly expensive for the quality and look of the hotel. It was a motel at one point."
United States
Beth
$108 nightly
The price is $120
Oct 13 - Oct 14
Total with taxes and fees
Best Western Kent Narrows Inn
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

5. 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, (499 reviews)
"Great property super friendly, helpful staff."
United States
scott
$214 nightly
The price is $238
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (986 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
$96 nightly
The price is $107
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A large, two-story barn-style building with a covered front porch and a garage.

7. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (187 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
$154 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Kent Island Resort
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

8. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,038 reviews)
"Would stay again"
United States
Ashley
$131 nightly
The price is $150
Nov 1 - Nov 2
Total with taxes and fees
Historic Inns of Annapolis
A modern kitchen with dark cabinets, a white countertop, and a large window.

9. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
Cass-N-Reel Luxury Houseboat
An outdoor patio with tables, chairs, and a fire feature.

10. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (244 reviews)
"Nice hotel"
United States
Imola
$101 nightly
The price is $115
Oct 13 - Oct 14
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

11. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,235 reviews)
"My favorite place to stay in Annapolis"
United States
Michele
$90 nightly
The price is $103
Oct 12 - Oct 13
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A modern lobby with a seating area, a fireplace, and a bookshelf.

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"Loved everything about it but especially the staff was so friendly and accommodating!"
United Kingdom
petra
$106 nightly
The price is $121
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
A lighthouse with a white exterior, a balcony, and a metal roof.

13. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$248 nightly
The price is $266
Oct 7 - Oct 8
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

14. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,005 reviews)
"Great Hotel in a very central location"
United States
Mark
$147 nightly
The price is $167
Oct 26 - Oct 27
Total with taxes and fees
Graduate by Hilton Annapolis
Private kitchen

15. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (525 reviews)
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
United States
Keith
$83 nightly
The price is $95
Oct 12 - Oct 13
Total with taxes and fees
Village Inn Annapolis MD
A two-story building with a covered entrance and an American flag.

16. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,000 reviews)
"Great location close to downtown."
United States
Lynn
$99 nightly
The price is $109
Oct 7 - Oct 8
Total with taxes and fees
St Michaels Inn
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

17. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very good, (1,006 reviews)
"We stayed for 3 nights and we had a good experience."
Canada
Omer
$110 nightly
The price is $125
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

18. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,006 reviews)
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
United States
Silvia
$80 nightly
The price is $91
Oct 12 - Oct 13
Total with taxes and fees
Best Western Annapolis
A boat deck with a white bench and a view of a calm lake and distant trees.

19. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
$178 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
Inn at Huntingfield Creek
A modern lobby with a reception desk, seating area, and potted plants.

20. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,001 reviews)
"Nice place to stay friendly service"
United States
Glenn
$101 nightly
The price is $115
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn 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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Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Only complaint was no coffee or cups. And lightbulbs were out."
Perry 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Chester

Chester Resorts information

Number of reviews
9,084
Accommodation
0 Resorts
Lowest Price
$91
Highest Price
$266

Frequently asked questions

What can I expect from a resort vacation in Chester?
Expedia can help you browse resorts and other lodging options that have similar services and comforts. If you're having trouble finding a resort in Chester that works for you, you can use the search filters to look for hotels, or search for properties that offer amenities like swimming pools or all-inclusive rates. We make it simple to book great accommodations so you can move on to planning your trip itinerary.
What can I do in Chester?
If you're interested in local sights, Northern Chesapeake Bay, Matapeake State Park, and Eastern Neck National Wildlife Refuge are some places to visit nearby. Other attractions in the area include Sandy Point Beach and Queenstown Harbor Golf.
What's the seasonal 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.
What's the best way to get to and around Chester?
Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) away from the city center. Otherwise, look for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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