---
title: "Cheap Hotels in Chestertown | Free Cancellation Options - Expedia"
description: "Learn more about Cheap Hotels in Chestertown with Expedia. Read verified reviews, check availability, and book the stay that fits your trip. Great prices from $70"
canonical: "https://www.expedia.com/Chestertown-Hotels-Cheap-Hotels.0-0-d7215-tCheapHotels.Travel-Guide-Filter-Hotels"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-13T03:03:19Z
---

Plan your trip

- [Chestertown Travel Guide](https://www.expedia.com/Chestertown.dx7215)
- [Hotels in Chestertown](https://www.expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)
- [Flights to Chestertown](https://www.expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)
- [Car Rentals in Chestertown](https://www.expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)
- [Chestertown Vacation Packages](https://www.expedia.com/Chestertown.d7215.Destination-Travel-Guides)
- [Vacation Rentals in Chestertown](https://www.expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)

# Cheap Hotels in Chestertown, MD from $70
![A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

[Check prices for these dates, December 13 – 14, 2026](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-12-13&endDate=2026-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget%5Fproperty)

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## Our top choices for Chestertown cheap hotels

### [1\. Historic Inns of Annapolis](https://www.expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Historic District
- Guest rating: 9/10 (Wonderful, 2065 reviews)
- Price: $106 nightly, $120 total, Dec 3 - Dec 4, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Great location, excellent stay, by Christiaan

### [2\. Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

![A hotel lobby with a fireplace, seating area, and a television.](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/8d9295fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chestertown
- Guest rating: 8.6/10 (Excellent, 1000 reviews)
- Price: $96 nightly, $107 total, Dec 6 - Dec 7, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: The front desk staff were so nice, room very clean., by John

### [3\. Great Wolf Lodge Perryville](https://www.expedia.com/Perryville-Hotels-Great-Wolf-Lodge-Perryville.h103097849.Hotel-Information)

![An indoor water park with multiple slides, a water fountain, and seating areas.](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/31e21486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Perryville
- Guest rating: 8.6/10 (Excellent, 365 reviews)
- Price: $207 nightly, $232 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Our stay was perfect!, by Catherine

### [4\. Red Roof Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

![A living room with a fireplace, a television, and a stone accent wall.](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/52e5598b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chestertown
- Guest rating: 7.2/10 (Good, 514 reviews)
- Price: $72 nightly, $80 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again., by Regina

### [5\. Driftwood Inn](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information)

![A row of motel rooms with stone walls and red doors.](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chestertown
- Guest rating: 5.4/10 (183 reviews)
- Price: $64 nightly, $70 total, Nov 14 - Nov 15, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: It was a nice, clean place to stay the night., by Kathy

### [6\. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://www.expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information)

![A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Rossville
- Guest rating: 7/10 (Good, 1264 reviews)
- Price: $67 nightly, $78 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: The front desk staff was very helpful and pleasant check in was easy and check out also room was spacious, by Lavona

### [7\. The Lodge at Great Oak Landing](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information)

![A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Chestertown
- Guest rating: 8/10 (Very good, 129 reviews)
- Price: $124 nightly, $137 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area., by William

### [8\. Hilton Garden Inn Annapolis Downtown](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

![A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/w5752h3837x5y3-99f5dc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Annapolis
- Guest rating: 8.6/10 (Excellent, 1011 reviews)
- Price: $98 nightly, $111 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Great location, friendly staff., by Joel

### [9\. Graduate by Hilton Annapolis](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![A spacious atrium with a high ceiling, skylights, and a patterned floor.](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Annapolis
- Guest rating: 9.2/10 (Wonderful, 1014 reviews)
- Price: $130 nightly, $149 total, Nov 29 - Nov 30, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Brunch was the best we had the whole trip! Excellent food and wonderful staff., by REBECCA

### [10\. Hampton Inn Baltimore/White Marsh](https://www.expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.Hotel-Information)

![A Hampton Inn with a 'Welcome' sign under a covered entrance, surrounded by greenery.](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Nottingham
- Guest rating: 7.8/10 (Good, 1001 reviews)
- Price: $102 nightly, $117 total, Nov 19 - Nov 20, Total with taxes and fees, for Our top choices for Chestertown cheap hotels
- Review: Awesome hotel breakfast was good hotel was clean, by Kisha

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.

[View all properties](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=7215&adults=2&sort=BUDGET&openPlayBack=true)

## Top Chestertown Hotel Reviews

### [Inn at Huntingfield Creek](https://www.expedia.com/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information)

![A boat deck with a white bench and a view of a calm lake and distant trees.](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Rock Hall
- Review: Quaint property - very laid-back. Exactly what we were looking for., by George, February 28, 2023, rated 10/10 Excellent

### [134 Prince - Luxury Boutique Hotel](https://www.expedia.com/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information)

![A white two-story building with a central entrance, a staircase, and a small garden area.](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Annapolis
- Review: Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!, by Reyna, February 15, 2025, rated 10/10 Excellent

### [86 State Circle - Luxury Boutique Hotel](https://www.expedia.com/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information)

![A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Historic District
- Review: The property was immaculate! The room we stayed (Chase suite) was gorgeous!! The staff were so wonderful and helpful and the location was perfect. Loved everything about this property, by MARA, October 31, 2026, rated 10/10 Excellent

### [Hyatt Place Kent Narrows & Marina](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Grasonville
- Review: Loved it, by Joe, May 6, 2025, rated 10/10 Excellent

### [Hampton Inn & Suites Edgewood/Aberdeen-South](https://www.expedia.com/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information)

![A modern hotel lobby with a long dining table, several chairs, and a bar area.](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/38012dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Edgewood
- Review: Lovely clean hotel with nice breakfast options. Clean & comfortable accommodations and polite and welcoming staff., by John, October 21, 2024, rated 10/10 Excellent

### [Hilton Garden Inn Bel Air](https://www.expedia.com/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information)

![A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ff957644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Bel Air
- Review: Everything was excellent! Clean room, comfortable bed, friendly and helpful staff. We also enjoyed the pool and the on-site restaurant. Chef Dave’s cooking was delicious, we would go back for dinner even if we weren’t staying there!, by Ami, January 2, 2023, rated 10/10 Excellent

### [The Inn at Chesapeake Bay Beach Club](https://www.expedia.com/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information)

![A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Stevensville
- Review: Beautiful place, quiet and clean., by Chuck, May 15, 2025, rated 10/10 Excellent

### [Holiday Inn Express White Marsh by IHG](https://www.expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information)

![A modern breakfast area with labeled dispensers for yogurt, eggs, and milk, a coffee machine, and a chalkboard menu.](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Nottingham
- Review: Nice place, by Shaine, November 11, 2026, rated 10/10 Excellent

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

![Two Adirondack chairs facing a calm body of water with a clear sky above.](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Grasonville
- Review: The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look..., by Christina, July 17, 2023, rated 10/10 Excellent

### [Pendry Baltimore](https://www.expedia.com/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information)

![A modern living room with a fireplace, two sofas, a coffee table with a book, and a view of the sea.](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/69afdf6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Fells Point
- Review: Staff was excellent. Housekeeping went above & beyond to clean. Heated bathrooms floors were great!, by Amy, January 3, 2025, rated 10/10 Excellent

### [Kent Island Resort](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

![A large, two-story barn-style building with a covered front porch and a garage.](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Stevensville
- Review: I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay., by John, March 27, 2025, rated 10/10 Excellent

### [Fairfield Inn & Suites by Marriott Middletown](https://www.expedia.com/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

![A modern building with a patio area featuring outdoor seating and a fire pit.](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Middletown
- Review: Very nice hotel. One breakfast complaint: As with so many hotels, no sense of what tea-drinkers want. A wide selection of flavored "teas" (which are not actually teas), but no simple, normal tea, such as an English Breakfast Tea. This may seen like nit-picking, but it isn't to tea drinkers. You would never treat coffee drinkers this way., by Anonymous traveler, August 6, 2024, rated 10/10 Excellent

### [Holiday Inn Express & Suites Middletown by IHG](https://www.expedia.com/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

![A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3c1144bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Middletown
- Review: Clean room, and a breakfast. No issues at all., by Paula, November 6, 2026, rated 10/10 Excellent

### [The Inn at Henderson's Wharf, an Ascend Collection Hotel](https://www.expedia.com/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information)

![A large brick building with a waterfront view, a flag, and a dock with boats.](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/69872362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Fells Point
- Review: Just got back from a three night stay. The property was safe, clean and quiet. The hotel is near plenty of restaurants and bars within walking distance. We went to the Ravens game and got to the stadium via ride share very easily then walked half way back until we found some Lime scooters and rode the rest of the way. The room was spacious. Breakfast was served daily. It was nothing special but it was convenient for sure. It was nice that they usually had free cookies sitting out throughout the..., by Megan, September 17, 2024, rated 10/10 Excellent

### [Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG](https://www.expedia.com/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information)

![A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/70c9119c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Edgewood
- Review: Stay here with two friends. The room was very clean and the beds comfortable. There is an indoor that looked nice though we did not use it. The Front desk guy on checkin was very friendly and helpful, by Heather, January 18, 2025, rated 10/10 Excellent

### [SpringHill Suites Baltimore White Marsh/Middle River](https://www.expedia.com/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information)

![A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/d7725583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Middle River
- Review: We like how close it is to the shopping center, but that it's in a quieter area. This was our second time there and the cleanliness of the bathroom was a little disappointing but otherwise it was good., by Rachael, October 8, 2019, rated 10/10 Excellent

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

![A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 58 State Circle, Annapolis, MD, 21401, US
- Location: Historic District
- Star rating: 3.5/5
- Guest rating: 9/10 (2065 reviews)
- Review: Lovely property in the heart of Annapolis. Quiet yet convenient to downtown. Connor was awesome! He took care of our every need., by Robert, February 19, 2024, rated 10/10 Excellent

## Find out more about Chestertown

### Discover cheap things to do in Chestertown

Chestertown offers a delightful blend of history, culture, and natural beauty that budget-conscious travelers can explore without breaking the bank. Start your adventure by strolling along the picturesque waterfront, where you can enjoy free views of the scenic river and watch the boats glide by. For those interested in history, the charming downtown area features beautifully preserved historic buildings that tell the story of the town's rich past—perfect for a leisurely walking tour. If you’re looking for art and culture, local galleries often host free exhibitions, allowing you to appreciate the creativity of the community. Outdoor enthusiasts can take advantage of the lovely parks scattered throughout the town, which are ideal for picnics or a relaxing afternoon with family. Don’t miss out on sampling the local cuisine; many small eateries offer delicious, affordable meals that showcase regional flavors. For an enjoyable stay, consider booking a hotel in the heart of downtown, where you'll have easy access to these attractions and a vibrant atmosphere that enhances your Chestertown experience.

### Find the best cheap hotels in Chestertown

For budget-conscious travelers visiting Chestertown, there are several hotels that offer great value without compromising comfort. Here are two top picks that provide essential amenities to ensure a pleasant stay.

[**Comfort Inn & Suites Chestertown**](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

- **Why it's great for a budget-friendly vacation:**  Great for budget travelers, the Comfort Inn & Suites Chestertown has a welcoming atmosphere with essential amenities. With an impressive review rating of 9 out of 10, this budget-friendly option features complimentary breakfast, free WiFi, and convenient self-parking, making it an excellent choice for those looking to save while enjoying their stay.
- **Other amenities:**  Guests will appreciate the daily housekeeping service and designer toiletries provided in each room. The hotel also features a shared pool with accessible options and sun loungers, perfect for relaxation. Additional amenities include a hydromassage showerhead, a microwave in rooms, and contactless check-in for added convenience. Family-friendly features such as cribs and free services for children are available, ensuring a comfortable experience for all.
- **Nearby attractions:**  Kings Town Park - 2 miles, Roundtop Park - 5 miles, Urieville Park - 5 miles

[**Red Roof Inn & Suites Chestertown**](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information)

- **Why it's great for a budget-friendly vacation:**  The Red Roof Inn & Suites Chestertown is an ideal choice for budget travelers seeking a comfortable stay. With a review rating of 7 out of 10, this budget-friendly hotel offers free WiFi, self-parking, and cribs at no extra cost, ensuring a straightforward experience for travelers.
- **Other amenities:**  This hotel welcomes pets and features designated areas for smoking. Guests can enjoy a microwave in their rooms and daily housekeeping service. The hotel is situated in the historical district, allowing easy access to local attractions. Additional offerings include air conditioning and sofa beds for added comfort. The friendly, welcoming atmosphere makes it a great choice for all types of travelers.
- **Nearby attractions:**  Washington College - less than 1 mile, Rolling Road Park - less than 1 mile, Chestertown Dog Park - less than 1 mile

## Frequently Asked Questions

### How much does a budget hotel in Chestertown cost?

Budget hotel prices in Chestertown vary, but you can find a great deal from $70 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.

### What are the top-rated cheap hotels for families in Chestertown?

For top-rated, budget-friendly hotels in Chestertown that cater to families, consider the [Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) and the [Red Roof Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information).

Comfort Inn & Suites Chestertown, with an 8.6 rating, offers excellent value with complimentary breakfast, including a full breakfast option, and free WiFi. Guests frequently highlight the comfortable and clean rooms, as well as the friendly and helpful staff, particularly at the front desk. It is conveniently located near Chestertown Dog Park and Rolling Road Park.

Red Roof Inn & Suites Chestertown, rated 7.2, provides families with free WiFi, free self-parking, and complimentary cribs. Reviewers often mention the comfortable and clean rooms, the nice and lovely staff, and the easy parking. This hotel is also close to Chestertown Dog Park and Rolling Road Park.

### What cheap hotels in Chestertown offer complimentary breakfast?

For a budget-friendly stay in Chestertown that includes a complimentary breakfast, [Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) is an excellent choice.

This Comfort Inn & Suites Chestertown, rated 8.6 by guests, offers a generous free full breakfast, ensuring a great start to your day. Travellers frequently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff, particularly at the front desk. In addition to the breakfast, you'll also benefit from complimentary WiFi and free self-parking, adding to the overall value.

### When is the most affordable time to visit Chestertown?

The most affordable time to visit Chestertown, Maryland, is generally during the shoulder seasons of spring (April-May) and fall (September-October), and especially in the off-season winter months (November-March), excluding holiday periods. During these times, you'll find lower prices on accommodations and potentially fewer crowds, allowing for a more relaxed and budget-friendly experience.

Solo travellers and couples will appreciate the quiet charm of Chestertown during these periods. Many local shops and restaurants remain open, offering a genuine taste of the Eastern Shore without the peak season premiums. You can enjoy strolls along the Chester River waterfront, explore historic streets, or visit local art galleries for free or at a low cost. The cooler weather in fall and winter can also make outdoor activities like hiking or biking on nearby trails more pleasant.

While summer offers more festivals and river activities, the demand drives up prices for lodging and dining.

### What are the best cheap hotels in Chestertown with a pool?

For budget-friendly hotels in Chestertown that feature a pool, [Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) is an excellent choice.

Comfort Inn & Suites Chestertown, with an 8.6 review rating, offers a seasonal outdoor pool, superb for relaxation. Guests regularly highlight the comfortable and clean rooms and beds, as well as the friendly and helpful staff. A complimentary full breakfast is provided, ensuring a great start to your day, and free WiFi and free self-parking add to the value. It is conveniently located near Chestertown Dog Park and Rolling Road Park.

### Are there any cheap Chestertown hotels near Wilmer Park?

For an affordable hotel near Wilmer Park in Chestertown, the [Driftwood Inn](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information) is an excellent option.

The Driftwood Inn offers great value with free self-parking, complimentary toiletries, and free WiFi, which helps keep travel costs down. Guests frequently mention the clean rooms and friendly staff in their reviews.

### Is Chestertown a budget-friendly destination?

Yes, Chestertown, Maryland, is a budget-friendly destination, especially for those seeking a charming historical experience without breaking the bank. Its compact size and focus on natural beauty and local culture contribute to its affordability.

Solo travellers and couples will find that many of the town's main attractions are free or low-cost. Strolling along the waterfront and admiring the historic architecture of the town centre are enjoyable activities that don't cost a thing. The town's small scale also means transportation costs are minimal; most points of interest are easily accessible on foot.

Dining can also be economical, with several casual eateries offering delicious local fare at reasonable prices. Exploring the local shops and galleries provides a pleasant diversion, and many offer unique, handcrafted items that make for meaningful souvenirs.

### Which cheap hotels in Chestertown have good reviews for customer service?

For affordable hotels in Chestertown with great customer service, travellers frequently praise [Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information), [Red Roof Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information), and [Driftwood Inn](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information).

The Comfort Inn & Suites Chestertown, with an 8.6 review rating, offers excellent value with complimentary amenities like free WiFi, a full breakfast, and toiletries. Guests consistently highlight the great service and the friendly, helpful front desk staff. It is conveniently located near Chestertown Dog Park and Rolling Road Park.

Red Roof Inn & Suites Chestertown, rated 7.2, provides guests with free WiFi, free self-parking, and complimentary toiletries, along with free cribs for families. Reviewers often mention the lovely and nice staff. This hotel is also close to Chestertown Dog Park and Rolling Road Park.

Driftwood Inn offers free self-parking, free WiFi, and complimentary toiletries, making it a budget-friendly option. Customers frequently praise the friendly staff.

### Are there any cheap hotels in Chestertown that allow for late check-out or early check-in?

For travellers seeking a budget-friendly hotel in Chestertown with flexible check-in or check-out options, [Comfort Inn & Suites Chestertown](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) is a great choice.

Comfort Inn & Suites Chestertown, with an 8.6 rating, offers a variety of amenities that add significant value to your stay, including a complimentary full breakfast, free WiFi, and free self-parking. Guests frequently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff, particularly at the front desk. This hotel is conveniently located near Chestertown Dog Park and Rolling Road Park, providing opportunities for outdoor activities.

### What free activities should we do in Chestertown?

Families traveling to Chestertown, Maryland, can enjoy a variety of engaging and enriching free activities that highlight the town's historical charm and natural beauty. Exploring the Chestertown Historic District on foot is a must, where you can admire the beautifully preserved 18th-century architecture and imagine life in historic times.

A visit to Wilmer Park offers scenic views of the Chester River, a great spot for a picnic or simply watching the boats go by. The park also features a playground, providing a delightful diversion for younger family members. For a deeper dive into the town's past, consider a self-guided tour of the Chestertown Tea Party Festival sites, which commemorate a significant event in American history.

### Is it cheaper to book a Chestertown 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](https://www.expedia.com/Chestertown.d7215.Destination-Travel-Guides).

### 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 Chestertown for you.

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