A coastal town with a marina, a bridge, and a highway.

2 Stars Hotels in Chester, Maryland from CA $120

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Check availability on Chester 2 Star Hotels

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chester 2-star hotels

A two-story building with a covered entrance and an American flag.
A hotel room with two beds, a chair, and a painting on the wall.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

1. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
CA $114
CA $125 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.
A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.
A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.
A hotel lobby with a reception desk, seating area, and dining space.

2. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
Silvia
CA $106
CA $121 total
includes taxes & fees
Oct 25 - Oct 26
Best Western Annapolis
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.
A modern office setup with two monitors, a keyboard, and two wooden chairs.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.
A buffet with labeled trays of turkey sausage and cookies.

3. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
Canada
Omer
CA $144
CA $164 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express & Suites Annapolis by IHG
A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.
Exterior
A restaurant with a counter, seating area, and a clock on the wall.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Wesley
CA $128
CA $142 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
An outdoor patio area with tables and chairs, covered by large orange umbrellas, and a brick building in the background.
A hotel lobby with a reception desk, a fireplace, and a colorful rug.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

5. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Courtney
CA $139
CA $158 total
includes taxes & fees
Oct 21 - Oct 22
Hampton Inn & Suites Annapolis
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

6. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Donna
CA $183
CA $202 total
includes taxes & fees
Oct 19 - Oct 20
Best Western Plus Easton Inn & Suites
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Crystal
CA $128
CA $143 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Grasonville near Kent Island
A modern living room with a large window, a dining area, and a kitchen in the background.
A hotel room with a bed, desk, chair, television, and a window with curtains.
A modern gym with weight racks, benches, and exercise equipment.
A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

8. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Darren
CA $132
CA $158 total
includes taxes & fees
Oct 25 - Oct 26
Candlewood Suites Annapolis by IHG
Two Adirondack chairs facing a calm body of water with a clear sky above.
A reception desk with a modern design, a digital display, and a check-in counter.
A modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
CA $149
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Annapolis East-Kent Island by IHG
A two-story house with a porch, a front door, and a small garden area.
A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.
A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

10. The Wildset

The Wildset
Downtown St. Michaels
United States
Sarah
CA $326
CA $394 total
includes taxes & fees
Nov 9 - Nov 10
The Wildset
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A gym with a treadmill, elliptical, and stationary bike.

11. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
United States
Edwin
CA $127
CA $139 total
includes taxes & fees
Oct 15 - Oct 16
Baymont by Wyndham Easton
A waterfront property with a covered patio, a dock, and a boat.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

12. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
United States
Gary
CA $283
CA $383 total
includes taxes & fees
Oct 25 - Oct 26
Wylder Tilghman Island
A hotel room with two beds, a desk, a TV, and a window with curtains.
A building with a sign reading "EcoLodge."
A breakfast bar with a waffle maker, coffee machine, and juice dispenser.
A covered corridor with a series of doors, each marked with a number.

13. Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
Easton
United States
Adriana
CA $115
CA $127 total
includes taxes & fees
Oct 21 - Oct 22
Econo Lodge Easton Route 50
A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A modern kitchen with a large island, bar stools, and a wine rack.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.

14. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Beverly
CA $264
CA $301 total
includes taxes & fees
Oct 18 - Oct 19
Anchored Inn at Hidden Harbour Marina
A hotel room with a bed, bedside tables, a desk, a TV, and a window with curtains.
A hotel safety and health protocol document.
A room with a door, a vending machine with snacks, and a trash bin.
A hotel hallway with carpeted floors, doors on both sides, and overhead lighting.

15. Red Roof Inn Annapolis

Red Roof Inn Annapolis
Annapolis
United States
Slobodan
CA $105
CA $120 total
includes taxes & fees
Oct 21 - Oct 22
Red Roof Inn Annapolis
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

16. Hampton Inn Easton

Hampton Inn Easton
Easton
United Kingdom
Rachel
CA $182
CA $200 total
includes taxes & fees
Nov 5 - Nov 6
Hampton Inn Easton
Private kitchen
Reception
Breakfast area
Room

17. Village Inn Annapolis MD

Village Inn Annapolis MD
Annapolis
United States
Keith
CA $118
CA $135 total
includes taxes & fees
Oct 19 - Oct 20
Village Inn Annapolis MD
A white two-story building with a central entrance, a staircase, and a small garden area.
A couple standing in front of a black wooden building with white-framed windows.
A table with a champagne bottle and glasses, a lamp, and a window with blinds.
A bookshelf with books, decorative items, and a fireplace.

18. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis
United States
Chris
CA $424
CA $484 total
includes taxes & fees
Oct 25 - Oct 26
134 Prince - Luxury Boutique Hotel
A two-story house with a covered porch, a staircase, and a garden area.
A row of stationary bicycles with green frames and white seats, parked outdoors.
A garden with a lawn and a table with chairs under a canopy.
A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

19. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
Joe
CA $190
CA $211 total
includes taxes & fees
Oct 21 - Oct 22
Haven Point Inn and Gallery
A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.
A church with a spire, surrounded by trees and illuminated by warm lights.
A cozy lounge area with a cushioned bench, two small tables with lamps, a brick wall, and a fireplace.
A living room with a fireplace, a chandelier, and a sofa.

20. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District
Norway
Jo
CA $390
CA $445 total
includes taxes & fees
Oct 19 - Oct 20
86 State Circle - Luxury Boutique Hotel
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Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Chester.
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle Annapolis MD
CA $122
CA $188 total
Oct 21 - Oct 22
includes taxes & fees
9/10 Wonderful! (2,049 reviews)
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD
CA $153
CA $174 total
Nov 11 - Nov 12
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Crowne Plaza Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

174 West Street Annapolis MD
CA $150
CA $171 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Hilton Garden Inn Annapolis Downtown
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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.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

See all hotels in Chester
A coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Find out more about Chester

Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Chester, Chester you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions.

Several of the best hotels with 2 Stars in Chester are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in Chester.

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