Photo by Patricia Knorr

Chester Holiday Rentals

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Chester holiday rentals

Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$771
HK$1,238 total
includes taxes & fees
12 Jan - 13 Jan
First Floor Studio Apartment in Historic Chestertown
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"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 HK$497
HK$1,864 total
includes taxes & fees
11 Jan - 12 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, dishwasher, coffee/tea maker
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Holiday Home in Centreville

HGTV quality, private guest suite, country getaway with hot tub & fire pit
10.0 out of 10, Exceptional, (8 reviews)
"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 HK$1,536
HK$3,470 total
includes taxes & fees
19 Jan - 20 Jan
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Exterior
Charming Coastal/Country Home w/3 Acres & Sauna!

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"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 HK$497
HK$1,889 total
includes taxes & fees
11 Jan - 12 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17 reviews)
"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 HK$634
HK$2,541 total
includes taxes & fees
12 Jan - 13 Jan
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$909
HK$3,344 total
includes taxes & fees
11 Jan - 12 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17 reviews)
"Clean, comfortable and convenient! "
United States
Jill J.
The price is HK$918
HK$2,210 total
includes taxes & fees
11 Jan - 12 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Dining
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12 reviews)
"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 HK$1,948
HK$3,287 total
includes taxes & fees
12 Jan - 13 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,122
HK$2,296 total
includes taxes & fees
11 Jan - 12 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior detail
BAYSIDE BUNGALOW

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
BAYSIDE BUNGALOW
Terrace/patio
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Houseboat in Arnold

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the stay"
United States
Kedra B.
The price is HK$1,023
HK$2,836 total
includes taxes & fees
11 Jan - 12 Jan
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Dining
Charming Pet-Friendly Stay - Near Bay & Beaches.

Holiday Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is HK$1,828
HK$4,385 total
includes taxes & fees
11 Jan - 12 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,613
HK$3,224 total
includes taxes & fees
11 Jan - 12 Jan
Waterfront Oasis of Annapolis Star
Fridge, microwave, oven, stovetop
Luxury Pool Loft sleeps 4

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$974
HK$3,029 total
includes taxes & fees
11 Jan - 12 Jan
Luxury Pool Loft sleeps 4
Marina
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Houseboat in Edgewater

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
The price is HK$16,831
HK$24,179 total
includes taxes & fees
11 Jan - 12 Jan
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Property grounds
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Houseboat in Pasadena

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is HK$1,227
HK$3,300 total
includes taxes & fees
20 Jan - 21 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Interior
Large 2 bedroom house with private parking in a nice neighborhood

Holiday Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is HK$982
HK$2,469 total
includes taxes & fees
11 Jan - 12 Jan
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"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 HK$1,371
HK$4,628 total
includes taxes & fees
11 Jan - 12 Jan
Neptune by the Water - Pet Friendly Fenced Yard
TV, books, offices
Holly Hill Haven - Sleeps 10

Holiday Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,177
HK$4,246 total
includes taxes & fees
3 Feb - 4 Feb
Holly Hill Haven - Sleeps 10
Interior
Annapolis Retreat - 7 mins from downtown Annapolis!

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,317
HK$4,131 total
includes taxes & fees
11 Jan - 12 Jan
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"We use this property for business travel .Good clean property, nice location. Good breakfast and coffee. Reasonably priced (except parking fee)"
Michael 2-night trip
Posted 1 day ago
SpringHill Suites by Marriott Annapolis

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
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chester has to offer?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Chester?

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

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 wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips or small group gatherings.