Search Cabin Rentals in Chestertown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is SAR 405
SAR 463 total
includes taxes & fees
1 Apr - 2 Apr
The Lodge at Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is SAR 372
SAR 596 total
includes taxes & fees
31 Mar - 1 Apr
First Floor Studio Apartment in Historic Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (892 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is SAR 449
SAR 498 total
includes taxes & fees
12 Apr - 13 Apr
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (432 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is SAR 304
SAR 337 total
includes taxes & fees
9 Apr - 10 Apr
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Dusty floor . Shower curtain didn’t close . Spiders on the ceiling "
United States
Evelyn
The price is SAR 255
SAR 283 total
includes taxes & fees
9 Apr - 10 Apr
Driftwood Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is SAR 447
SAR 608 total
includes taxes & fees
30 Mar - 31 Mar
Kent Island Resort

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is SAR 553
SAR 613 total
includes taxes & fees
22 Apr - 23 Apr
Haven Point Inn and Gallery

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (885 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is SAR 380
SAR 422 total
includes taxes & fees
30 Mar - 31 Mar
Quality Inn Grasonville near Kent Island

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (37 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is SAR 507
SAR 1,249 total
includes taxes & fees
30 Mar - 31 Mar
Large 2 bedroom house with private parking in a nice neighborhood

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is SAR 533
SAR 1,283 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (10 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is SAR 372
SAR 509 total
includes taxes & fees
30 Mar - 31 Mar
Secluded Tiny Pool House -Private Pool -Self Check in

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (322 reviews)
"room was clean breakfast good staff very friendly"
United States
Robin
The price is SAR 411
SAR 460 total
includes taxes & fees
5 Apr - 6 Apr
Fairfield Inn & Suites by Marriott Aberdeen

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is SAR 969
SAR 1,958 total
includes taxes & fees
30 Mar - 31 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is SAR 255
SAR 469 total
includes taxes & fees
31 Mar - 1 Apr
Guest Suite for up to 2 in a Victorian on the Chester River

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (91 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is SAR 681
SAR 777 total
includes taxes & fees
1 Apr - 2 Apr
Flag House Inn

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is SAR 450
SAR 1,153 total
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (357 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is SAR 366
SAR 410 total
includes taxes & fees
5 Apr - 6 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,002 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is SAR 296
SAR 329 total
includes taxes & fees
28 Apr - 29 Apr
Quality Inn Smyrna

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

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.6 out of 10, Exceptional, (10 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
The price is SAR 456
SAR 787 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (12 reviews)
"Very clean first off I would’ve ate off the floor. Honestly these people have to love what they do to deliver such a 5 star experience "
United States
Anonymous traveler
The price is SAR 1,005
SAR 2,162 total
includes taxes & fees
5 Apr - 6 Apr
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia