Title: Chester, MD Villas Rentals | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx3000440455)[Hotels in Chester](https://expedia.com/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d3000440455.Destination-Travel-Guides)

![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-06-19&endDate=2026-06-21&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 Chester

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/4e51f020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/21c5252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/e0e2d461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

[](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information)

Easton

7.6/10

Good

(846 reviews)

"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."

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

Jennifer

$85 nightly

$94 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Easton-Hotels-Quality-Inn.h11364.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/86e1ff48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/e01c273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/9f614534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/d898936b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Knapps Narrows Marina & Inn

[](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information)

Sherwood

9.4/10

Exceptional

(370 reviews)

"Clean room, helpful staff, nice breakfast, beautiful views, excellent location."

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

Denise

$90 nightly

$99 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/ec18bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking, Corner (with Sofabed) | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/9187439c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/3a599b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Easton Inn & Suites

[](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information)

Easton

9.2/10

Wonderful

(1,003 reviews)

"Nice friendly staff, clean room and lobby"

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

Joi

$119 nightly

$131 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/da259258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8d29fbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/814e7667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Anchored Inn at Hidden Harbour Marina

[](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information)

Deale

9.4/10

Exceptional

(476 reviews)

"Beautiful place to stay, we stay their one to two times a year."

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

Marjorie

$149 nightly

$170 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/76eda657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ee980eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/bc6750c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/e9e3336f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### St Michaels Inn

[](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

St. Michaels

8.2/10

Very Good

(1,000 reviews)

"Good value and close to downtown."

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

John

$82 nightly

$91 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Grasonville near Kent Island

[](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information)

Grasonville

7.8/10

Good

(875 reviews)

"Nice staff and rooms"

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

Walter

$84 nightly

$93 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.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)

![Business center](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.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)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.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

(1,007 reviews)

"Nice breakfast, cleanroom. Great location."

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

Wayne

$94 nightly

$104 total

Mar 1 - Mar 2

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/1000000/120000/117000/116919/36aae950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Annapolis East-Kent Island by IHG

[](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

Grasonville

9.2/10

Wonderful

(963 reviews)

"Clean room, I enjoy staying here every time I'm in the area"

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

Peter

$95 nightly

$106 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/18961763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Safari Suite | Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tidewater Inn

[](https://www.expedia.com/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information)

Easton

8.8/10

Excellent

(853 reviews)

"Friendly staff, spotless room, great location. "

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

Steven

$159 nightly

$175 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Easton-Hotels-The-Tidewater-Inn.h1105532.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/w1322h734x2y1-d973a563.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)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.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)

"Everything was clean and neat and welcoming "

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

Iriana J.

$144 nightly

$159 total

Feb 25 - Feb 26

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/103000000/102620000/102610200/102610148/c982427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/6e7f4df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/8af764c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wylder Tilghman Island

[](https://www.expedia.com/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information)

Tilghman

8.8/10

Excellent

(93 reviews)

"We were"

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

Guevara

$167 nightly

$184 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/w1504h992x0y8-f18eeee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/15cfa9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/d2bab96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/8260c7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Easton

[](https://www.expedia.com/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information)

Easton

9.0/10

Wonderful

(559 reviews)

"all excellent with kudos to staff and the breakfast cook."

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

JOSEPH

$110 nightly

$121 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6594eb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/1e71523a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free breakfast](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### George Brooks House B&B

[](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information)

St. Michaels

8.8/10

Excellent

(67 reviews)

"Gorgeous quaint historic house. Friendly owner, close to town "

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

Christopher

$169 nightly

$186 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/2360f1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/56e37930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Kent Island Marina

[](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

Grasonville

9.0/10

Wonderful

(1,001 reviews)

"Staff was friendly and rooms were clean. Beautiful area to visit. "

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

Amy

$114 nightly

$127 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/42ffb5fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/5cc5b3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterfront Double Queen First Level - Dog Friendly | View from room](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/0c190249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tilghman Island Inn

[](https://www.expedia.com/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information)

Tilghman

9.6/10

Exceptional

(123 reviews)

"Great room and water view! Staff is very friendly and welcoming. "

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

Nicole

$160 nightly

$176 total

Feb 26 - Feb 27

Total with taxes and fees

[](https://www.expedia.com/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/11cbce69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/742b0988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/d6387655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wildset

[](https://www.expedia.com/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information)

Downtown St. Michaels

9.8/10

Exceptional

(417 reviews)

"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "

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

Fred

$199 nightly

$219 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/St-Michaels-Hotels-The-Wildset.h64410566.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)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.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 great stay! The property has everything we needed and host was easy to communicate with "

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

Stephanie S.

$248 nightly

$263 total

Mar 2 - Mar 3

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/1000000/10000/2300/2264/d1ff59e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/716cdb36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/a352e55b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/662c7aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Easton by IHG

[](https://www.expedia.com/Easton-Hotels-Holiday-Inn-Express-Easton.h2264.Hotel-Information)

Easton

9.0/10

Wonderful

(597 reviews)

"Everything was great!"

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

HEATHER

$129 nightly

$142 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Easton-Hotels-Holiday-Inn-Express-Easton.h2264.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)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.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)

![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

(33 reviews)

"Great stay, would do it again."

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

Brandon D.

$261 nightly

$276 total

Mar 1 - Mar 2

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/c93a20ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Garden View | Garden view](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/b1a0ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/7a7c860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Perry Cabin

[](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information)

Downtown St. Michaels

9.6/10

Exceptional

(374 reviews)

"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "

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

Joseph

$371 nightly

$408 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.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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Houseboats

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE)

Condos

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Apartments

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Villas

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA)

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## Top Chester Hotel Reviews

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg)

### Graduate by Hilton Annapolis

10/10 Excellent

"Friendly, clean"

[](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Great services"

[](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Nice large room, clean, and temperature controls worked as expected. Front deck personnel were pleasant. Breakfast was good, with a variety of options."

[](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Great service!! Some hotel corporations forget this is the “hospitality business “. I arrived very late and the front desk personnel were so helpful "

[](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Perfect location. Clean room, nice amount of space, and friendly staff. "

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

![Fairfield Inn & Suites By Marriott Annapolis](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/ba30667e_y.jpg)

### Fairfield Inn & Suites By Marriott Annapolis

10/10 Excellent

"Great room, great hotel, very friendly and accommodating staff!"

[](https://expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"All great"

[](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Staff was awesome, shout out to Elena for all the help ."

[](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg)

### Candlewood Suites Annapolis by IHG

10/10 Excellent

"The room was clean and comfortable. The stove was easy to use but there were 2 burners. Great room and stay "

[](https://expedia.com/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

## Find out more about Chester

## Chester Villas information

| Number of reviews | 10,775   |
| ----------------- | -------- |
| Accommodation     | 3 Villas |
| Lowest Price      | $91      |
| Highest Price     | $408     |

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