The Best Chestertown, MD Chalets

An aerial view of a town with a river, buildings, and surrounding greenery.

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Recommended hotels in Chestertown

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

$103 nightly

Sep 27 - Sep 28

Total with taxes and fees

2. Red Roof Inn & Suites Chestertown

Chestertown

Linda

$71 nightly

Sep 15 - Sep 16

Total with taxes and fees

Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, WiFi (free), bed sheets

3. The Lodge at Great Oak Landing

Chestertown

Lynda

$124 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Driftwood Inn

Chestertown

Vanesa

$64 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

$144 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

$319 nightly

Sep 7 - Sep 8

Total with taxes and fees

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

$270 nightly

Oct 5 - Oct 6

Total with taxes and fees

8. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

$271 nightly

Sep 7 - Sep 8

Total with taxes and fees

9. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

$463 nightly

Sep 8 - Sep 9

Total with taxes and fees

10. Haven Point Inn and Gallery

Rock Hall

Mary

$127 nightly

Oct 6 - Oct 7

Total with taxes and fees

11. Inn at Huntingfield Creek

Rock Hall

Christine

$200 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Millington

Riley B.

$118 nightly

Sep 10 - Sep 11

Total with taxes and fees

13. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Emily

$119 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

Rock Hall

lisa p.

$257 nightly

Sep 7 - Sep 8

Total with taxes and fees

15. BAYSIDE BUNGALOW

Rock Hall

Diane V.

$260 nightly

Sep 7 - Sep 8

Total with taxes and fees

16. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

Jennifer

$107 nightly

Sep 13 - Sep 14

Total with taxes and fees

17. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

Tatsiana

$90 nightly

Sep 20 - Sep 21

Total with taxes and fees

18. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

walter

$85 nightly

Sep 29 - Sep 30

Total with taxes and fees

19. Hilton Garden Inn Bel Air

Bel Air

michelle

$117 nightly

Sep 27 - Sep 28

Total with taxes and fees

20. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

$152 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent

"This hotel was actually better than I expected. Check-in was quick and easy. Lots of parking. My room on the 5th floor was spacious and super clean. The beds and pillows were great! The breakfast buffet was adequate. Overall, a good stay and I’d stay there again.,"

Red Roof Inn & Suites Chestertown

10/10 Excellent

"Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating."

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"Front desk pleasant and helpful, but… no accessible rooms available. Also, only non pet room available (even though reservations were made) was on 2nd floor and elevator out of service. Room itself was clean. Breakfast was good."

Best Western Plus Hotel & Conference Center

10/10 Excellent

"Multiple Elevators were out of service and had longer wait for available one to use. Buttons seemed to not work in that one elevator that was working and light kept going out for the floor I needed to be and kept stopping one floor below instead. But staff were so kind and friendly. Very helpful staff with information in area, shuttle information and very welcoming. I did enjoy staying and if coming to Baltimore again, I will choose to stay here again. Hope the elevator will be in good condition by the time I go back."

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Find out more about Chestertown

Chestertown Chalets information

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Recommended hotels in Chestertown

1. Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

3. The Lodge at Great Oak Landing

4. Driftwood Inn

5. First Floor Studio Apartment in Historic Chestertown

6. Newly restored apartment in the heart of Chestertown

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

8. Secluded Cottage in Middle of Chestertown

9. Wren Retweet- Country Estate in Center of C’Town

10. Haven Point Inn and Gallery

11. Inn at Huntingfield Creek

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

13. Holiday Inn Express Annapolis East-Kent Island by IHG

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

15. BAYSIDE BUNGALOW

16. SpringHill Suites Baltimore White Marsh/Middle River

17. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

18. Hampton Inn & Suites Edgewood/Aberdeen-South

19. Hilton Garden Inn Bel Air

20. Hyatt Place Kent Narrows & Marina

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Hampton Inn Baltimore/White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Red Roof Inn & Suites Chestertown

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Best Western Plus Hotel & Conference Center

The Lodge at Great Oak Landing

Find out more about Chestertown

Chestertown Chalets information

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