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5 Sept - 7 Sept
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Top 10 Chester hotels and places to stay

Red Roof Inn Annapolis
Standard Room, 2 Double Beds, Non Smoking | 1 bedroom, desk, iron/ironing board, free WiFi

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (381)
"I liked the landscaping, the greeting of the lobby staff upon check in, and 2 staff members in the lobby when checking out. The room was very nice and quiet. I am very pleased with this hotel. Thank you for making my stay great."
The price is £64
includes taxes & fees
2 Sept - 3 Sept
Red Roof Inn Annapolis
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (872)
"Great room for a great price... Very friendly staff, too."
The price is £92
includes taxes & fees
2 Sept - 3 Sept
Sonesta ES Suites Annapolis
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is £114
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1840)
"Great value and location. "
Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout curtains

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1023)
"Nice location. "
The price is £85
includes taxes & fees
7 Sept - 8 Sept
Country Inn & Suites by Radisson, Annapolis, MD
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (137)
"Liked everything my stay was wonderful will be back "
The price is £128
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites By Marriott Annapolis
SpringHill Suites by Marriott Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Clean room, Good breakfast and friendly staff."
The price is £96
includes taxes & fees
15 Sept - 16 Sept
SpringHill Suites by Marriott Annapolis
Econo Lodge Easton Route 50
Free continental breakfast

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (373)
"The staff was VERY nice"
The price is £66
includes taxes & fees
30 Sept - 1 Oct
Econo Lodge Easton Route 50
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1011)
"Very nice property new rooms "
The price is £70
includes taxes & fees
3 Sept - 4 Sept
Best Western Annapolis
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is £139
includes taxes & fees
2 Sept - 3 Sept
Flag House Inn
Hilton Garden Inn Annapolis Downtown
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1011)
"Clean well appointed rooms close to center of town. Very helpful staff. "
The price is £89
includes taxes & fees
14 Sept - 15 Sept
Hilton Garden Inn Annapolis Downtown
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (66)
"Good service and good options to enjoy the stays. "
The price is £171
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is £169
includes taxes & fees
4 Sept - 5 Sept
George Brooks House B&B
Quality Inn
Exterior

Quality Inn

2.5 star property
7.6 out of 10, Good, (778)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is £69
includes taxes & fees
1 Oct - 2 Oct
Quality Inn
TownePlace Suites by Marriott Annapolis
Exterior

TownePlace Suites by Marriott Annapolis

3.0 star property
8.8 out of 10, Excellent, (15)
"very clean, and quiet, we are very comfortable with our stay with TownePlace Suites by Marriott Annapolis. Staff were friendly and we have a great check in."
The price is £93
includes taxes & fees
7 Sept - 8 Sept
TownePlace Suites by Marriott Annapolis
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (493)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is £67
includes taxes & fees
9 Sept - 10 Sept
Village Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (618)
"Great location"
The price is £133
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina
Residence Inn By Marriott Annapolis
Property amenity

Residence Inn By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (45)
"It was close to the Stadium."
The price is £143
includes taxes & fees
2 Sept - 3 Sept
Residence Inn By Marriott Annapolis
Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (79)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
Hummingbird Inn
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is £128
includes taxes & fees
2 Sept - 3 Sept
Mariners Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Check out pet-friendly hotels in Chester

Waterfront House: Hot Tub, Fire Pit, & Views
Outdoor dining

Waterfront House: Hot Tub, Fire Pit, & Views

9.4 out of 10, Exceptional, (3)
The price is £521
includes taxes & fees
2 Sept - 3 Sept
Waterfront House: Hot Tub, Fire Pit, & Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chester

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

See all hotels in Chester
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

More cheap stays in Chester

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis, MD
The price is £70 per night from 3 Sept to 4 Sept
£70
3 Sept - 4 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where can I find the best nightlife in Chester?
Chester is a charming area with a laid-back atmosphere, but when it comes to nightlife, options are somewhat limited.

However, nearby Annapolis, just a short drive away, boasts a vibrant nightlife scene that's well worth the visit. In Annapolis, the historic downtown area features bustling bars and live music venues along West Street, where you can enjoy everything from casual pubs to upscale lounges.

For those who enjoy a lively waterfront experience, the area around Ego Alley is superb for sipping cocktails while watching boats glide by. If you're searching for a relaxed evening, consider heading to the local breweries or wine bars that often host events and tastings.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a Chester hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from £69 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.