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Find Historic Hotels in Chestertown, MD

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Check availability on Chestertown Historic Hotels

Tonight
2 Sep - 3 Sep
Tomorrow
3 Sep - 4 Sep
This weekend
5 Sep - 7 Sep
Next weekend
12 Sep - 14 Sep

Top Chestertown Historic Hotels

Our top choices for Chestertown historic hotels

86 State Circle - Luxury Boutique Hotel
Exterior

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 899
AED 1,025 total
includes taxes & fees
7 Sep - 8 Sep
86 State Circle - Luxury Boutique Hotel
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1849)
"Excellent location, clean, friendly staff"
Historic Inns of 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 AED 604
AED 689 total
includes taxes & fees
3 Sep - 4 Sep
Flag House Inn
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel
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 AED 275
AED 806 total
includes taxes & fees
1 Oct - 2 Oct
Cozy Fells Point Gem / In The Heart of Fells Point
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is AED 1,322
AED 2,441 total
includes taxes & fees
3 Sep - 4 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is AED 275
AED 806 total
includes taxes & fees
1 Oct - 2 Oct
Hidden Fells Point Gem / Private Courtyard Patio
★ Midcentury Modern Getaway ★ Prime Location ★
3 bedrooms, iron/ironing board, travel crib, WiFi

★ Midcentury Modern Getaway ★ Prime Location ★

10.0 out of 10, Exceptional, (33)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
The price is AED 661
AED 2,043 total
includes taxes & fees
7 Sep - 8 Sep
★ Midcentury Modern Getaway ★ Prime Location ★
Freshly renovated 3-story home 1 block from USNA!
Fridge, microwave, oven, stovetop

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (37)
"Remodeled kitchen is well equipped and beautiful. "
Freshly renovated 3-story home 1 block from USNA!
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is AED 569
AED 1,319 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 2br home w/ parking in downtown 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.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location - easy to walk to most anywhere. Parking a bit expensive but overall experience was great "
Jason 2-night trip
Posted 1 day ago
Historic Inns of Annapolis
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Great everything. Staff, location. Need to go back when the pool is open!"
Cheryl 3-night trip
Posted 8 days ago
Sagamore Pendry Baltimore

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