Photo by Patricia Knorr

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Jul 9 - Jul 10
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Top 10 trending Chester hotels

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, (867)
"Great place"
The price is P6,304
P6,998 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (576)
"Great place to stay. "
The price is P8,576
P9,519 total
includes taxes & fees
Aug 4 - Aug 5
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (956)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is P8,626
P9,575 total
includes taxes & fees
Jul 20 - Jul 21
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very Good, (1000)
"I liked the spacious room and Jacuzzi. The free breakfast was good and staff was Amazing!"
The price is P5,140
P5,860 total
includes taxes & fees
Jul 28 - Jul 29
Hilton Garden Inn Annapolis
The Westin Annapolis
City view from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is P9,244
P10,538 total
includes taxes & fees
Jul 21 - Jul 22
The Westin Annapolis
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1003)
"Pleasant stay!!"
The price is P5,636
P6,425 total
includes taxes & fees
Jul 24 - Jul 25
Courtyard by Marriott Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (837)
"Front desk staff was very friendly and helpful."
The price is P13,138
P14,978 total
includes taxes & fees
Aug 4 - Aug 5
Annapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1000)
"Excellent hospitable staff made the stay even better!"
The price is P5,357
P6,107 total
includes taxes & fees
Aug 3 - Aug 4
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1795)
"Wonderful stay!"
Historic Inns of Annapolis
Holiday Inn Express & Suites Annapolis by IHG
1 bedroom, in-room safe, desk, laptop workspace

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1000)
"Decent property "
The price is P5,817
P6,631 total
includes taxes & fees
Jul 23 - Jul 24
Holiday Inn Express & Suites Annapolis by IHG
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (400)
"Staff was very polite and friendly. "
The price is P12,118
P14,885 total
includes taxes & fees
Jul 28 - Jul 29
The Inn at Chesapeake Bay Beach Club
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout drapes

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great location , perfect for my family stay."
The price is P5,701
P6,499 total
includes taxes & fees
Jul 27 - Jul 28
Country Inn & Suites by Radisson, Annapolis, MD
Hampton Inn & Suites Annapolis
Premium bedding, pillowtop beds, in-room safe, individually furnished

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very Good, (1004)
The price is P5,067
P5,777 total
includes taxes & fees
Jul 24 - Jul 25
Hampton Inn & Suites Annapolis
SpringHill Suites by Marriott Annapolis
Exterior

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great location , clean and friendly staff "
The price is P5,500
P6,270 total
includes taxes & fees
Jul 27 - Jul 28
SpringHill Suites by Marriott Annapolis
Wylder Tilghman Island
Living area

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (49)
"Excellent stay. Very relaxing and great facilities."
The price is P10,205
P13,493 total
includes taxes & fees
Jul 17 - Jul 18
Wylder Tilghman Island
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (104)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is P13,645
P17,383 total
includes taxes & fees
Jul 23 - Jul 24
Kent Island Resort
Hilton Garden Inn Annapolis Downtown
Living area

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1008)
"Really nice place to stay and enjoy Annapolis "
The price is P5,594
P6,377 total
includes taxes & fees
Aug 4 - Aug 5
Hilton Garden Inn Annapolis Downtown
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (104)
"Wonderful stay. "
The price is P7,158
P8,160 total
includes taxes & fees
Jul 21 - Jul 22
Fairfield Inn & Suites By Marriott Annapolis
Crowne Plaza Annapolis by IHG
Pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1004)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is P6,087
P6,939 total
includes taxes & fees
Jul 23 - Jul 24
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (834)
"Room was large & bed very comfortable. Very pleasant stay"
The price is P5,580
P6,361 total
includes taxes & fees
Jul 13 - Jul 14
Sonesta ES Suites Annapolis
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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Family-friendly hotels in Chester you'll enjoy

Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (516)
The price is P8,424
P9,266 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn Easton

Hotels with a spa in Chester may fit your trip

Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (76)
Hummingbird Inn

Check out pet-friendly hotels in Chester

Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (516)
The price is P8,424
P9,266 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn Easton
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

Frequently asked questions

What's the best place to stay in Chester?

Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are DoubleTree by Hilton Hotel Annapolis and Hilton Garden Inn Annapolis Downtown. 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What are some accommodations with pools in Chester?

Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Best Western Annapolis and Country Inn & Suites by Radisson, Annapolis, MD are a couple of other choices with an onsite 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 14 hotels and other accommodations to choose from. Find out more about Chester.

What is there to see in Chester?

Places to visit in the wider area include Matapeake State Park, Chesapeake Bay Environmental Center, and Love Point State Park. You'll also find Sandy Point Beach and Queenstown Harbor Golf Club in the area. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.