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Cheap Hotels in Chestertown, MD from $70

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Check availability on Chestertown Cheap Hotels

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Oct 2 - Oct 3
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Oct 3 - Oct 4
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Top Chestertown Cheap Hotels

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (399)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
$81 nightly
The price is $90
Oct 9 - Oct 10
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
$115 nightly
The price is $127
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
$64 nightly
The price is $70
Oct 27 - Oct 28
Total with taxes and fees
Driftwood Inn
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 out more about Chestertown

Find out more about Chestertown

Discover cheap things to do in Chestertown

Chestertown, Maryland, offers a blend of charming history and budget-friendly activities that will delight Quality Seekers. Start your adventure at the historic Chestertown Waterfront, where you can stroll along the picturesque streets, admire the historic architecture, and watch boats glide along the Chester River—all for free. Don't miss the Chestertown Farmers' Market, held every Saturday, where you can sample local produce and artisan goods without breaking the bank. For a bit of culture, visit the Kent County Arts Council, which often hosts free events and showcases local artists. Families will love the nearby Washington College, where you can take a self-guided campus tour and enjoy the beautiful grounds. When it comes to dining, check out the local favorites like The Fish Whistle, offering delicious seafood at reasonable prices, or try the laid-back atmosphere at Evergrain Bread Company for affordable sandwiches and coffee. For budget accommodations, look for hotels in the historic downtown area, where you can enjoy easy access to attractions while soaking in the charm of this quaint town. With plenty of affordable options and friendly service, Chestertown is sure to provide a memorable experience without straining your wallet.

Find the best cheap hotels in Chestertown

Travelers seeking budget-friendly accommodations in Chestertown, Maryland, will find these three excellent hotels that offer great value without compromising comfort.

Comfort Inn & Suites Chestertown

  • Why it's great for a budget-friendly vacation: For budget-conscious travelers, the Comfort Inn & Suites Chestertown stands out with a solid review rating of 8.6, making it a dependable choice for an affordable stay. The hotel offers complimentary breakfast options, including a full breakfast on weekends, ensuring guests start their day right without any extra costs. Free Wi-Fi and in-room internet access further enhance convenience during their visit.
  • Other amenities: In addition to budget amenities, guests can enjoy a range of features including a shared pool with sun loungers, a fitness center, and daily housekeeping to keep their accommodations tidy. The hotel also provides free self-parking, making it easy for travelers to explore the nearby historical district and enjoy local winery tours. With accessible facilities and a welcoming atmosphere, this hotel is a great option for those looking to experience Chestertown on a budget.
  • Nearby attractions: Rolling Road Park - 0.89 miles, Chestertown Dog Park - 0.95 miles

Red Roof Inn & Suites Chestertown

  • Why it's great for a budget-friendly vacation: The Red Roof Inn & Suites Chestertown offers an economical choice for travelers with a review rating of 7.2. This budget-friendly hotel provides essential amenities like free Wi-Fi, in-room internet access, and free self-parking, making it a practical option for those looking to save on their stay. The hotel also features complimentary cribs for families and has a location near the historical district for easy exploration.
  • Other amenities: Beyond the basics, guests can enjoy comfortable accommodations with air conditioning and microwaves in their rooms. Daily housekeeping ensures a straightforward experience, while the option for pet-friendly stays allows travelers to bring their furry friends along for the trip. With its focus on affordability and convenience, this hotel is perfect for budget travelers visiting Chestertown.
  • Nearby attractions: Rolling Road Park - 0.84 miles, Chestertown Dog Park - 0.9 miles

How can I get cheap hotels in Chestertown?

Best tips to find a cheap hotel in Chestertown

  1. If you're looking to travel to Chestertown on a budget, you'll be happy to know that you can find hotels for as low as $70. 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 $127. Staying a short amount of time in Chestertown 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 Chestertown, 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 Chestertown, 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 Chestertown, 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 Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Great stay"
Diedre 2-night trip
Posted 2 days ago
Best Western Plus Hotel & Conference Center

Frequently asked questions

What is Chestertown like for travelers on a budget?
Chestertown has a variety of cheap accommodations and places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Garfield Center for the Arts at the Prince Theater.
When is the best time for a budget trip to Chestertown?
Weather will likely play an important role when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to see and do in Chestertown?
You don't have to spend a fortune to find things to see and do in Chestertown. You can budget for the local attractions that interest you most, and then plan some activities that cost little or nothing at all. If you're eager to get outdoors, you can enjoy the natural setting at Chestertown Dog Park, Urieville Park, or Urieville Lake Fish Management Area.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The nearest airport is Baltimore, MD (MTN-Martin State), 20.3 mi (32.7 km) away. However, if that doesn't suit your budget, the next closest is 28.2 mi (45.3 km) away: Easton, MD (ESN-Easton - Newnam). Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see the area.

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