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Top cities in Kent County
Chestertown
Check prices for these dates
Our top choices for Kent County hotels
1. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
8.0 out of 10, Very good, (131 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
William
The price is CA $154
CA $176 total
includes taxes & fees
Nov 17 - Nov 18
2. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
John
The price is CA $138
CA $153 total
includes taxes & fees
Dec 13 - Dec 14
3. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (515 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed.
The room needs up dating since damage area on ceiling and corner location rug worn spot.
I felt safe as a solo, could check in late and close to historic Chestertown.
I would come again."
Regina
The price is CA $103
CA $114 total
includes taxes & fees
Nov 22 - Nov 23
4. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The offsite property was perfect for my husband and I to enjoy the town and walk everywhere! Dinner at Waterman’s was a 12 minute walk, and drinks at the brewery was less then a minute walk."
Kat
The price is CA $243
CA $270 total
includes taxes & fees
Nov 17 - Nov 18
5. Driftwood Inn
Driftwood InnChestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
Kathy
The price is CA $91
CA $101 total
includes taxes & fees
Nov 16 - Nov 17
6. Inn at Haven Harbour
Inn at Haven HarbourRock Hall
7.8 out of 10, Good, (6 reviews)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon.
The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
Gloria
7. Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
9.6 out of 10, Exceptional, (20 reviews)
"We enjoyed our stay and would go back again."
Linda
8. 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 RiverMillington
9.8 out of 10, Exceptional, (34 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
Quinton
The price is CA $97
CA $166 total
includes taxes & fees
Nov 18 - Nov 19
9. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Great hosts… come to Rock Hall every year and found this cute cottage…will def come here every year. Great place"
Nanci H.
The price is CA $285
CA $429 total
includes taxes & fees
Nov 16 - Nov 17
10. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!Rock Hall
10.0 out of 10, Exceptional, (36 reviews)
"Great property! Great accommodations! Wonderful host"
lisa p.
The price is CA $191
CA $418 total
includes taxes & fees
Nov 21 - Nov 22
11. Life is better at the RIVER!--Cozy waterfront cottage
Life is better at the RIVER!--Cozy waterfront cottageGalena
10.0 out of 10, Exceptional, (123 reviews)
"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."
Katie S.
12. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.6 out of 10, Exceptional, (135 reviews)
"Easy to find and good parking. Nice quiet neighborhood. Has refrigerator and microwave. Excellent hot water. Thanks"
Donna G.
The price is CA $141
CA $215 total
includes taxes & fees
Nov 16 - Nov 17
13. Serene Waterfront Cottage with dock and gorgeous views.
Serene Waterfront Cottage with dock and gorgeous views.Rock Hall
9.6 out of 10, Exceptional, (43 reviews)
"This was a very serene and relaxing property to stay at. Loved that our dog was welcome here. Tons of things to do close by and great places to eat…our favorite was The Little Lemon Leaf Diner. The National Wildlife Refuge was also awesome to visit and kayak, we brought our own. Lots of kayaking opportunities right off the property as well. Rock Hall is a quaint little town and people are very friendly."
Amy F.
14. Waterfront! Private Dock, Boat Tie-Up & Near Town
Waterfront! Private Dock, Boat Tie-Up & Near TownRock Hall
9.6 out of 10, Exceptional, (9 reviews)
"A beautiful spot."
Laura S.
15. Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!Rock Hall
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful, quiet, very charming. Was the perfect little get away we were looking for "
Stephen G.
16. Grays Inn Creek Waterfront Pvt Dock Kayaks & View
Grays Inn Creek Waterfront Pvt Dock Kayaks & ViewRock Hall
10.0 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay. There was plenty of room for our large group to eat and play."
Eileen P.
17. Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of ChestertownChestertown
10.0 out of 10, Exceptional, (35 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
Susan A.
The price is CA $321
CA $480 total
includes taxes & fees
Nov 16 - Nov 17
18. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Cozy Family Friendly 1 story 3-bedroom house in charming BettertonBetterton
The price is CA $256
CA $489 total
includes taxes & fees
Nov 17 - Nov 18
19. Knot's Landing, spacious Apt. downtown Rock Hall
Knot's Landing, spacious Apt. downtown Rock HallRock Hall
9.6 out of 10, Exceptional, (16 reviews)
"Loved the location and historical aspects of the apartment! Would have liked more towels/washcloths."
Jean T.
20. Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront DiningRock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Great location right on the triathlon route. Super charming town that was fun to bike with kids. Hosts left a great PDF with lots of suggestions for fun activities,"
Chantal C.
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.
Compare top hotels in Kent County
The Lodge at Great Oak LandingChestertown | Comfort Inn & Suites ChestertownChestertown | Red Roof Inn & Suites ChestertownChestertown | Inn at Huntingfield CreekRock Hall | Driftwood InnChestertown |
|---|---|---|---|---|
8.0 Very good 131 reviews | 8.6 Excellent 1,000 reviews | 7.2 Good 515 reviews | 10.0 Exceptional 74 reviews | 5.4 183 reviews |
The price is CA $154 CA $176 total includes taxes & fees Nov 17 - Nov 18 | The price is CA $138 CA $153 total includes taxes & fees Dec 13 - Dec 14 | The price is CA $103 CA $114 total includes taxes & fees Nov 22 - Nov 23 | The price is CA $243 CA $270 total includes taxes & fees Nov 17 - Nov 18 | The price is CA $91 CA $101 total includes taxes & fees Nov 16 - Nov 17 |
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Top Kent County Hotel Reviews
The Wildset
The WildsetDowntown St. Michaels
10/10 Excellent
Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Mairi
