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Best Resorts in Chester

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
$81 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn
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

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (862)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$85 nightly
The price is $94
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
$175 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1004)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
$71 nightly
The price is $81
Dec 28 - Dec 29
Total with taxes and fees
Best Western Annapolis
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
"Great place!"
United States
Tawnya
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
$109 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Easton
Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

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, (1003)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
$95 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
$120 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Knapps Narrows Marina & Inn
Front of property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
$105 nightly
The price is $116
Dec 24 - Dec 25
Total with taxes and fees
St Michaels Inn
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (841)
"Friendly staff, spotless room, great location. "
United States
Steven
$179 nightly
The price is $197
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Tidewater Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$179 nightly
The price is $195
Dec 14 - Dec 15
Total with taxes and fees
Kent Island Resort
Property amenity
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (165)
"Beautiful and very modern, breakfast was great"
United States
Dominic
$110 nightly
The price is $125
Dec 18 - Dec 19
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1001)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$83 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Best Western Kent Narrows Inn
Hypo-allergenic bedding, down comforters, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $84
Dec 22 - Dec 23
Total with taxes and fees
Hilton Garden Inn Annapolis
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
$149 nightly
The price is $170
Dec 28 - Dec 29
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
$110 nightly
The price is $122
Dec 21 - Dec 22
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (58)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
$144 nightly
The price is $160
Dec 15 - Dec 16
Total with taxes and fees
Inn at Huntingfield Creek
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1002)
"Excellent from check in to check out, highly recommend!"
United States
Eric
$106 nightly
The price is $121
Jan 11 - Jan 12, 2026
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1008)
"Great value for stay with breakfast included "
United States
Aisling
$79 nightly
The price is $90
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
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

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Chester

Chester Resorts information

Number of reviews
13,983
Accommodation
0 Resorts
Lowest Price
$81
Highest Price
$197

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 Love Point State Park are some places to visit nearby. Other attractions in the area include Sandy Point Beach and Queenstown Harbor Golf Club.
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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