Title: Best Chestertown, MD Lodge Rentals from $137 | Expedia.com

[Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

Next weekend

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chestertown lodges

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lodge at Great Oak Landing

[](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

Chestertown

7.8/10

Good

(77 reviews)

"Very nice rooms, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephania

$124 nightly

$137 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

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](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely. "

[](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg)

### Best Western Plus Hotel & Conference Center

6/10 Okay

"Breakfast had plenty of choices for the family. The pool was supposed to be heated and it was not the majority of the days, with ceiling tiles falling down."

[](https://expedia.com/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08_y.jpg)

### Hilton Garden Inn Baltimore/White Marsh

8/10 Good

"Breakfast, was delicious."

[](https://expedia.com/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg)

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

2/10 Terrible

"Hotel is nasty straight up hood"

[](https://expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information)

![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/5d79a398_y.jpg)

### Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent

"It was great!!! I would absolutely stay there again. Clean, friendly staff, comfy, quiet…"

[](https://expedia.com/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information)

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Clean"

[](https://expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/c6a165a6_y.jpg)

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

8/10 Good

"My Family and I enjoyed our stay here as well as the variety of breakfast options. Fell short of giving it an excellent review because we were initially given a room that seem to have mould on the bathroom ceiling, however, our room was changed once we complained and the new room was very clean. Will definitely recommend a stay here."

[](https://expedia.com/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information)

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

"A house problem means a one night local area stay. No issues with registration, good rate and clean room."

[](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information)

![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df_y.jpg)

### Courtyard by Marriott Baltimore Downtown/McHenry Row

8/10 Good

"The stay was great, staff was super helpful but they did not offer late check out because the room was booked via Hotels.com. "

[](https://expedia.com/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information)

## Find out more about Chestertown

## Chestertown Lodges information

| Number of reviews | 77       |
| ----------------- | -------- |
| Accommodation     | 1 Lodges |
| Lowest Price      | $137     |
| Highest Price     | $137     |

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