Photo by Patricia Knorr

Chestertown Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chestertown hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (794)
"It was a clean comfortable spot to rest for the night. "
The price is P6,484
P7,197 total
includes taxes & fees
Aug 24 - Aug 25
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (386)
"Good location."
The price is P4,099
P4,549 total
includes taxes & fees
Aug 24 - Aug 25
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.2 out of 10, Very Good, (60)
"Great place to get some quiet rest by the water"
The price is P7,531
P8,360 total
includes taxes & fees
Aug 18 - Aug 19
The Lodge at Great Oak Landing

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (887)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is P7,913
P8,783 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Express Annapolis East-Kent Island by IHG

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

3.0 star property
7.0 out of 10, Good, (1005)
"I loved my stay"
The price is P4,600
P5,312 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (606)
"Great place to stay. "
The price is P9,279
P10,299 total
includes taxes & fees
Sep 15 - Sep 16
Hyatt Place Kent Narrows & Marina

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

2.5 star property
7.2 out of 10, Good, (1003)
"I liked everything about the hotel was very clean friendly staff "
The price is P3,065
P3,433 total
includes taxes & fees
Sep 7 - Sep 8
Quality Inn & Suites Bel Air I-95 Exit 77A

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1003)
"Great kid friendly place. Clean and nice breakfast buffet in the morning. Front desk staff are nice and polite. If I ever need a hotel in the area, I would be sure to stay here."
The price is P5,696
P6,579 total
includes taxes & fees
Sep 1 - Sep 2
Country Inn & Suites by Radisson, Baltimore North, MD

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (829)
"Everything is good for a business trip, simply sleep"
The price is P3,097
P3,468 total
includes taxes & fees
Sep 7 - Sep 8
Super 8 by Wyndham Aberdeen MD

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (983)
"Great spot with beautiful views. "
The price is P8,688
P9,644 total
includes taxes & fees
Sep 15 - Sep 16
Hilton Garden Inn Kent Island Marina

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1005)
"Great stay at a great price "
The price is P5,032
P5,636 total
includes taxes & fees
Aug 24 - Aug 25
Hampton Inn & Suites Edgewood/Aberdeen-South

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"
The price is P6,079
P7,143 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Hotel & Conference Center

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great location friendly staff "
The price is P5,758
P6,650 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield Inn & Suites by Marriott White Marsh

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1825)
"Great stay"
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (854)
" Very clean, spacious room, friendly staff"
The price is P13,500
P15,390 total
includes taxes & fees
Aug 24 - Aug 25
Annapolis Waterfront Hotel, Autograph Collection

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (109)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is P9,683
P12,843 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (954)
"The staff was great."
The price is P2,903
P3,252 total
includes taxes & fees
Aug 24 - Aug 25
Americas Best Value Inn Edgewood

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (410)
"Great location and amenities"
The price is P12,808
P15,665 total
includes taxes & fees
Aug 25 - Aug 26
The Inn at Chesapeake Bay Beach Club

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (747)
"Wonderful stay "
The price is P5,274
P5,907 total
includes taxes & fees
Aug 18 - Aug 19
Comfort Inn & Suites Aberdeen near APG

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (557)
"Great place to stay"
The price is P6,255
P7,006 total
includes taxes & fees
Aug 24 - Aug 25
Hampton Inn & Suites Baltimore/Aberdeen
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.
Save an average of 15% on thousands of hotels when you're signed in

Near an Attraction

Sumner Hall

Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.

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.

Photo by Assya A
Open Photo by Assya A

Best guest reviews of Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favorite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend Red Roof Inn & Suites Chestertown and Driftwood Inn as top options for your trip. See all available top hotels, or vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

What's the best hotel for families in Chestertown?

Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best accommodation for a romantic vacation to Chestertown?

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking. See all romantic hotels in Chestertown.

What's the best LGBTQ-friendly accommodation in Chestertown?

Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best pet-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

What's the best hotel to stay near the beach in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach. See more stays near the beach in Chestertown.

What's the best place to stay in Chestertown to absorb the local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also notable landmarks to visit include Historical Society of Kent County Maryland.

What are some accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness center. See all spa hotels in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 44 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit in Chestertown?

Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your agenda are Rolphs Wharf Marina and Chestertown Historic District. Check out what more to see and do in Expedia's Chestertown guide.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.