Chester Holiday Rentals from €174: Search Short-Term Rentals

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Our top choices for Chester holiday rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

includes taxes & fees

23 Nov - 24 Nov

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

includes taxes & fees

23 Nov - 24 Nov

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

3. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

includes taxes & fees

21 Nov - 22 Nov

A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

4. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

includes taxes & fees

24 Nov - 25 Nov

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

5. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

includes taxes & fees

24 Nov - 25 Nov

A sandy beach with a boat docked on the left and calm water.

6. Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

Guillaume P.

includes taxes & fees

22 Nov - 23 Nov

A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

7. Large 2 bedroom house with private parking in a nice neighborhood

Arnold

Linda B.

includes taxes & fees

16 Nov - 17 Nov

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

8. First Floor Studio Apartment in Historic Chestertown

Chestertown

Donna G.

A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

9. BAYSIDE BUNGALOW

Rock Hall

Nanci H.

A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.

10. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

A sandy beach with lounge chairs and a small pond.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

includes taxes & fees

16 Nov - 17 Nov

Aft deck with spiral staircase to the rooftop, sliding glass doors, and an unobstructed sunset view across the Magothy River from Ferry Point Marina.

12. Houseboat Suite for Two near Annapolis

Arnold

Anonymous traveller

A calm lake with boats docked, a sandy shore, and houses in the background.

13. Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

Diane D.

includes taxes & fees

16 Nov - 17 Nov

A white building with black shutters, a wooden door, and a number '53' on the wall.

14. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Bradford R.

includes taxes & fees

13 Dec - 14 Dec

A beach with a wooden fence and a pier in the distance.

15. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

Sam C.

includes taxes & fees

1 Dec - 2 Dec

A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

16. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

30 Nov - 1 Dec

A wooden dock extending into a calm body of water with boats docked at the end.

17. Cozy 2br home w/ parking in downtown Annapolis

Historic District

Nancy N.

includes taxes & fees

24 Nov - 25 Nov

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Cape Saint Claire

Jennifer H.

A spacious room with a large sliding glass door leading to a deck, a sofa, a chair, and a small table.

19. Bay Sunsets for Two • Rooftop Fire Pit

Pasadena

Charles W.

includes taxes & fees

19 Nov - 20 Nov

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

20. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

includes taxes & fees

14 Dec - 15 Dec

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Top Chester Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Positives included being close to the sites and Annapolis history, a very attentive hotel and valet parking staff with quick response to requests. Negatives included a noisy refrigerator, no microwave and a restaurant nearby playing loud music into the late evening. The only real choice was using valet parking and it was very expensive. Sometimes historic just means old. The rooms could use some updating."

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 €174 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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Chester is located near the beach, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chester?

Choose from 8 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 Eastern Neck National Wildlife Refuge 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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Check prices for these dates

Our top choices for Chester holiday rentals

1. Relax on Kent Island in 4 Bedroom Home w/Waterview

2. Charming Coastal/Country Home w/3 Acres & Sauna!

3. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!