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Chester Holiday Rentals

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Holiday Rentals in Chester

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (126)
"This was a lovely property and the owners are very attentive and communicate well. The location is perfect for peaceful days/evenings enjoying the Bay, and it’s also a perfect launching spot for day trips to other attractions in the Eastern shore and Annapolis. I am very glad we stayed here. "
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (37)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (236)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (194)
"We had an amazing stay. The owner has literally thought of everything to make your stay the best experience! We had a range of ages in our family and everyone loved it. The beach was amazing."
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is AU$473
includes taxes & fees
28 Oct - 29 Oct
Waterfront Getaway, Dock Your Boat & Play!
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"Great location - very convenient to 50 and restaurants - very clean - greatly appreciated the water and potato chips"
Cass-N-Reel Luxury Houseboat
Charming townhome with AC and WiFi in delightful Annapolis
3.0 out of 10, (2)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is AU$131
includes taxes & fees
9 Nov - 10 Nov
Charming townhome with AC and WiFi in delightful Annapolis
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
The price is AU$454
includes taxes & fees
22 Oct - 23 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Luxury Waterfront Executive Family Home Annapolis with All Amenities
7.6 out of 10, Good, (4)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
Million Dollar View of the Chesapeake Bay
Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (28)
"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."
The price is AU$504
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (219)
"Very nice place, we will be visiting again!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is AU$394
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
The price is AU$937
includes taxes & fees
30 Oct - 31 Oct
Edgewater/Mayo Gateaway w/ Hot Tub
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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 AU$131 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chester offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Chester?

Choose from 14 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 Chesapeake Bay Environmental Center. Matapeake State Park and Love Point State Park 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.