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

Cheap Hotels in Chester, MD from $95

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Check availability on Chester Cheap Hotels

Tonight
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Chester cheap hotels

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 hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
jayne
$118 nightly
$131 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

2. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
$124 nightly
$138 total
Oct 13 - Oct 14
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A lobby with a reception desk, a clock, and a wall-mounted deer head.
A restaurant with a counter, seating area, and a clock on the wall.
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
$116 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Kent Narrows Inn
A large, two-story barn-style building with a covered front porch and a garage.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

5. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
$171 nightly
$186 total
Oct 14 - Oct 15
Total with taxes and fees
Kent Island Resort
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

6. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
$223 nightly
$247 total
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
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
Faezeh
$100 nightly
$111 total
Oct 7 - Oct 8
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A two-story building with a covered entrance and an American flag.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

8. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
$97 nightly
$106 total
Sep 21 - Sep 22
Total with taxes and fees
St Michaels Inn
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

9. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Chereis
$83 nightly
$95 total
Sep 27 - Sep 28
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A kitchen with a stone wall, a microwave, and various food items on the counter.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.
A residential area with a large building, a swimming pool, and well-maintained lawns.

10. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
United States
Erik
$98 nightly
$108 total
Sep 23 - Sep 24
Total with taxes and fees
Baymont by Wyndham Easton
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Find out more about Chester

Discover cheap things to do in Chester

Chester, Maryland, offers a delightful mix of budget-friendly activities and charming accommodations for the discerning traveler. First, explore the serene landscapes of the Chesapeake Bay by visiting the nearby Sandy Point State Park, where families can enjoy picnicking, hiking, and even free access to the beach. For a taste of local history, take a short drive to the historic town of Annapolis, where you can wander through the picturesque streets, admire historic architecture, and visit the Maryland State House, often free to enter. Adventure seekers will appreciate the thrilling experiences at the Chesapeake Bay Bridge, where walking or biking across offers stunning views at no cost. If your family enjoys the outdoors, the nearby Broadneck Park provides ample playgrounds and walking trails, perfect for an afternoon of fun. When it comes to dining, Chester boasts casual eateries like the popular Chick & Ruth's Delly, where kids can enjoy hearty meals without breaking the bank. For lodging, consider staying in the heart of Chester, where you’ll find a variety of affordable hotels with convenient access to these attractions, allowing you to easily explore the area while enjoying attentive service and comfortable amenities.

How can I get cheap hotels in Chester?

Best tips to find a cheap hotel in Chester

  1. If you're looking to travel to Chester on a budget, you'll be happy to know that you can find hotels for as low as $95. Of course, that price is affected by amenities, star rating, and even the time of year you visit. At most, hotel prices can be as high as $247. Staying a short amount of time in Chester is an effective way to reduce hotel costs.
  2. When you cut your vacation down to just a few days, you don't have to worry as much about hotel prices since you don't have that many nights to stay. For budget hotels in Chester, 3 to 4 days should be all the nights you need. That's generally enough to enjoy the city's top attractions, though there's certainly enough to do to warrant a week-long trip.
  3. When booking cheap hotel rooms in Chester, it's typically best to book about 3 weeks in advance. Book further in advance than that and you could be paying too much for your room, as hotels will often overestimate future demand. However, if you wait too long, you might find that the hotel has been completely booked.
  4. When you utilize search filters on Expedia, you'll be able to narrow down your results in a flash. These search filters cover a wide variety of factors you may be interested in when it comes to finding a cheap hotel in Chester, including amenities such as Free Breakfast, 2-star rating, or proximity to local attractions. You can even set filters for price limits to ensure that all the displayed results are within your budget.

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"From the check in to the check out this was a great experience. The staff were super friendly and helpful, the room was clean and comfortable and the location was fantastic. Free and ample parking added to the pluses. This hotel is an Annapolis gem and we will definitely be staying there again."
John 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Every thing was amazing. The staff was extremely helpful and the parking situation was perfect. Room was top notch."
Jennifer 4-night trip
Posted 2 hours ago
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"The pool was a lot smaller than the picture showed🙁"
Monica 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Could do better with parking it should be inclusive for handicapped people."
Fowler 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown
St Michaels Inn

St Michaels Inn

8/10 Good
"The one issue was there were flies in our room and a squished bug came on our wall. There also were cobwebs in the corner. Not enough pillows and old."
Rachel 1-night trip
Posted 2 days ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was amazing. Staff is super friendly and helpful. Plenty of parking. Would definitely stay again."
Michael 2-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Breakfast was really good but they never did get our door key to work properly. Room was very clean and bed was comfortable. Staff was very friendly and helpful but the outside of the rooms, such as doors needs serious upgrades."
Jane 1-night trip
Posted 3 days ago
Best Western Annapolis

Frequently asked questions

How much does a budget hotel in Chester cost?
Budget hotel prices in Chester vary, but you can find a great deal from $95 on Expedia. To find the cheapest budget hotels, be flexible with your dates—off-peak and mid-week stays are typically cheaper. Stretch your budget further by looking for hotels with free breakfast, free parking or free airport shuttles. Sort your search results by "Price: low to high" to see our lowest rates.
Which area of Chester is best to stay in for cheap hotels?
For travellers seeking cheap hotels in Chester, Maryland, the areas along the main thoroughfares, particularly near Route 50 and Route 18, offer the most affordable options. These locations provide easy access to local amenities and the Chesapeake Bay Bridge, without the higher prices sometimes associated with waterfront properties.Solo travellers will find a range of budget-friendly motels and inns scattered along these routes. While Chester itself is a smaller town, these accommodations serve as a practical base for exploring the wider Queen Anne's County area. Many of these establishments offer basic amenities, making them suitable for those primarily looking for a place to sleep after a day of exploring.For couples, staying slightly outside the immediate commercial hubs can sometimes yield better value. Consider areas a short drive from the main routes, where smaller, independently owned establishments might offer a more personal touch at a great price.
When is the most affordable time to visit Chester?
The most affordable time to visit Chester, Maryland, is typically during the off-peak seasons of late fall and early spring, avoiding the busy summer months. During these times, you'll find lower prices on accommodations and fewer crowds, making for a more relaxed and budget-friendly trip.For solo travellers, visiting between November and March (excluding holiday periods) offers the best value. Many local inns and guesthouses, particularly those offering charming waterfront views, may have reduced rates. Exploring the quiet streets of Chester and the nearby Kent Island becomes a peaceful experience, with opportunities for scenic walks along the Chesapeake Bay without the summer rush.Couples looking for a romantic getaway can also benefit from these shoulder seasons. Many restaurants, while still offering fresh Chesapeake seafood, might have special promotions or less demand for reservations, allowing for more spontaneous dining choices.
What free activities should we do in Chester?
For couples and solo travellers looking for free activities in Chester, Maryland, exploring the scenic outdoors and historical sites offers a rich experience without spending a dime. The town's location on Kent Island provides ample opportunities to enjoy the Chesapeake Bay's natural beauty and local history.Couples can enjoy a romantic stroll or a peaceful picnic at Terrapin Nature Park. This park features several miles of walking trails that wind through meadows and along the shoreline, offering stunning views of the Chesapeake Bay Bridge. It's an ideal spot for birdwatching and enjoying the sunset together. Solo travellers might find the tranquility of the park superb for a reflective walk or for capturing landscape photography.Another excellent free option is visiting the Kent Island Federation of Arts (KIFA) gallery. Located in a charming historic building, KIFA showcases local artists' work, providing a cultural experience that changes with each exhibition. It's a wonderful way to appreciate regional talent and engage with the local art scene.
Is it cheaper to book a Chester hotel and flight package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my budget hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right budget hotel in Chester for you.

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