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Check availability on Chestertown 2 Star Hotels

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

Hampton Inn Baltimore/Glen Burnie
Free daily continental breakfast

Hampton Inn Baltimore/Glen Burnie

2.5 star property
8.2 out of 10, Very Good, (1009)
"staff was super friendly and helpful. breakfast was delicious as well"
$118 nightly
The price is $135
Aug 31 - Sep 1
Total includes taxes and fees
Hampton Inn Baltimore/Glen Burnie
Quality Inn & Suites Bel Air I-95 Exit 77A
Desk, free WiFi, bed sheets, alarm clocks

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

2.5 star property
7.2 out of 10, Good, (1008)
"I liked everything about the hotel was very clean friendly staff "
$54 nightly
The price is $60
Sep 7 - Sep 8
Total includes taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Fairfield Inn & Suites by Marriott White Marsh
Free daily buffet breakfast

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1010)
"Great location friendly staff "
$101 nightly
The price is $117
Aug 31 - Sep 1
Total includes taxes and fees
Fairfield Inn & Suites by Marriott White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Great stay at a great price "
$88 nightly
The price is $99
Sep 2 - Sep 3
Total includes taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Holiday Inn Express White Marsh by IHG
Free continental breakfast

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (909)
"Loved it! I would totally stay there again."
$109 nightly
The price is $126
Aug 17 - Aug 18
Total includes taxes and fees
Holiday Inn Express White Marsh by IHG
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (746)
"Wonderful stay "
$93 nightly
The price is $104
Aug 17 - Aug 18
Total includes taxes and fees
Comfort Inn & Suites Aberdeen near APG
Days Inn by Wyndham Aberdeen
In-room safe, desk, soundproofing, iron/ironing board

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (880)
"Great price, nice staff. "
$63 nightly
The price is $71
Sep 1 - Sep 2
Total includes taxes and fees
Days Inn by Wyndham Aberdeen
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout drapes, iron/ironing board

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (719)
"Great stay"
$123 nightly
The price is $142
Aug 17 - Aug 18
Total includes taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.6 out of 10, Good, (1004)
"Clean area clean rooms friendly staff"
$87 nightly
The price is $101
Aug 31 - Sep 1
Total includes taxes and fees
Hampton Inn Baltimore/White Marsh
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
1 bedroom, in-room safe, desk, iron/ironing board

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

2.5 star property
7.2 out of 10, Good, (971)
"Great hotel"
$62 nightly
The price is $69
Sep 7 - Sep 8
Total includes taxes and fees
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (792)
"It was a clean comfortable spot to rest for the night. "
$114 nightly
The price is $126
Aug 17 - Aug 18
Total includes taxes and fees
Comfort Inn & Suites Chestertown
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, (385)
"Good location."
$72 nightly
The price is $80
Aug 19 - Aug 20
Total includes taxes and fees
Red Roof Inn & Suites Chestertown
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1000)
"Nice place nice the people work over there"
$107 nightly
The price is $125
Aug 31 - Sep 1
Total includes taxes and fees
Best Western Plus Hotel & Conference Center
Holiday Inn Express Aberdeen by IHG
Terrace/patio

Holiday Inn Express Aberdeen by IHG

2.5 star property
8.6 out of 10, Excellent, (405)
"Great staff"
$127 nightly
The price is $142
Sep 1 - Sep 2
Total includes taxes and fees
Holiday Inn Express Aberdeen by IHG
Extended Stay America Suites Baltimore Glen Burnie
Studio, 2 Double Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Extended Stay America Suites Baltimore Glen Burnie

2.5 star property
6.4 out of 10, (751)
"Overall it was a pretty good place to stay. "
$91 nightly
The price is $104
Aug 24 - Aug 25
Total includes taxes and fees
Extended Stay America Suites Baltimore Glen Burnie
Americas Best Value Inn Edgewood
Lobby sitting area

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (954)
"The staff was great."
$51 nightly
The price is $57
Aug 19 - Aug 20
Total includes taxes and fees
Americas Best Value Inn Edgewood
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
9.0 out of 10, Wonderful, (506)
"When I book hotels for work trips the breakfast at Holiday Inn is always great "
$100 nightly
The price is $112
Aug 17 - Aug 18
Total includes taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (259)
"Nice place to stay"
$107 nightly
The price is $119
Sep 3 - Sep 4
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (881)
"Great stay beautiful view"
$127 nightly
The price is $141
Aug 24 - Aug 25
Total includes taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (806)
"Conveniently located with overall great value."
$98 nightly
The price is $108
Aug 24 - Aug 25
Total includes taxes and fees
Quality Inn
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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.
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle, Annapolis, MD
$143 nightly
The price is $163 total per night from Aug 19 to Aug 20
$163 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (1,829 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

Quaint Chestertown awaits: its sports, university life, festivals, and more!

See all hotels in Chestertown
Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Great service "
Maria 3-night trip
Posted 11 days ago
Red Roof Inn & Suites Chestertown

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.