Chester Holiday Rentals from €97: Search Short-Term Rentals

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Holiday Rentals in Chester

Kitchen features oven, microwave, and dishwasher, along with a stainless steel sink and range hood.

"Nice big home with lots of room to be together"

Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "

Guests can access the marina from this dock, where several boats are moored.

"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "

Enjoy serene waterfront views and easy access to moorings and facilities.

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

Surround yourself with nature's serenity by the tranquil pool, complete with a soothing waterfall and lush greenery.

"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."

includes taxes & fees

5 Aug - 6 Aug

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a skylight above.

"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."

Boats docked at the marina, surrounded by calm waters and a picturesque view.

"Such a cute and unique place to stay. Very peaceful. "

"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. "

includes taxes & fees

5 Aug - 6 Aug

Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

Boats docked at the marina, surrounded by a serene grassy area and wooded surroundings.

"Awesome place!"

Overlooking the marina, the city skyline shines brightly.

"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."

includes taxes & fees

11 Aug - 12 Aug

Enjoy cooking in this well-equipped kitchen with a refrigerator, dark wood cabinetry, and a window with blinds.

"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 "

includes taxes & fees

5 Aug - 6 Aug

Kitchen area with Whirlpool microwave, stove, and spice rack.

"Great location, comfortable stay!!"

Enjoy cooking and dining in this well-equipped kitchen with appliances and a central island.

"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."

"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."

includes taxes & fees

18 Aug - 19 Aug

Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

"Nice weekend getaway!"

Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"

Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."

Stroll along the waterfront path to a historic bench, flanked by cannons, with serene views of the calm water and boats docked at the pier.

"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."

Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "

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Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Room is spacious, great for families"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Only complaint, the blackout drapes were almost two feet too short. I had to barricade the windows with couch cushions to block the lights entering at the floor level up to two feet high. It would’ve been nice to have a light switch to turn off lights on the terrace (never found one). That issue aside, bed comfort was decent with a variety of pillows. Bathroom was clean, room was comfy, spacious, had a great view (paid extra for it) and the hire is in a convenient location - within walking distance of some great seafood restaurants too. Hotel breakfast was what one might expect anywhere (meh) and it ended a little too early (9:30 am - should’ve ended at 10am)."

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"This is a beautiful hotel. We were given a room with a balcony. Gorgeous view of the bay. Lovely watching the sunset and then sunrise from the balcony. The room was clean. Bed comfortable. For the price would've been nice to have breakfast included but that's minor. "

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"The suite was very comfortable and open. The bed was very nice and comfortable. From the time we entered the main lobby we were made very welcoming. There's one restaurant at the hotel that provides you with a good variety of food. The bartender (Carlos) is from the area and recommended several places to check out to eat. He also makes a great Manhattan! The shuttle driver (Antwonne) is very helpful and points out places to check out. There are restaurants and shopping within walking distance from the hotel which is a bonus but I would recommend taking the shuttle into Annapolis and doing your shopping and eating. There is a pool at the hotel that is surprisingly large. The housekeeping staff were very helpful and respectful of our privacy. All in all this is a fantastic place to stay."

St Michaels Inn

10/10 Excellent

"Loved everything about this stay from the friendly staff, comfortable room and pristine pool. Enjoyed the continental breakfast each morning. Close to restaurants and shopping. A lovely outside area where we enjoyed the music of the mockingbirds. Anyone visiting St. Michaels should consider a stay at the St. Michael’s Inn."

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, apart-hotels, 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 favorite 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 depends 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 €97 per night. Entering your travel dates in the search wizard you might find 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chester is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 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 15 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.

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Holiday Rentals in Chester

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Holiday Rentals in Chester

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Floating 2 bed 2 bath condo stunning views of the bay

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Waterfront Oasis of Annapolis Star

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Chesapeake Houseboat Getaway on Kent Island, Maryland

Waterfront Getaway, Dock Your Boat & Play!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Relax on Kent Island in 3 Bedroom Home w/Waterview

Charming townhome with AC and WiFi in delightful Annapolis

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Bay views with kayaks, bikes, fire pit, crabbing and more

Edgewater/Mayo Gateaway w/ Hot Tub

The Heron's Nest at Atlantic Marina

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St. Michaels Waterfront Home

Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

DoubleTree by Hilton Hotel Annapolis

The Westin Annapolis

Hampton Inn & Suites Annapolis

St Michaels Inn

Country Inn & Suites by Radisson, Annapolis, MD

Holiday Inn Express & Suites Annapolis by IHG

Find out more about Chester

Frequently asked questions