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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chester vacation homes

Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is AED 694
AED 1,316 total
includes taxes & fees
22 Dec - 23 Dec
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AED 377
AED 1,061 total
includes taxes & fees
21 Dec - 22 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AED 194
AED 825 total
includes taxes & fees
14 Dec - 15 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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

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 AED 724
AED 1,612 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AED 298
AED 1,161 total
includes taxes & fees
4 Jan - 5 January 2026
Walk to Beach! King Bed & Free Beach Passes
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.

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 AED 918
AED 1,514 total
includes taxes & fees
12 Dec - 13 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AED 826
AED 1,001 total
includes taxes & fees
23 Dec - 24 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AED 353
AED 1,477 total
includes taxes & fees
4 Jan - 5 January 2026
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is AED 862
AED 2,067 total
includes taxes & fees
15 Dec - 16 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is AED 657
AED 1,975 total
includes taxes & fees
16 Dec - 17 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,078 total
includes taxes & fees
11 Jan - 12 January 2026
BAYSIDE BUNGALOW
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is AED 479
AED 1,191 total
includes taxes & fees
14 Dec - 15 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AED 529
AED 1,566 total
includes taxes & fees
12 Dec - 13 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport
Pasadena
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
The price is AED 294
AED 582 total
includes taxes & fees
6 Jan - 7 January 2026
Modern New Suite Close to US Capital and BWI Airport
Outdoor pool
Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.8 out of 10, Excellent, (9)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is AED 400
AED 540 total
includes taxes & fees
14 Dec - 15 Dec
Secluded Tiny Pool House -Private Pool -Self Check in
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AED 536
AED 1,910 total
includes taxes & fees
14 Dec - 15 Dec
Cute bungalow blocks to Stadium
TV, books, offices
Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 617
AED 1,910 total
includes taxes & fees
5 Jan - 6 January 2026
Holly Hill Haven - Sleeps 10
Property grounds
New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!
Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AED 810
AED 1,847 total
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is AED 711
AED 1,752 total
includes taxes & fees
16 Dec - 17 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is AED 400
AED 1,281 total
includes taxes & fees
15 Dec - 16 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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"
stephen 3-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Annapolis