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Find 2 Star Hotels in Chestertown, MD from $67

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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, (1005)
"The staff was very nice, the beds were comfortable, the breakfast selections were excellent. "
$102 nightly
The price is $116
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn Baltimore/Glen Burnie
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Great stay"
$107 nightly
The price is $125
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Hotel & Conference Center
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, (1005)
"Fine would stay again"
$62 nightly
The price is $69
Nov 2 - Nov 3
Total with 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, (1006)
"I loved EVERYTHING about this hotel!! We will definitely be back"
$97 nightly
The price is $112
Nov 2 - Nov 3
Total with 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
9.4 out of 10, Exceptional, (1003)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
$85 nightly
The price is $96
Oct 16 - Oct 17
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (747)
"Great place to stay, better than any of the other hotels in the middle river area."
$123 nightly
The price is $142
Oct 12 - Oct 13
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
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, (895)
"Was a great place to stay for 8 hours"
$78 nightly
The price is $88
Nov 3 - Nov 4
Total with taxes and fees
Days Inn by Wyndham Aberdeen
Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.8 out of 10, Good, (1001)
"Really enjoyed my stay, the staff were nice."
$95 nightly
The price is $110
Oct 16 - Oct 17
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
Americas Best Value Inn Edgewood
Lobby sitting area

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (988)
"I always have a good experience with the staff. The motel might not be the greatest, but the staff is always friendly and accommodating. That's why I keep coming back."
$60 nightly
The price is $67
Oct 12 - Oct 13
Total with taxes and fees
Americas Best Value Inn Edgewood
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1005)
"Great spot. "
$117 nightly
The price is $129
Nov 2 - Nov 3
Total with taxes and fees
Best Western Kent Narrows Inn
Holiday Inn Express Aberdeen by IHG
Terrace/patio

Holiday Inn Express Aberdeen by IHG

2.5 star property
8.6 out of 10, Excellent, (419)
"Very clean and wonderful staff "
$129 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
Holiday Inn Express Aberdeen 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, (775)
"Room was clean, price is very reasonable. "
$93 nightly
The price is $104
Nov 9 - Nov 10
Total with taxes and fees
Comfort Inn & Suites Aberdeen near APG
Extended Stay America Suites Baltimore Glen Burnie
Lobby

Extended Stay America Suites Baltimore Glen Burnie

2.5 star property
6.4 out of 10, (768)
"Overall it was a pretty good place to stay. "
$90 nightly
The price is $103
Nov 9 - Nov 10
Total with taxes and fees
Extended Stay America Suites Baltimore Glen Burnie
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, (400)
"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 16 - Oct 17
Total with taxes and fees
Red Roof Inn & Suites Chestertown
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, (944)
"Staff was very nice and rooms were clean. Breakfast was great too!!"
$95 nightly
The price is $110
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Express White Marsh by IHG
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (626)
"Check in staff was awesome!"
$103 nightly
The price is $115
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Express & Suites Middletown 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, (291)
"Friendly staff, comfortable bed and clean room "
$105 nightly
The price is $117
Oct 19 - Oct 20
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (826)
"Friendly staff, clean room, convenient location. "
$102 nightly
The price is $113
Oct 19 - Oct 20
Total with taxes and fees
Comfort Inn & Suites Chestertown
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Indoor pool

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

2.5 star property
7.2 out of 10, Good, (1004)
"I found the staff to be very friendly, I believe that it is a family owned / operated establishment and while the inside of the hotel "
$66 nightly
The price is $74
Oct 19 - Oct 20
Total with taxes and fees
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Red Roof Inn Aberdeen
Lobby lounge

Red Roof Inn Aberdeen

2.0 star property
6.4 out of 10, (1002)
"The area of the property was the best part lots of choices going out to eat close by hthe attendant I was nice however we had a issue with multiple flits and gnats I’ve killed so many only for them to be more in its place I couldn’t eat my food because it was so many gnats that crawled on my food were I couldn’t eat it."
$62 nightly
The price is $69
Oct 12 - Oct 13
Total with taxes and fees
Red Roof Inn Aberdeen
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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
$145 nightly
The price is $166 total per night from Nov 2 to Nov 3
$166 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,835 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
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
"Wish they had the pool open. The staff is great here and very helpful."
lisa 2-night trip
Posted 4 days ago
Red Roof Inn & Suites Chestertown

Find out more about Chestertown

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 $67 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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