Photo by Assya A

Find Shopping Hotels in Chestertown, MD from CA $86

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Shopping Hotels

Tonight
Sep 6 - Sep 7
Tomorrow
Sep 7 - Sep 8
Next weekend
Sep 12 - Sep 14
In two weeks
Sep 19 - Sep 21

Top Chestertown Shopping Hotels

Our top choices for Chestertown hotels with shopping nearby

Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1002)
"Nice clean hotel with very friendly staff"
The price is CA $141
CA $162 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Baltimore/White Marsh
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (17)
"The staff was great"
The price is CA $94
CA $173 total
includes taxes & fees
Sep 9 - Sep 10
Guest Suite for up to 2 in a Victorian on the Chester River
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is CA $242
CA $422 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Retreat with Private Dock and Beach
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (194)
"Great place close to eveything"
The price is CA $86
CA $283 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Fells Point Gem / In The Heart of Fells Point
Waterfront House: Hot Tub, Fire Pit, & Views
Outdoor dining

Waterfront House: Hot Tub, Fire Pit, & Views

9.4 out of 10, Exceptional, (3)
"Our stay was great! The convenience to nearby restaurants and stores worked really well for oir quick weekend trip! "
The price is CA $409
CA $761 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront House: Hot Tub, Fire Pit, & Views
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (79)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is CA $373
CA $684 total
includes taxes & fees
Sep 9 - Sep 10
Waterfront Oasis of Annapolis Star
Historic Row Home 1 Block from Gate 1 at USNA!
Interior

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
The price is CA $189
CA $984 total
includes taxes & fees
Sep 8 - Sep 9
Historic Row Home 1 Block from Gate 1 at USNA!
Charming Historic Row House in The Heart of Eastport's Horn Point
Dining

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is CA $415
CA $716 total
includes taxes & fees
Oct 6 - Oct 7
Charming Historic Row House in The Heart of Eastport's Horn Point
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (12)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is CA $1,244
CA $2,070 total
includes taxes & fees
Sep 8 - Sep 9
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
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.

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia