Chester, MD

Travel Guide

Chester
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night from Jul 5 to Jul 6
$127 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$130 nightly
The price is $148 total per night from Jul 1 to Jul 2
$148 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,858 reviews)
"Bed had a wear to it where I rolled . Tub was rusted with grout having mold . The product container was suppose to hang on the wall but kept falling off and breaking the bottles so they did not work. Def not worth the price we paid. It was in a great vicinity."

Reviewed on Jun 20, 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night from Jul 5 to Jul 6
$125 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,002 reviews)
"It was our first time in the area so this hotel made the experience great all around. Everything was clean, the food was super good too! We ate breakfast two days in a row and ordered dinner and all meals were hot, fresh and delicious. The area where the hotel is at is convenient but it seems the ..."

Reviewed on Jun 20, 2026

Crowne Plaza Annapolis by IHG
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.
Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Annapolis MD
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Annapolis City Dock and Sandy Point State Park are located ...
10/10 Exceptional! (110 reviews)
"We had a wonderful three-night stay and couldn’t have been more pleased with both the property and the host. The cottage was exceptionally comfortable, relaxing, spotless, and very dog-friendly. It provided the perfect place to unwind while visiting family.We did experience a power outage during ..."

Reviewed on Jun 14, 2026

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.
Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (6 reviews)
"We had such a wonderful time staying at Grace Cottage. Lisa, the hostes, was very responsive and very, very kind. The cottage was right in the middle of all shopping and restaurants. It is beautifully decorated and is totally stocked with everything you would need. Thank you so much Lisa for making ..."

Reviewed on May 8, 2026

Grace Cottage, St Michaels Walk to everything!
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Annapolis MD
Stay at this apartment in Annapolis. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Westfield Annapolis Mall and Annapolis Mall Shopping ...
9.6/10 Exceptional! (91 reviews)
"Nathalie was excellent with communication. Property is as described and appears in photos. It is an apartment in a complex. As a few others have noted, there is a smell of cigarette. Sadly, I think it is neighbors smoking in their apartment. Especially in the morning. The apartment is really convenient ..."

Reviewed on Jun 2, 2026

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
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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