Title: 15 Best Cabins in Chestertown, MD - Cabins for Rent from $70 | 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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We are not like the others - we include taxes and fees

## Check prices for these dates

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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Chestertown

![Outdoor banquet area](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/e502e1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/021b413d.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)

![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)

### 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

$111 nightly

$123 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/5cb9165d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Studio Apartment in Historic Chestertown

[](https://www.expedia.com/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

Chestertown

9.6/10

Exceptional

(108 reviews)

"Every thing was great"

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

lesia k.

$144 nightly

$159 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/9028be2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Roof Inn & Suites Chestertown

[](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

Chestertown

7.2/10

Good

(433 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linette

$72 nightly

$80 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/5b16fcee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Chestertown

[](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

Chestertown

8.6/10

Excellent

(894 reviews)

"Best place to stay always "

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

Robert

$111 nightly

$123 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/fd47c937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/dc1f1cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/ff521238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/038e56e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly restored apartment in the heart of Chestertown

[](https://www.expedia.com/Chestertown-Hotels-Newly-Restored-Apartment-In-The-Heart-Of-Chestertown.h90876079.Hotel-Information)

Chestertown

9.8/10

Exceptional

(28 reviews)

"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""

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

Maggie D.

[](https://www.expedia.com/Chestertown-Hotels-Newly-Restored-Apartment-In-The-Heart-Of-Chestertown.h90876079.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/w353h265x3y3-b7952ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/7bc031db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Inn

[](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

Chestertown

5.2/10

(175 reviews)

"Rooms are clean, staf was helpful "

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

Daryl

$64 nightly

$70 total

May 1 - May 2

Total with taxes and fees

[](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/bb00a986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/1176437a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, Ensuite (Haven) | Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/89c7676f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Blackout drapes, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/5b38a1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Haven Point Inn and Gallery

[](https://www.expedia.com/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information)

Rock Hall

$140 nightly

$155 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Single Room, 1 King Bed | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kent Island Resort

[](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

Stevensville

9.2/10

Wonderful

(135 reviews)

"Beautiful hotel, nice staff"

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

Kim

$149 nightly

$162 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Flag House Inn

[](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information)

Historic District

9.2/10

Wonderful

(92 reviews)

"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "

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

Richard

$174 nightly

$199 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

[](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

Stevensville

9.8/10

Exceptional

(43 reviews)

"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"

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

Supriya V.

$243 nightly

$257 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w423h683x305y0-6862acf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w876h683x74y0-d9537acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

Millington

9.6/10

Exceptional

(20 reviews)

"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."

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

Cynthia C.

$118 nightly

$125 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/e1ce6cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/8628f41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Smyrna

[](https://www.expedia.com/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information)

Smyrna

7.6/10

Good

(1,001 reviews)

"My visit at the Hotel was amazing & peaceful."

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

Milton

$78 nightly

$86 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/762da084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

[](https://www.expedia.com/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

Exceptional

(38 reviews)

"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "

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

Traci L.

$288 nightly

$328 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/e9f923a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(35 reviews)

"Great stay, would do it again."

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

Brandon D.

$261 nightly

$277 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/b0ad5d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/6a6e65f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/7fa2b473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Fells Point Gem / Private Courtyard Patio

[](https://www.expedia.com/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

Fells Point

9.6/10

Exceptional

(94 reviews)

"Awesome place, great location"

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

Mark M.

$177 nightly

$204 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Kent Narrows Inn

[](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

Grasonville

8.0/10

Very Good

(1,001 reviews)

"Wonderful staff,Clean rooms and comfortable bed!!"

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

Evette

$99 nightly

$110 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/269a9c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/e058846a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/c3a4247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/w800h599x0y1-14614b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5-bedroom vacation home 5 minutes from historic Charlestown

[](https://www.expedia.com/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information)

Perryville

9.8/10

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

Mary D.

$497 nightly

$527 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/ed359310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/60127795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, towels](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/6b33d9f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/df579f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax Inn Smyrna

[](https://www.expedia.com/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.Hotel-Information)

Smyrna

8.0/10

Very Good

(94 reviews)

"Great location"

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

Patrick

$95 nightly

$102 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/d850b13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/b92b6259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/678460fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Aberdeen-APG

[](https://www.expedia.com/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information)

Aberdeen

9.0/10

Wonderful

(1,001 reviews)

"Near $95 and good place to stay"

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

Thandavarayan

$88 nightly

$99 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/5bf9cecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/052f9ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Tydings) | Premium bedding, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/727c3c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (O'Neill) | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vandiver Inn

[](https://www.expedia.com/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information)

Havre De Grace

9.4/10

Exceptional

(538 reviews)

"As always we loved our stay! Definitely will be coming back "

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

John

$123 nightly

$138 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.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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## Find vacation rentals that suit your style

Private vacation homes

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA)

Residences

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## Top Chestertown Hotel Reviews

![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

"all good"

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

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Delightful stay in an unbeatable location steps away from everything downtown Annapolis hasr to offer. Historic charm meets classy modern amenities in this historic hotel with beautifully furnished rooms, comfy beds, elegant bathrooms and attentive staff. Highly recommended!"

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

![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg)

### Comfort Inn & Suites Chestertown

8/10 Good

"The breakfast was as one would expect. Nothing unusual. I wish these hotels wouldn’t use so much plastic. Everything was clean. Chestertown is wonderful. Good restaurants. Much to see. The hotel is not fancy. Just a reliable place to be. Nothing unexpected. All good."

[](https://expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg)

### Home2 Suites by Hilton Baltimore/White Marsh

4/10 Poor

"I didn't eat at the property. "

[](https://expedia.com/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.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

4/10 Poor

"The hotel is worn. Our room wasn’t very clean; clump of hair(?) on the wall; sink area needed to be cleaned better. First floor hallway had odor of urine. Breakfast offerings were not kept up. (Empty coffee urns, no bacon). Not a good experience. "

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

6/10 Okay

"Average but ok for a business trip "

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

10/10 Excellent

"It was very nice. The hotel seems to have a cat who wanders the first floor, and that was very cute. We were treated very well."

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

10/10 Excellent

"Clean, spacious room. Quiet location. Decent breakfast. "

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

![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg)

### Best Western Kent Narrows Inn

8/10 Good

"Good to have a hot breakfast. Potatoes were slightly undercooked and we were there for 4 nights and very little variations in the menu. Would have been nice if there was a change in protein during our stay. The winner is the pool and hot tub. The first night we were there, we were able to get the steam room going, but after that, we couldn't get it to wok. Nevertheless, love that these were available especially on a cold night."

[](https://expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

## Find out more about Chestertown

## Chestertown Cabin Rentals information

| Number of reviews | 5,917           |
| ----------------- | --------------- |
| Accommodation     | 2 Cabin Rentals |
| Lowest Price      | $70             |
| Highest Price     | $527            |

## Frequently asked questions

### What are the best cabins near Chestertown?

### Are there cheap cabins in Chestertown?

### What are the best family cabins near Chestertown?

### What are the best river cabins near Chestertown?

### What are the best cabins with pools near Chestertown?

### What are some great Chestertown cabins?

### What are the best weekend cabin rentals in Chestertown?

### Can I find log cabins in Chestertown?

### What are the highest-rated cabins in Chestertown?

### What are the top things to see and do in Chestertown?

### Why should I book a cabin in Chestertown?

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