A boat docked at a pier during twilight with a city skyline in the background.

Find 2 Star Hotels in Chester, MD from $84

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Check availability on Chester 2 Star Hotels

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chester 2-star hotels

A two-story building with a covered entrance and an American flag.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
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
$99 nightly
$109 total
Oct 6 - Oct 7
Total with taxes and fees
St Michaels Inn
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.
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.
A gym with treadmills, elliptical machines, and exercise balls.

2. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
Sanaul
$80 nightly
$91 total
Oct 12 - Oct 13
Total with taxes and fees
Best Western Annapolis
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.
A microwave, a coffee maker, and a refrigerator in a kitchen area.
A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.
A modern office setup with two monitors, a keyboard, and two wooden chairs.

3. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
Canada
Omer
$110 nightly
$125 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
A hotel room with a large bed, bedside tables, a chair, a desk, a window with curtains, and a wall-mounted air conditioner.
A reception desk with a clock, framed pictures, and a sign for express checkout.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A poolside area with lounge chairs and a mural of a sunset over water.

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Beth
$115 nightly
$128 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Kent Narrows Inn
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.
A hotel lobby with a dining area, a fireplace, and a view of the outside.
A hotel room with two desks, two chairs, a carpeted floor, and artwork on the wall.

5. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Courtney
$98 nightly
$111 total
Nov 4 - Nov 5
Total with taxes and fees
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 pool area with multiple pools, lounge chairs, and a pool lift.
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

6. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Lori
$129 nightly
$142 total
Oct 6 - Oct 7
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A spacious lobby with a staircase, a reception desk, and a dining area.

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Crystal
$96 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
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.
An outdoor patio with a brick floor, surrounded by lush greenery and trees.
A modern gym with weight racks, benches, and exercise equipment.

8. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Darren
$97 nightly
$111 total
Nov 1 - Nov 2
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.
A reception desk with a modern design, a digital display, and a check-in counter.
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
$110 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
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 dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.
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.

10. The Wildset

The Wildset
Downtown St. Michaels
United States
Sarah
$252 nightly
$277 total
Nov 3 - Nov 4
Total with taxes and fees
The Wildset
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A gym with a treadmill, elliptical, and stationary bike.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

11. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
United States
Ellen
$89 nightly
$98 total
Oct 6 - Oct 7
Total with taxes and fees
Baymont by Wyndham Easton
A waterfront property with a covered patio, a dock, and a boat.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
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
$250 nightly
$275 total
Oct 25 - Oct 26
Total with taxes and fees
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 covered corridor with a series of doors, each marked with a number.
A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

13. Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
Easton
United States
Adriana
$81 nightly
$89 total
Oct 12 - Oct 13
Total with taxes and fees
Econo Lodge Easton Route 50
A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.
A modern kitchen with a large island, bar stools, and a wine rack.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A modern kitchen with a bar area, wooden flooring, and blue bar stools.

14. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Beverly
$229 nightly
$261 total
Oct 6 - Oct 7
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
A hotel room with two beds, a desk, a television, and a window with curtains.
A hotel with a parking lot, two red awnings, and a clear sky.
A hotel hallway with carpeted floors, doors on both sides, and overhead lighting.
A hallway with a stainless steel refrigerator, a vending machine, and a door.

15. Red Roof Inn Annapolis

Red Roof Inn Annapolis
Annapolis
United States
Slobodan
$74 nightly
$84 total
Oct 12 - Oct 13
Total with taxes and fees
Red Roof Inn Annapolis
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
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 hotel hallway with carpeted floors, white doors, and overhead lighting.

16. Hampton Inn Easton

Hampton Inn Easton
Easton
United Kingdom
Rachel
$128 nightly
$141 total
Oct 18 - Oct 19
Total with taxes and fees
Hampton Inn Easton
Private kitchen
Breakfast area
Coffee service
Room

17. Village Inn Annapolis MD

Village Inn Annapolis MD
Annapolis
United States
Keith
$83 nightly
$95 total
Oct 6 - Oct 7
Total with taxes and fees
Village Inn Annapolis MD
A white two-story building with a central entrance, a staircase, and a small garden area.
A dining room with a large rectangular table, six chairs, a chandelier, and a built-in bookshelf with various decorative items.
A couple standing in front of a black wooden building with white-framed windows.
A bookshelf with books, decorative items, and a fireplace.

18. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis
United States
Chris
$399 nightly
$455 total
Oct 18 - Oct 19
Total with taxes and fees
134 Prince - Luxury Boutique Hotel
A two-story house with a covered porch, a staircase, and a garden area.
A garden with a lawn and a table with chairs under a canopy.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
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
$135 nightly
$150 total
Oct 7 - Oct 8
Total with taxes and fees
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
$250 nightly
$286 total
Oct 6 - Oct 7
Total with taxes and fees
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
$125 nightly
$142 total
Nov 1 - Nov 2
Total with taxes and fees
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD
$111 nightly
$127 total
Nov 3 - Nov 4
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

174 West Street Annapolis MD
$114 nightly
$130 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
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Chester awaits: its island views, sunny weather, golf, and more!

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A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

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Chester Motel Guide

Planning a getaway with only a few bucks to spare? Expedia can help! With the inexpensive rates at the top motels in Chester, Maryland you can put together the vacation of your dreams without spending every penny of your yearly travel budget.

These smaller places are ideal if you need a home base that lets you easily explore the local sights; many of the best motels in Chester are located near major freeways and public transportation. Plus, when you book a cheap deal on a motel in Chester, you’ll find quiet rooms, complimentary toiletries, and comfortable sleeping areas, so you can unwind after a long day.

No matter which motel you choose, don't forget to use the travel tools at Expedia to search for local discounts, compare rates on the hottest motels, and plan your next vacation. You won't believe how budget-friendly an amazing getaway can be.

Also, feel free to check out the motels near me page to find the cheapest deals on motels near your current location.

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