Chester Hotels from €79 - Fully Refundable Options

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Go beyond your typical stay in Chester

Pet friendly

Pool

Apartment

Condo

Hot tub

Cottage

Waterpark

Family friendly

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Our top choices for Chester hotels

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

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

Grasonville

Betty

€118

includes taxes & fees

28 Sept - 29 Sept

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

€160

includes taxes & fees

8 Sept - 9 Sept

Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave

3. Best Western Kent Narrows Inn

Grasonville

chanel

€111

includes taxes & fees

28 Sept - 29 Sept

4. Hilton Garden Inn Kent Island Marina

Grasonville

roney

€161

includes taxes & fees

1 Sept - 2 Sept

5. Kent Island Resort

Stevensville

Margaret

€184

includes taxes & fees

14 Sept - 15 Sept

6. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

€96

includes taxes & fees

28 Sept - 29 Sept

7. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

€229

includes taxes & fees

28 Sept - 29 Sept

8. St Michaels Inn

St. Michaels

Karen

€85

includes taxes & fees

31 Aug - 1 Sept

9. Historic Inns of Annapolis

Historic District

Stephanie

€134

includes taxes & fees

29 Sept - 30 Sept

10. Crowne Plaza Annapolis by IHG

Annapolis

Heather

€95

includes taxes & fees

13 Sept - 14 Sept

42-inch LED TV with digital channels, TV

11. Hilton Garden Inn Annapolis Downtown

Annapolis

JOANA JENNIFER

€104

includes taxes & fees

7 Sept - 8 Sept

12. DoubleTree by Hilton Hotel Annapolis

Annapolis

Fabiana

€96

includes taxes & fees

27 Sept - 28 Sept

13. Best Western Annapolis

Annapolis

George

€79

includes taxes & fees

13 Sept - 14 Sept

Daily cooked-to-order breakfast for a fee

14. Hilton Garden Inn Annapolis

Annapolis

Glenn

€89

includes taxes & fees

27 Sept - 28 Sept

Room, 1 King Bed, Non Smoking, Fireplace

15. Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Leslie

€94

includes taxes & fees

27 Sept - 28 Sept

Desk, iron/ironing board (on request), free cots/infant beds, free WiFi

16. Village Inn Annapolis MD

Annapolis

Stephen

€82

includes taxes & fees

30 Aug - 31 Aug

17. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Gary

€137

includes taxes & fees

30 Aug - 31 Aug

Room, 1 King Bed, Non Smoking (Whirlpool)

18. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Frank

€96

includes taxes & fees

27 Sept - 28 Sept

19. Courtyard by Marriott Annapolis

Annapolis

Phyllis

€94

includes taxes & fees

7 Sept - 8 Sept

Pillow-top beds, in-room safe, desk, laptop workspace

20. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

€105

includes taxes & fees

13 Sept - 14 Sept

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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

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"Lovely room, clean, comfortable, well appointed & quiet. We’d be happy to stay longer in such a nice room! We asked for early check-in, & were told we’d be contacted when the room was ready, but there was no follow-up contact. Our morning shower had no hot water so we washed quickly! We knew there was ongoing work with the water supply but didn’t expect cold showers. When we reported the issue at the front desk, we were graciously offered breakfast at the on-site restaurant. So glad we accepted! Food (& service & view) were excellent. We didn’t consider the restaurant previously because there was no evidence of it aside from a sign on the door. A posted menu could help. It’s a long walk down a cold hallway and we totally would have not considered it as a breakfast option. Definitely recommend eating at the restaurant!"

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Great view of the water."

The Westin Annapolis

10/10 Excellent

"Walking distance from the historic main street."

The Tidewater Inn

10/10 Excellent

"We had a lovely stay at Tidewater Inn centrally located in downtown Easton within walking distance of charming shops and delicious restaurants. Our room was spacious and light filled. The bathroom was small but adequate. We ate at the restaurant in the hotel (Hunters Tavern) and had a fabulous meal. Will definitely be back."

Courtyard by Marriott Annapolis

10/10 Excellent

"Clean room and staff was very courteous."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

€79

13 Sept - 14 Sept

includes taxes & fees

7.8/10 Good! (1,002 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

€85

31 Aug - 1 Sept

includes taxes & fees

8/10 Very good! (1,012 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

€96

10 Sept - 11 Sept

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

€96

27 Sept - 28 Sept

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

€111

28 Sept - 29 Sept

includes taxes & fees

8/10 Very good! (1,004 reviews)

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

€118

28 Sept - 29 Sept

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.

What are some of the best holiday rentals that Chester has to offer?

Cute, Cozy 2-bedroom house near Annapolis with water access: This holiday home rental outside of Chester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. See all 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 Country Inn & Suites by Radisson, Annapolis, MD 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 Sandy Point Beach. You'll also find Queenstown Harbor Golf and Chesapeake Bay Bridge 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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Chester Hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

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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. Best Western Kent Narrows Inn

4. Hilton Garden Inn Kent Island Marina

5. Kent Island Resort

6. Quality Inn Grasonville near Kent Island

7. The Inn at Chesapeake Bay Beach Club

8. St Michaels Inn

9. Historic Inns of Annapolis

10. Crowne Plaza Annapolis by IHG

11. Hilton Garden Inn Annapolis Downtown

12. DoubleTree by Hilton Hotel Annapolis

13. Best Western Annapolis

14. Hilton Garden Inn Annapolis

15. Country Inn & Suites by Radisson, Annapolis, MD

16. Village Inn Annapolis MD

17. Fairfield Inn & Suites By Marriott Annapolis

18. Holiday Inn Express & Suites Annapolis by IHG

19. Courtyard by Marriott Annapolis

20. SpringHill Suites by Marriott Annapolis

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

St Michaels Inn

Hilton Garden Inn Annapolis Downtown

Holiday Inn Express Annapolis East-Kent Island by IHG

The Westin Annapolis

The Tidewater Inn

Courtyard by Marriott Annapolis

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Frequently asked questions

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