Find 2 Star Hotels in Chestertown, MD from $56

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Check availability on Chestertown 2 Star Hotels

Tonight
Mar 23 - Mar 24
Tomorrow
Mar 24 - Mar 25
This weekend
Mar 27 - Mar 29
Next weekend
Apr 3 - Apr 5

Our top choices for Chestertown 2-star hotels

Exterior

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie
2.5 star property
Glen Burnie
8.2 out of 10, Very Good, (1,002 reviews)
"The hotel was great. The room was clean and spacious. The staff made us feel welcome."
United States
Shellyanne
$93 nightly
The price is $107
Apr 5 - Apr 6
Total with taxes and fees
Hampton Inn Baltimore/Glen Burnie
Lobby

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
2.5 star property
Medford
7.8 out of 10, Good, (1,006 reviews)
"Room was clean and quiet… will definitely return "
United States
Kelly
$107 nightly
The price is $125
Mar 29 - Mar 30
Total with taxes and fees
Best Western Plus Hotel & Conference Center
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,005 reviews)
"Clean room, nice staff and great breakfast "
United States
Curtis
$81 nightly
The price is $91
Mar 29 - Mar 30
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Lounge

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood
2.0 star property
Edgewood
5.8 out of 10, (1,001 reviews)
"The service was good and the room was was clean "
United States
Angela
$59 nightly
The price is $67
Mar 25 - Mar 26
Total with taxes and fees
Americas Best Value Inn Edgewood
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,007 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
$101 nightly
The price is $112
Mar 30 - Mar 31
Total with taxes and fees
Best Western Kent Narrows Inn
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very Good, (869 reviews)
"Would stay again! Very great place "
United States
Mindy
$81 nightly
The price is $91
Mar 30 - Mar 31
Total with taxes and fees
Comfort Inn & Suites Aberdeen near APG
Lobby lounge

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, (824 reviews)
"I enjoyed my stay and everything was perfect "
United States
Castro
$116 nightly
The price is $134
Apr 5 - Apr 6
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
Free daily continental breakfast

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, (1,062 reviews)
"It was a comfortable stay. "
United States
Fayaz
$59 nightly
The price is $66
Apr 12 - Apr 13
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
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, (1,000 reviews)
"Great hotel. Friendly staff and will stay again."
United States
Jennifer
$106 nightly
The price is $122
Apr 5 - Apr 6
Total with taxes and fees
Holiday Inn Express White Marsh by IHG
Exterior

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
2.5 star property
Nottingham
7.8 out of 10, Good, (1,001 reviews)
"Property was clean and it was a comfortable stay."
United States
Md Tanbir
$95 nightly
The price is $110
Mar 30 - Mar 31
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
Lobby

WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham
2.5 star property
Nottingham
5.8 out of 10, (1,004 reviews)
"Very respectful very kind I always have a good time here and we're coming back Sunday 🙂"
United States
Brandy
$82 nightly
The price is $95
Mar 25 - Mar 26
Total with taxes and fees
WoodSpring Suites Baltimore White Marsh - Nottingham
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, (1,005 reviews)
"Staff were very helpful! Certain areas smelled, but our room and the hotel overall was clean!"
United States
Taitym
$66 nightly
The price is $74
Mar 25 - Mar 26
Total with taxes and fees
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (890 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
$110 nightly
The price is $122
Apr 12 - Apr 13
Total with taxes and fees
Comfort Inn & Suites Chestertown
Lobby sitting area

Americas Best Value Inn Baltimore

Americas Best Value Inn Baltimore
2.0 star property
Pulaski Industrial Area
6.8 out of 10, (1,000 reviews)
"Everyone was great 👍"
United States
Dan c Hayley
$94 nightly
The price is $110
Apr 2 - Apr 3
Total with taxes and fees
Americas Best Value Inn Baltimore
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (887 reviews)
"Great place to stay"
United States
Ken
$104 nightly
The price is $115
Mar 30 - Mar 31
Total with taxes and fees
Hampton Inn Middletown
Lobby

Red Roof Inn Baltimore South - Glen Burnie

Red Roof Inn Baltimore South - Glen Burnie
2.0 star property
Ferndale
6.6 out of 10, (343 reviews)
"Not good "
United States
Gloria
$75 nightly
The price is $86
Mar 29 - Mar 30
Total with taxes and fees
Red Roof Inn Baltimore South - Glen Burnie
Free daily continental breakfast

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (580 reviews)
"No bar soap "
United States
Fataira
$92 nightly
The price is $103
Mar 26 - Mar 27
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Superior Room, 1 King Bed (Smoke Free) | In-room safe, desk, blackout drapes, free WiFi

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,001 reviews)
"Nasty "
United States
Tanesha
$50 nightly
The price is $56
Mar 25 - Mar 26
Total with taxes and fees
Red Roof Inn Aberdeen
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (974 reviews)
"Room was very clean, hotel staff was friendly and helpful!"
United States
Heather
$122 nightly
The price is $135
Apr 6 - Apr 7
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (884 reviews)
"Staff was nice and room was clean "
United States
Lauren
$93 nightly
The price is $104
Mar 29 - Mar 30
Total with taxes and fees
Quality Inn Grasonville near Kent Island
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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
$71 nightly
The price is $82 total per night from Apr 5 to Apr 6
$82 total
Apr 5 - Apr 6
Total with taxes and fees
7/10 Good! (1,181 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

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 $56 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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