Chester Holiday Rentals

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Our top choices for Chester holiday rentals

9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is AU$226
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown
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 AU$385
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 AU$581
includes taxes & fees
6 Mar - 7 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$407
includes taxes & fees
5 Mar - 6 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$397
includes taxes & fees
8 Mar - 9 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
10.0 out of 10, Exceptional, (19 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 AU$460
includes taxes & fees
9 Mar - 10 Mar
Walk to Beach! King Bed & Free Beach Passes
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$450
includes taxes & fees
5 Mar - 6 Mar
Large 2 bedroom house with private parking in a nice neighborhood
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$664
includes taxes & fees
9 Mar - 10 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$565
includes taxes & fees
6 Mar - 7 Mar
Waterfront Oasis of Annapolis Star

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 AU$536
includes taxes & fees
11 Mar - 12 Mar
Luxury Pool Loft sleeps 4

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is AU$788
includes taxes & fees
9 Mar - 10 Mar
Neptune by the Water - Pet Friendly Fenced Yard

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$722
includes taxes & fees
9 Mar - 10 Mar
Cute bungalow blocks to Stadium
The price is AU$594
includes taxes & fees
9 Mar - 10 Mar
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
The price is AU$596
includes taxes & fees
10 Mar - 11 Mar
40' Bristol sailboat with spectacular views
9.8 out of 10, Exceptional, (7 reviews)
"Great place!"
United States
Chris A.
The price is AU$505
includes taxes & fees
11 Mar - 12 Mar
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$1,002
includes taxes & fees
5 Mar - 6 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$744
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 AU$710
includes taxes & fees
11 Mar - 12 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is AU$518
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$594
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: This highly rated holiday home rental in Chester is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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.