Chester Holiday Rentals from €233: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Chester

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

"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "

"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."

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

includes taxes & fees

26 Aug - 27 Aug

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

"We really enjoyed our stay. Looking forward to staying again!"

includes taxes & fees

7 Sept - 8 Sept

"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

26 Aug - 27 Aug

"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"

"Nice weekend getaway!"

"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."

includes taxes & fees

8 Sept - 9 Sept

"Just perfect for a 4 night stay."

"Loved the location and the pristine condition of the house. "

"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "

"Awesome place!"

"Excellent location, Excellent property, Excellent owners!"

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

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

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

"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"

includes taxes & fees

9 Sept - 10 Sept

"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. "

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"It was a clean comfortable room. Didn’t like that you had to pay for parking when there was plenty of it and you couldn’t really walk anywhere that people would use this parking lot."

Hampton Inn & Suites Annapolis

10/10 Excellent

"It's poorly maintained. Baseboard in room coming off corner into the bathroom. Paint peeling off the bathroom door. Bathroom faucet was loose. The toilet seat was loose. Toilet runs on and off all the time. It was a very dark room, low wattage light bulbs and one of the lamps didn't work. There's a leak somewhere from the tub even when the shower curtain is closed and leaves a puddle. The Staff was very friendly though the lobby was old and dirty. We were supposed to stay there 6 days but left after the first night."

Courtyard by Marriott Annapolis

10/10 Excellent

"The staff was very friendly, our room and surrounding areas (hallway, courtyard, parking lot) were very clean. But somehow water would leak out of the shower and make a puddle on the floor. The carpet outside the tile in front of the closet would also get wet. We couldn't figure out how."

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 €233 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?

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Chester

Change your mind

Treat yourself

Be picky

Check prices for these dates

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

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

Waterfront Oasis of Annapolis Star

Floating 2 bed 2 bath condo stunning views of the bay

Cass-N-Reel Luxury Houseboat

Waterfront Getaway, Dock Your Boat & Play!

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

The Heron's Nest at Atlantic Marina

Large 2 bedroom house with private parking in a nice neighborhood

Chesapeake Houseboat Getaway on Kent Island, Maryland

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

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

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

Private Cottage on gated estate

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

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

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

St Michaels Inn

Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

Country Inn & Suites by Radisson, Annapolis, MD

Hampton Inn & Suites Annapolis

Courtyard by Marriott Annapolis

Historic Inns of Annapolis

Graduate by Hilton Annapolis

Find out more about Chester

Frequently asked questions