Find 2 Star Hotels in Chestertown, MD from $57

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Nov 26 - Nov 27
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Nov 27 - Nov 28
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Compare Chestertown 2 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1001)
"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "
United States
Carmen
$89 nightly
The price is $105
Dec 14 - Dec 15
Total with taxes and fees
Best Western Plus Hotel & Conference Center
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
Edgewood
7.4 out of 10, Good, (1024)
"Staff was very friendly. "
United States
Ashlee
$63 nightly
The price is $71
Nov 30 - Dec 1
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1005)
"Great place to stay"
United States
brian
$91 nightly
The price is $105
Nov 30 - Dec 1
Total with taxes and fees
Fairfield Inn & Suites by Marriott White Marsh
Lobby sitting area
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1005)
"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "
United States
Christeena
$51 nightly
The price is $57
Nov 30 - Dec 1
Total with taxes and fees
Americas Best Value Inn Edgewood
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1008)
"Would stay again"
United States
Dena
$82 nightly
The price is $91
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (799)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
$77 nightly
The price is $86
Dec 21 - Dec 22
Total with taxes and fees
Comfort Inn & Suites Aberdeen near APG
Free continental breakfast
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

2.5 star property
Nottingham
9.6 out of 10, Exceptional, (986)
"Everything was very nice stayed here for daughters lacrosse tournament."
United States
Melody
$99 nightly
The price is $115
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express White Marsh by IHG
Desk, laptop workspace, blackout drapes, iron/ironing board
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
Middle River
9.0 out of 10, Wonderful, (767)
"Great place to stay, better than any of the other hotels in the middle river area."
United States
Ed
$110 nightly
The price is $127
Dec 7 - Dec 8
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
Gift shop
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 star property
Glen Burnie
8.2 out of 10, Very Good, (1004)
"Quick easy and friendly check in. Clean room. Great stay for a business trip. Plenty of restaurants and easily accessible. "
United States
Michael
$92 nightly
The price is $105
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn Baltimore/Glen Burnie
Indoor pool
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

2.5 star property
Edgewood
7.2 out of 10, Good, (1007)
"The room was very comfortable and clean not very large though, perfect for my one night stay."
United States
Russell K
$70 nightly
The price is $78
Dec 3 - Dec 4
Total with taxes and fees
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Lobby
Extended Stay America Suites Baltimore Glen Burnie

Extended Stay America Suites Baltimore Glen Burnie

2.5 star property
Glen Burnie
6.4 out of 10, (785)
"Clean rooms"
United States
Thomas
$86 nightly
The price is $99
Dec 7 - Dec 8
Total with taxes and fees
Extended Stay America Suites Baltimore Glen Burnie
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (307)
"Great overall experience "
United States
Clement
$105 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very Good, (1005)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$84 nightly
The price is $93
Dec 3 - Dec 4
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 star property
Nottingham
7.6 out of 10, Good, (1008)
"Breakfast lady fabulous Staff very friendly "
United Kingdom
Alan
$87 nightly
The price is $101
Dec 9 - Dec 10
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (856)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$102 nightly
The price is $113
Nov 30 - Dec 1
Total with taxes and fees
Comfort Inn & Suites Chestertown
Lobby
WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham

2.5 star property
Nottingham
5.8 out of 10, (1001)
"Clean hotel friendly staff"
United States
Sheri
$82 nightly
The price is $95
Nov 30 - Dec 1
Total with taxes and fees
WoodSpring Suites Baltimore White Marsh - Nottingham
Vending machine
Red Roof Inn Edgewood

Red Roof Inn Edgewood

2.0 star property
Edgewood
7.2 out of 10, Good, (845)
"Room was runned down,staff was excellent,amenities ok,"
United States
Alane
$69 nightly
The price is $78
Nov 30 - Dec 1
Total with taxes and fees
Red Roof Inn Edgewood
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (417)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
$72 nightly
The price is $80
Dec 3 - Dec 4
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (853)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$85 nightly
The price is $94
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn
Lobby
Americas Best Value Inn Baltimore

Americas Best Value Inn Baltimore

2.0 star property
Pulaski Industrial Area
6.8 out of 10, (1000)
"Super staff and service. Good location and easy to reach. All basic facilities available. Friendly staff and easy check in. No breakfast(only coffee). "
United States
Anoop
$76 nightly
The price is $89
Nov 30 - Dec 1
Total with taxes and fees
Americas Best Value Inn Baltimore
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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 Chestertown.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

4 Philadelphia Ct Rosedale MD
$64 nightly
The price is $74 total per night from Dec 7 to Dec 8
$74 total
Dec 7 - Dec 8
Total with taxes and fees
7/10 Good! (1,069 reviews)
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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 Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

See all hotels in Chestertown
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"room was clean but the shower curtain was in tatters. multiple rings torn off"
Vincent 1-night trip
Posted 6 days ago
Red Roof Inn & Suites Chestertown
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"Staff is amazing & understanding "
Christeena 1-night trip
Posted 2 weeks ago
Americas Best Value Inn Edgewood

Find out more about Chestertown

When you've got to get away to a new or favorite destination without breaking the bank, Chestertown awaits with convenient 2 Star hotels and a change of scenery. Stay on your feet visiting top attractions that draw of visitors, or settle in for a hot cuppa nearby and watch the world around you. You're about to find out why both locals and travelers love this place.

The Ideal Accommodation at the Right Price

2 Star hotels are in high demand in Chestertown. You'll find the best deals right here, so book early and save on a great getaway. Thanks to several convenient locations and comfortable amenities, you'll find a place to stay that's just right for you. Stay here and be one of the first guests to review and share your thoughts. So, savor the comfort of a well-kept room and attentive hospitality. With our travel savings, the world is wide open to you one hotel at a time, and the journey starts in Chestertown.

Reserve Your Two-Star Hotel Today

Plan your trip to Chestertown now with Expedia's easy online travel booking and start relaxing before you even leave the house. Recently, traveling to this region has become cheaper due to more supply. Take advantage of the 2 Star Hotel availability and easy-going atmosphere.

Frequently asked questions

How much does it cost to stay in a 2-star hotel in Chestertown?
Travelers can find great deals on Chestertown 2-star hotels from $57 with Expedia – but remember that prices vary throughout the year. Factors like demand and location can affect hotel prices, and it's often more expensive to stay in Chestertown hotels during weekends, holidays and high season. Try searching for 2-star Chestertown hotels during midweek to track down the best deals.
What are the most highly rated Chestertown 2-star hotels?
In Chestertown, the Comfort Inn & Suites Chestertown is a highly rated choice among travelers, boasting an excellent review score of 8.6 out of 10. This inviting hotel offers attentive service and a friendly setting, superb for those seeking a relaxed stay. Guests appreciate the LGBTQIA-friendly environment, making it a comfortable option for all.

Another appealing option is the Driftwood Inn, which is designed with families in mind. Though it has a modest rating, what sets it apart are its child-friendly window designs and convenient amenities like microwaves and daily housekeeping. Families will appreciate the thoughtful touches that make traveling with children a bit easier.

While both properties provide a solid stay, they cater to different audiences—Comfort Inn & Suites for families and travelers looking for a welcoming experience, while Driftwood Inn focuses specifically on child-friendly features. Regardless of your choice, Chestertown offers a quaint escape with quality service that ensures a laid-back getaway.
Are there 2-star Chestertown hotels that offer free breakfast?
The Comfort Inn & Suites Chestertown is a charming two-star hotel that has a friendly setting, great for families and travelers seeking both comfort and convenience. With an excellent customer review rating of 8.6, this hotel provides a delightful complimentary breakfast every morning, ensuring you start your day off right without any added expense.
Are there family-friendly 2-star hotels in Chestertown?
When it comes to family-friendly hotels in Chestertown, the Comfort Inn & Suites Chestertown emerges as an excellent choice, boasting a great rating of 8.6 out of 10. This inviting hotel features a delightful pool, great for families looking to unwind after exploring the area. Additionally, the availability of free amenities for children, such as cribs and sofa beds, ensures that your little ones have a comfortable stay. With daily housekeeping and a complimentary breakfast on weekdays, parents can truly relax and enjoy their time away.

Another family-friendly option is the Red Roof Inn & Suites Chestertown, which offers a cozy environment with a rating of 7.4. This hotel provides free amenities for children, including cribs and sofa beds, making it a stress-free choice for families traveling with kids. The convenience of a microwave in the room allows for easy meal prep, ensuring everyone stays happy and fed.

Lastly, the Driftwood Inn also caters to families with its child-friendly window design and free amenities for children. Though it features a simpler setup, it maintains a inviting space ideal for families seeking a budget-friendly option.
Are there any 2-star Chestertown hotels with a pool?
The Comfort Inn & Suites Chestertown is a delightful two-star hotel that offers a welcoming retreat for families and travelers seeking a comfortable stay. With a traveler review rating of 8.6, this hotel stands out for its friendly space and attentive service.
Can I find pet-friendly 2-star hotels in Chestertown?
In Chestertown, the Comfort Inn & Suites Chestertown is a delightful option for travelers looking for a pet-friendly stay, boasting a great rating of 8.6 out of 10 from satisfied guests. This hotel not only welcomes pets but also provides a warm, inclusive setting, great for families who want to bring their furry companions along on their adventures.

Another great choice is the Red Roof Inn & Suites Chestertown, where pets are not only permitted but also welcomed with open arms. Rated 7.4 out of 10, this hotel offers essential amenities alongside a comfortable environment, making it a suitable pick for those traveling with pets.

For a charming and cozy alternative, the Driftwood Inn also allows pets, ensuring an easy experience for travelers who appreciate the company of their four-legged friends.
What is the difference between a 2-star Chestertown hotel and a 3-star hotel?
With all the home comforts travelers need, 2-star Chestertown hotels make a great base for exploring. These hotels are designed for convenience, and usually have comfy rooms, daily housekeeping services, and a 24-hour front desk. Some also have their own restaurant. For travelers who want to take things up a gear, 3-star Chestertown hotels might tick all the boxes. These mid-range hotels often have spacious rooms and extra amenities for a relaxing stay, such as a pool, gym, restaurant or bar.

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