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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

Villas in Chester

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

Recommended hotels in Chester

Outdoor dining
Lansdowne Manor

Lansdowne Manor

Centreville
10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this beautiful old Manor house before and after my daughter‘s wedding. The rooms were great. The dinning room was breathtaking. We especially loved the kitchen area. Alex, the owner was very helpful and greeted us when we arrived. "
United States
Gary B.
The price is SAR 1,122
SAR 1,345 total
includes taxes & fees
15 Dec - 16 Dec
Lansdowne Manor
Exterior
Econo Lodge Easton Route 50

Econo Lodge Easton Route 50

2.5 star property
Easton
6.6 out of 10, (385)
"Staff was great"
United States
Andre
The price is SAR 304
SAR 334 total
includes taxes & fees
9 Dec - 10 Dec
Econo Lodge Easton Route 50
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
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
Exterior
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 star property
Easton
9.2 out of 10, Wonderful, (1007)
"Friendly check in and room was nice and updated "
United States
Gerald
The price is SAR 484
SAR 533 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Easton Inn & Suites
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
View from property
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

2.5 star property
Easton
9.6 out of 10, Exceptional, (364)
"Great hotel, very clean & quiet. "
United States
Janet
The price is SAR 683
SAR 751 total
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Easton
Porch
Hummingbird Inn

Hummingbird Inn

3.5 star property
Easton
10.0 out of 10, Exceptional, (86)
"The kindest most sweetest checkin"
United States
Nicole
Hummingbird Inn
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
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is SAR 740
SAR 1,671 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Exterior
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is SAR 372
SAR 596 total
includes taxes & fees
11 Dec - 12 Dec
First Floor Studio Apartment in Historic Chestertown
Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is SAR 1,550
SAR 1,705 total
includes taxes & fees
11 Dec - 12 Dec
The Oaks Waterfront
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
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is SAR 938
SAR 1,571 total
includes taxes & fees
15 Dec - 16 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Front of property
The Wildset

The Wildset

2.5 star property
St. Michaels
9.8 out of 10, Exceptional, (406)
"The breakfast bar had the same thing every day. It was all very fresh and healthy. The staff was always great. They did a lot to make you feel comfortable and enjoy your stay. Everything was very clean. "
United States
Adriana
The price is SAR 747
SAR 904 total
includes taxes & fees
11 Dec - 12 Dec
The Wildset
Deluxe Room | Premium bedding, down comforters, in-room safe, desk
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (370)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is SAR 1,354
SAR 1,638 total
includes taxes & fees
4 Dec - 5 Dec
Inn at Perry Cabin
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is SAR 751
SAR 826 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn
Front of property
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is SAR 638
SAR 702 total
includes taxes & fees
1 Jan - 2 January 2026
George Brooks House B&B
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
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is SAR 387
SAR 430 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
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 1 day ago
DoubleTree by Hilton Hotel Annapolis