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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Cabin Rentals in Chester

No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Great Hotel, Amazing location, very clean, everyone is friendly and helpful. Always recommend staying here if you are in Annapolis"
United States
Tatiana
The price is SAR 224
SAR 255 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Hotel Annapolis
Exterior
Quality Inn

Quality Inn

2.5 star property
Easton
7.6 out of 10, Good, (823)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is SAR 303
SAR 333 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"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
The price is SAR 405
SAR 578 total
includes taxes & fees
8 Dec - 9 Dec
Kent Island Resort
Meeting facility
The Tidewater Inn

The Tidewater Inn

3.0 star property
Easton
8.8 out of 10, Excellent, (840)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is SAR 634
SAR 698 total
includes taxes & fees
29 Dec - 30 Dec
The Tidewater Inn
Restaurant
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (89)
"Very relaxing stay."
United States
Anne
The price is SAR 450
SAR 661 total
includes taxes & fees
1 Jan - 2 January 2026
Wylder Tilghman Island
Exterior
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

3.0 star property
Easton
9.0 out of 10, Wonderful, (593)
"We only stayed one night but it was perfect. The room was very clean, the beds were comfortable, and the staff were very nice. "
United States
Nancy
The price is SAR 493
SAR 542 total
includes taxes & fees
1 Jan - 2 January 2026
Holiday Inn Express Easton by IHG
Exterior
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (858)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is SAR 319
SAR 354 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Exterior
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1013)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is SAR 297
SAR 339 total
includes taxes & fees
28 Dec - 29 Dec
Hilton Garden Inn Annapolis Downtown
Front of property
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (359)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is SAR 450
SAR 495 total
includes taxes & fees
7 Dec - 8 Dec
Knapps Narrows Marina & Inn
Exterior
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (668)
"Great view, good ambiance all around"
United States
Dianne
The price is SAR 436
SAR 484 total
includes taxes & fees
8 Dec - 9 Dec
Hyatt Place Kent Narrows & Marina
Exterior
Hampton Inn Easton

Hampton Inn Easton

2.5 star property
Easton
9.0 out of 10, Wonderful, (552)
"Super pet friendly, fresh cookies, and very clean rooms. "
United States
Megan
The price is SAR 456
SAR 502 total
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn Easton
View from property
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
"clean and comfy, friendly staff"
United States
Tamara
The price is SAR 388
SAR 427 total
includes taxes & fees
23 Dec - 24 Dec
St Michaels Inn
Exterior
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"I had a lovely stay."
United States
Kalynn
The price is SAR 243
SAR 277 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis
Exterior
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (162)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is SAR 443
SAR 505 total
includes taxes & fees
8 Dec - 9 Dec
Fairfield Inn & Suites By Marriott Annapolis
Exterior
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, (1000)
"Clean room, friendly staff"
United States
Jodi
The price is SAR 312
SAR 356 total
includes taxes & fees
28 Dec - 29 Dec
Country Inn & Suites by Radisson, Annapolis, MD
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, (929)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is SAR 297
SAR 330 total
includes taxes & fees
10 Dec - 11 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Property grounds
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"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
Inn at Huntingfield Creek
Front of property
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
The price is SAR 503
SAR 574 total
includes taxes & fees
30 Dec - 31 Dec
Anchored Inn at Hidden Harbour Marina
Exterior
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.2 out of 10, Very Good, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is SAR 315
SAR 349 total
includes taxes & fees
9 Dec - 10 Dec
Best Western Kent Narrows Inn
Exterior
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1915)
"Excellent hotel Really nice staff Love the valet guys "
United States
ben
Historic Inns of 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great Hotel, Amazing location, very clean, everyone is friendly and helpful. Always recommend staying here if you are in Annapolis"
Tatiana 2-night trip
Posted 21 hours ago
DoubleTree by Hilton Hotel Annapolis