Chestertown accommodation from AU$106

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Check hotel availability in Chestertown

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Check prices in Chestertown for tonight, 15 May - 16 May
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Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is AU$206 per night
AU$206
per night
20 May - 21 May
1.02 km from city centre
Comfort Inn & Suites Chestertown: Pet-friendly hotel with free breakfast and free WiFi. Located in the historical district.
Pet-friendly
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is AU$128 per night
AU$128
per night
21 May - 22 May
0.93 km from city centre
Red Roof Inn & Suites Chestertown: Pet-friendly hotel with free WiFi and free parking. Located in the city centre.
Pet-friendly
Laundry
Free cancellation
Reserve now, pay when you stay
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
The price is AU$276 per night
AU$276
per night
28 May - 29 May
45.06 km from city centre
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
Pet-friendly
Laundry
Free cancellation
Reserve now, pay when you stay
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
The price is AU$597 per night
AU$597
per night
28 May - 29 May
45.57 km from city centre
Sagamore Pendry Baltimore: Luxury hotel with free WiFi and outdoor pool. Located in the historical district.
Pet-friendly
Spa
Free cancellation
Reserve now, pay when you stay
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
The price is AU$190 per night
AU$190
per night
2 Jun - 3 Jun
41.74 km from city centre
Best Western Plus Hotel & Conference Center: Pet-friendly hotel with free breakfast and free WiFi. Located in the business district.
Hot tub
Pet-friendly
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie

La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie

2.5 out of 5
6323 Ritchie Highway, Glen Burnie, MD
The price is AU$130 per night
AU$130
per night
21 May - 22 May
46.96 km from city centre
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie: Pet-friendly hotel with free breakfast and free WiFi. Located near a train station.
Pet-friendly
Pool
Free cancellation
Reserve now, pay when you stay
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
The price is AU$426 per night
AU$426
per night
27 May - 28 May
45.01 km from city centre
Annapolis Waterfront Hotel, Autograph Collection: Pet-friendly hotel with free WiFi and a bar/lounge. Located on the waterfront.
Pet-friendly
Breakfast available
Quality Inn & Suites Bel Air I-95 Exit 77A

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

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
The price is AU$106 per night
AU$106
per night
16 May - 17 May
33.28 km from city centre
Quality Inn & Suites Bel Air I-95 Exit 77A: Business-friendly hotel with free breakfast and free WiFi. Guests love the comfy beds!
Breakfast included
Parking included
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

2.5 out of 5
6571 Eastern Avenue, Baltimore, MD
The price is AU$255 per night
AU$255
per night
9 Jun - 10 Jun
40.88 km from city centre
Hampton Inn Baltimore Bayview Campus: Pet-friendly hotel with free breakfast and free WiFi. Located near the airport.
Pet-friendly
Pool
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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.

Accommodation in Chestertown

Chestertown is a marvellous place to check out, with a neat little list of available hotels. There are 4 located less than 5 kilometres from the centre of town.

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Wotif suggests taking a squiz at the Holiday Inn Express Hotel & Suites Chestertown and Quality Suites if you intend to stay close to all the hustle and bustle.

With a varied program of exhibits and displays, you'll most definitely discover a thing or two that's up your alley at River Arts Chestertown. Two ideal hotel options near here include Driftwood Inn and John L Stam House.

For some alternatives, checkout the Historic Kent Manor Inn and the Hilton Garden Inn Kent Island. They are located 30 kilometres and 30 kilometres respectively from the center. Wotif also recommends the Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island. The first is 30 kilometres away from town, while the second is 30 kilometres away.

If you'd like to check out some close by localities, think about Rock Hall and Easton. Travel 16 kilometres to the southwest of Chestertown and you'll find Rock Hall. Alternatively, Easton is 50 kilometres to the south. Rock Hall hotels and apartments include the Mariners Motel and Inn at Osprey Point. The Tidewater Inn and Hampton Inn Easton are some of the ones in Easton.

Aussies are known internationally for their love of sport, so why not visit Ripken Stadium? Ripken Stadium is positioned to the north of Chestertown. Those wanting to stay close to the action can take their choice from the Residence Inn Aberdeen at Ripken Stadium and the Courtyard Aberdeen at Ripken Stadium.

If you are transiting into or out of Baltimore Washington International Thurgood Marshall Airport and looking to stay nearby, check out the latest deals at the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.

Chestertown hotels essential information

Accommodation
1,021 hotels
Lowest Price
AU$106
Highest Price
AU$597
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, Sagamore Pendry Baltimore, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie, Annapolis Waterfront Hotel, Autograph Collection, Quality Inn & Suites Bel Air I-95 Exit 77A, Hampton Inn Baltimore Bayview Campus

Frequently asked questions

What are the best hotels in Chestertown?
Located in Chestertown and with conveniences such as free internet services and high-speed internet services, Comfort Inn & Suites Chestertown is a retreat Wotif travellers are crazy about. Also securing a top spot on the list of best hotels in Chestertown is Red Roof Inn & Suites Chestertown. Get your shut-eye here and you’ll be near leading sights like Washington College and Garfield Centre for the Arts at the Prince Theatre. Ready for an amazing time in Chestertown? Let Wotif hook you up with an awesome pad at a rate that can’t be beat.
How many days should I spend in Chestertown?
Stay a few days, a few weeks or a lot longer — you do you. Start by working out the attractions you want to see as well as your preferred travel pace. Your budget will help you decide too. When you’re ready to lock in your Chestertown hotel and flight, we’ll help you make it happen.
Where should a first-time tourist stay in Chestertown?
Make life uncomplicated and book a hotel in Chestertown that’ll put you in the centre of the action. You’ll be close to things like top attractions and more transport options. Naturally, the best place to stay for you depends on things like your plans and budget, so do your homework before you go.
How much does a Chestertown hotel cost?
Chestertown hotel prices differ depending on when you plan to travel and just how swish you want your digs to be. To score AU$106 cheap accommodation in Chestertown, enter your details, click search, then filter your results by property class, budget, amenities and more. Another cost-saving tip? Avoid travelling during the busiest months of February, March and October, when rates are generally higher. Your inner bargain hunter will thank you for it.
How do I get a cheap hotel in Chestertown?
Get the lowdown on how to score cheap hotels in Chestertown with some of these tips and tricks:

  • Keep your budget in check by staying midweek: Cheaper room rates are typically offered from Mondays to Thursdays.
  • Pocket perks by joining Wotif: Unlock exclusive Mates Rates discounts, including 10% or more off select hotels, when you’re signed in to Wotif.
  • Travel outside of peak season: May, November and December are Chestertown’s least busy months when prices are at their lowest.
  • It’s all about the filters, dear traveller: Use our handy filter tool to narrow your search, then sort by the lowest price to find a hot deal.

Which hotels in Chestertown are family-friendly?
Our “Family friendly” filter is the simplest way to find family accommodation in Chestertown. With amenities and perks like games rooms, pools and playgrounds, your little ones will hit the fun jackpot while you score your dream getaway. It’s a win-win all round. A couple of our favourites are:


What is the best area to stay in Chestertown?
The neighbourhoods of Pomona and Edesville are two of our favourites. Whether it’s dining and entertainment districts you’re into, or more tranquil areas to get your holiday zen on in, we’ve got a Chestertown hotel with your name on it. Discover your ideal accommodation in Chestertown using our “View Map” feature at the top of the page. Happy hunting, dear traveller!

New reviews! Best hotels in Chestertown

Historic Inns of Annapolis
Wotif Verified Review
5 / 5
Beautiful hotel in the heart of the city. Everything was in walking distance. Nice staff. Loved the valet parking.
A verified traveller stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis

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