An aerial view of a town with a river, buildings, and surrounding greenery.

Find 2 Star Hotels in Chestertown, MD from $69

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Check availability on Chestertown 2 Star Hotels

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Chestertown 2-star hotels

Free daily continental breakfast
Free daily continental breakfast
Reception
Free daily continental breakfast

1. Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie
Glen Burnie
United States
Helena
$107 nightly
$122 total
Sep 27 - Sep 28
Total with taxes and fees
Hampton Inn Baltimore/Glen Burnie
Lobby
Free daily buffet breakfast
Lobby
Breakfast, lunch and dinner served

2. Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
Medford
United States
Wendy
$111 nightly
$125 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Plus Hotel & Conference Center
Reception
Reception
Two queen studio suite | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels
Pool

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
$84 nightly
$95 total
Sep 29 - Sep 30
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Free daily continental breakfast
Point of interest
Property amenity
Lobby

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
United States
Nina
$62 nightly
$69 total
Sep 27 - Sep 28
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby
Seasonal outdoor pool
In-room safe, desk, soundproofing, iron/ironing board
Exterior

5. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
Aberdeen
United States
Luis
$66 nightly
$73 total
Sep 20 - Sep 21
Total with taxes and fees
Days Inn by Wyndham Aberdeen
Lobby lounge
Desk, laptop workspace, blackout drapes, iron/ironing board
Lobby
View from property

6. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Shanette
SpringHill Suites Baltimore White Marsh/Middle River
Exterior
Lobby
Suite, 1 Queen Bed | Hypo-allergenic bedding available, desk, laptop workspace
Terrace/patio

7. Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
Nottingham
United States
Cassie
$102 nightly
$117 total
Sep 23 - Sep 24
Total with taxes and fees
Hampton Inn Baltimore/White Marsh
Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave | In-room safe, desk, laptop workspace, iron/ironing board
Property amenity
Free daily full breakfast
Indoor pool

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
$116 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Kent Narrows Inn
Free continental breakfast
In-room safe, soundproofing, WiFi (free), bed sheets
Exterior
Indoor pool

9. Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG
Nottingham
United States
Kevin
$113 nightly
$131 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express White Marsh by IHG
Exterior
Desk, laptop workspace, blackout drapes, iron/ironing board
Lobby lounge
Desk, laptop workspace, blackout drapes, iron/ironing board

10. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
$72 nightly
$80 total
Sep 24 - Sep 25
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Lounge
Lobby sitting area
Lounge
Lounge

11. Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood
Edgewood
United States
Chiffon
$65 nightly
$73 total
Sep 18 - Sep 19
Total with taxes and fees
Americas Best Value Inn Edgewood
Lobby sitting area
Free daily full breakfast
Lobby lounge
Suite, Multiple Beds, Accessible, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

12. Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
Aberdeen
United States
Mitchell
$72 nightly
$80 total
Sep 28 - Sep 29
Total with taxes and fees
Comfort Inn & Suites Aberdeen near APG
Free daily full breakfast
Lobby
Point of interest
Lobby

13. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
$107 nightly
$119 total
Oct 14 - Oct 15
Total with taxes and fees
Comfort Inn & Suites Chestertown
Room, 2 Queen Beds, Accessible, Non Smoking | Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)
Exterior
Lobby

14. WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham
Nottingham
United States
Billy
$80 nightly
$92 total
Sep 20 - Sep 21
Total with taxes and fees
WoodSpring Suites Baltimore White Marsh - Nottingham
Exterior
Lobby
In-room safe, iron/ironing board, WiFi (free), bed sheets
Exterior

15. Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
Middletown
United States
John
$101 nightly
$112 total
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Desk, blackout drapes, iron/ironing board, cribs/infant beds
Fitness facility
Room amenity
Interior

16. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
United States
Dalton
$88 nightly
$99 total
Sep 29 - Sep 30
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets
Free buffet breakfast
Lobby
Exterior

17. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
John
$100 nightly
$111 total
Oct 12 - Oct 13
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Exterior
Free daily buffet breakfast
Exterior
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board

18. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
jayne
$111 nightly
$123 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Desk, laptop workspace, blackout drapes, iron/ironing board
Free daily on-the-go breakfast
Exterior
Lobby

19. Extended Stay America Suites Baltimore Glen Burnie

Extended Stay America Suites Baltimore Glen Burnie
Glen Burnie
United States
Kiema
$79 nightly
$90 total
Sep 24 - Sep 25
Total with taxes and fees
Extended Stay America Suites Baltimore Glen Burnie
Bar (on property)
Bar (on property)
Premium bedding, in-room safe, desk, iron/ironing board
Exterior

20. Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen
Aberdeen
United States
Julie
$65 nightly
$73 total
Sep 20 - Sep 21
Total with taxes and fees
Travelodge by Wyndham 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.
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
$82 total
Sep 27 - Sep 28
Total with taxes and fees
7/10 Good! (1,238 reviews)
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle Annapolis MD
$148 nightly
$169 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,998 reviews)
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

2112b Emmorton Park Rd Edgewood MD
$79 nightly
$88 total
Sep 20 - Sep 21
Total with taxes and fees
8.2/10 Very Good! (1,142 reviews)
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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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
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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 $69 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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