Chester Holiday Rentals, Maryland: Private House Rentals

A coastal town with a marina, a bridge, and a highway.

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Our top choices for Chester hotels

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A modern food court with a central island, various food stations, and a yogurt display.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

฿3,692

฿4,099 total

includes taxes & fees

25 Oct - 26 Oct

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

2. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

฿5,102

฿5,663 total

includes taxes & fees

25 Oct - 26 Oct

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

3. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

฿6,861

฿8,471 total

includes taxes & fees

2 Nov - 3 Nov

A patio with outdoor seating, overlooking a marina with boats.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

4. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

฿4,661

฿5,173 total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

A reception desk with a clock, framed pictures, and a sign for express checkout.

A restaurant with a counter, seating area, and a clock on the wall.

An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

5. Best Western Kent Narrows Inn

Grasonville

Wesley

฿3,017

฿3,349 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

A spacious lobby with a staircase, a reception desk, and a dining area.

6. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

฿3,032

฿3,365 total

includes taxes & fees

8 Nov - 9 Nov

A large, two-story barn-style building with a covered front porch and a garage.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A large, two-story white house with a porch and multiple windows.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

7. Kent Island Resort

Stevensville

Bethany

฿4,063

฿5,618 total

includes taxes & fees

28 Oct - 29 Oct

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

A historic brick building with a red roof, multiple windows, and a central staircase.

8. Historic Inns of Annapolis

Historic District

Ashley

฿2,876

฿4,427 total

includes taxes & fees

9 Nov - 10 Nov

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

฿3,558

฿4,056 total

includes taxes & fees

18 Oct - 19 Oct

A balcony with a table set for two, overlooking a marina with boats.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

A waterfront area with boats docked, a clear sky, and buildings in the background.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

10. Annapolis Waterfront Hotel, Autograph Collection

Historic District

฿7,492

฿8,541 total

includes taxes & fees

2 Nov - 3 Nov

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A buffet with various food items, including omelets and baked goods, in stainless steel containers.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

A microwave, a coffee maker, and a refrigerator in a kitchen area.

11. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

฿3,390

฿3,865 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

A hotel pool area with two pools, chairs, and a sunshade.

A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

12. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

฿3,994

฿4,554 total

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

13. The Westin Annapolis

Annapolis

Bobbi

฿6,693

฿7,630 total

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

14. Crowne Plaza Annapolis by IHG

Annapolis

Jose

฿3,599

฿4,102 total

includes taxes & fees

11 Nov - 12 Nov

15. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

฿3,551

฿4,048 total

includes taxes & fees

10 Nov - 11 Nov

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

A hotel with a covered entrance, multiple floors, and a parking lot.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

16. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

฿4,537

฿4,990 total

includes taxes & fees

1 Nov - 2 Nov

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

17. Graduate by Hilton Annapolis

Annapolis

Mark

฿4,937

฿5,628 total

includes taxes & fees

26 Oct - 27 Oct

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

18. Best Western Plus Easton Inn & Suites

Easton

Donna

฿4,330

฿4,763 total

includes taxes & fees

18 Oct - 19 Oct

A room with a view of a wooden deck and a gazebo by the water.

A hotel room with a large bed, a chair, a desk, and a television.

A golf course with a water hazard and surrounding trees.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

19. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

฿17,824

฿19,606 total

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a porch, a front door, and a small garden area.

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

20. The Wildset

Downtown St. Michaels

Sarah

฿7,687

฿9,295 total

includes taxes & fees

3 Nov - 4 Nov

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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

See properties

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester

Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room. Great breakfast."

Best Western Annapolis

8/10 Good

"Noisy balcony"

Historic Inns of Annapolis

10/10 Excellent

"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"all good. Very good when it comes to parking during a boat show."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"We stay here frequently. The best hotel in a great location."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Sonesta ES Suites Annapolis

10/10 Excellent

"Shalinda was the most welcoming front desk staff i have ever encountered."

More cheap stays in Chester

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,689

฿2,958 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,000 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,659

฿3,031 total

28 Oct - 29 Oct

includes taxes & fees

7.8/10 Good! (1,008 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,017

฿3,349 total

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (1,000 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

฿3,275

฿3,734 total

4 Nov - 5 Nov

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,390

฿3,865 total

9 Nov - 10 Nov

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

฿4,330

฿4,763 total

21 Oct - 22 Oct

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! You'll find that most hotel bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What are some accommodation options with pools in Chester?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. St Michaels Inn and Sonesta ES Suites Annapolis are a couple of other choices that offer an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfront, seafood restaurants and golf courses. In Chester, there are 9 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

Places to visit in the wider area include Northern Chesapeake Bay, Matapeake State Park and Eastern Neck National Wildlife Refuge. You'll also find Sandy Point Beach and Queenstown Harbor Golf in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

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Find hotels in Chester, MD from ฿2,958

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

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Our top choices for Chester hotels

1. Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Place Kent Narrows & Marina

3. The Inn at Chesapeake Bay Beach Club

4. Hilton Garden Inn Kent Island Marina

5. Best Western Kent Narrows Inn

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. Historic Inns of Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. Annapolis Waterfront Hotel, Autograph Collection

11. Holiday Inn Express & Suites Annapolis by IHG

12. SpringHill Suites by Marriott Annapolis

13. The Westin Annapolis

14. Crowne Plaza Annapolis by IHG

15. Hilton Garden Inn Annapolis Downtown

16. Fairfield Inn & Suites by Marriott Easton

17. Graduate by Hilton Annapolis

18. Best Western Plus Easton Inn & Suites

19. Inn at Perry Cabin

20. The Wildset

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

Best Western Annapolis

Historic Inns of Annapolis

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

The Inn at Chesapeake Bay Beach Club

Hyatt Place Kent Narrows & Marina

St Michaels Inn

Sonesta ES Suites Annapolis

More cheap stays in Chester

St Michaels Inn

Best Western Annapolis

Best Western Kent Narrows Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Plus Easton Inn & Suites

Frequently asked questions

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