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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Browse Select Chestertown Apartments

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (61)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (76)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is CA $372
CA $681 total
includes taxes & fees
Aug 19 - Aug 20
Waterfront Oasis of Annapolis Star
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (95)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is CA $136
CA $219 total
includes taxes & fees
Aug 14 - Aug 15
First Floor Studio Apartment in Historic Chestertown
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, (193)
"Great place close to eveything"
The price is CA $85
CA $281 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Fells Point Gem / In The Heart of Fells Point
Downtown furnished apartment - walking distance to restaurants
Interior

Downtown furnished apartment - walking distance to restaurants

10.0 out of 10, Exceptional, (5)
"The home is beautiful and exceptionally maintained! The management of the property is fantastic and they are lovely to work with. They thoughtfully had fresh fruit and some light & healthy munchies in the kitchen when I checked in. The history of the home is also quite interesting! I look forward to a return stay."
Downtown furnished apartment - walking distance to restaurants
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Marina

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

10.0 out of 10, Exceptional, (52)
"Everything about our stay was outstanding. Beautiful, just like the pictures show. We highly recommend this property."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Poe's Pad in Canton Quarters
Interior

Poe's Pad in Canton Quarters

9.0 out of 10, Wonderful, (2)
"Poe's Pad is perfect for us! It is conveniently located in super safe part of Baltimore. We've stayed here before and intend to do so many times again in the future!"
Poe's Pad in Canton Quarters
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (45)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is CA $162
CA $392 total
includes taxes & fees
Aug 14 - Aug 15
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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, (16)
"The staff was great"
The price is CA $84
CA $162 total
includes taxes & fees
Aug 21 - Aug 22
Guest Suite for up to 2 in a Victorian on the Chester River
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Interior

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (31)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Fridge, microwave, oven, stovetop

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

10.0 out of 10, Exceptional, (3)
"The house was clean and the beds were comfortable. "
The price is CA $186
CA $294 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop

Pristine Downtown 1-Bedroom Steps from State House

10.0 out of 10, Exceptional, (29)
"Our family loved having this as a short-term rental to visit our midshipman and give him the ability to relax off campus. The owners were communicative and amazing to work with for the entire 3 months! Would absolutely stay here again."
Pristine Downtown 1-Bedroom Steps from State House
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop

Cozy 1st Floor King George one bedroom apartment right across from USNA

10.0 out of 10, Exceptional, (31)
"We were thrilled to be able to return to this great apartment.It is very close to Gate 1 and the sofa bed has a great mattress on it!We hope to continue to return to this rental."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Spectacular Location: State Circle Apartment
Dining

Spectacular Location: State Circle Apartment

10.0 out of 10, Exceptional, (12)
"Great location around the corner from our Thanksgiving celebration. "
Spectacular Location: State Circle Apartment
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Property grounds

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

10.0 out of 10, Exceptional, (1)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Relaxation Haven on the Shore near Choptank River
Property grounds

Relaxation Haven on the Shore near Choptank River

9.2 out of 10, Wonderful, (7)
"The property is very quiet and peaceful! No issues at all! Helen was wonderful and very kind!"
Relaxation Haven on the Shore near Choptank River
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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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Wonderful historic hotel with clean rooms and friendly staff. Close to Naval Academy and waterfront shops and dining (5-minute walk, tops). Also close to Maryland State House (across the street) and several other historical sites. Loved our stay, with many future stays planned as we visit our new Midshipman in the months and years to come."
James 1-night trip
Posted 2 days ago
Historic Inns of Annapolis