Photo by Patricia Knorr

Chester Vacation Rentals

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Our top choices for Chester vacation rentals

9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is ¥15,504
¥24,876 total
includes taxes & fees
Jan 8 - Jan 9
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (43)
"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 ¥11,840
¥39,610 total
includes taxes & fees
Jan 8 - Jan 9
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 ¥30,868
¥70,238 total
includes taxes & fees
Jan 12 - Jan 13
HGTV quality, private guest suite, country getaway with hot tub & fire pit
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 ¥10,994
¥39,210 total
includes taxes & fees
Jan 8 - Jan 9
Charming Coastal/Country Home w/3 Acres & Sauna!
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 ¥12,685
¥51,000 total
includes taxes & fees
Jan 12 - Jan 13
Walk to Beach! King Bed & Free Beach Passes
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 ¥15,053
¥63,317 total
includes taxes & fees
Jan 11 - Jan 12
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (17)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is ¥18,449
¥44,415 total
includes taxes & fees
Jan 8 - Jan 9
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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 ¥39,153
¥65,573 total
includes taxes & fees
Jan 8 - Jan 9
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is ¥22,552
¥46,316 total
includes taxes & fees
Jan 8 - Jan 9
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥31,322
¥46,814 total
includes taxes & fees
Jan 8 - Jan 9
BAYSIDE BUNGALOW
9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
United States
Kedra B.
The price is ¥20,555
¥56,998 total
includes taxes & fees
Jan 14 - Jan 15
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is ¥36,745
¥88,130 total
includes taxes & fees
Jan 8 - Jan 9
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ¥32,418
¥64,808 total
includes taxes & fees
Jan 8 - Jan 9
Waterfront Oasis of Annapolis Star

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is ¥19,576
¥60,880 total
includes taxes & fees
Jan 8 - Jan 9
Luxury Pool Loft sleeps 4
The price is ¥338,278
¥489,366 total
includes taxes & fees
Jan 8 - Jan 9
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
The price is ¥24,666
¥66,504 total
includes taxes & fees
Jan 20 - Jan 21
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
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 ¥19,733
¥49,633 total
includes taxes & fees
Jan 8 - Jan 9
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
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 ¥23,805
¥88,197 total
includes taxes & fees
Jan 8 - Jan 9
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ¥23,648
¥86,590 total
includes taxes & fees
Feb 3 - Feb 4
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (5)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ¥26,467
¥82,840 total
includes taxes & fees
Jan 8 - Jan 9
Annapolis Retreat - 7 mins from downtown 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

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation rentals that Chester has to offer?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This vacation home rental near Chester is located on the beach and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Chester?

Choose from 10 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Chesapeake Bay Environmental Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.