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Independent in Chestertown

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Featured Chestertown Independent

The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4 out of 5
180 Pier One Road, Stevensville, MD
Fully refundableReserve now, pay when you stay
Stay at this 4-star spa hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
The Inn at Chesapeake Bay Beach Club
Vandiver Inn
Vandiver Inn
3.5 out of 5
301 South Union Avenue, Havre De Grace, MD
Stay at this 3.5-star business-friendly B&B in Havre De Grace. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Vandiver Inn
Kent Island Resort
Kent Island Resort
3.5 out of 5
500 Kent Manor Dr, Stevensville, MD
Fully refundable
Book a stay at this golf hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Kent Island Resort
Relax Inn Smyrna
Relax Inn Smyrna
2 out of 5
1648 S Dupont Blvd, Smyrna, DE
Stay at this hotel in Smyrna. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Relax Inn Smyrna
Flag House Inn
Flag House Inn
3.5 out of 5
26 Randall St, Annapolis, MD
Stay at this 3.5-star B&B in Annapolis. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Popular attractions John Smith House and Annapolis City ...
Flag House Inn
Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Fully refundableReserve now, pay when you stay
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
Driftwood Inn
Naomi Bed & Breakfast
Naomi Bed & Breakfast
3 out of 5
9907 Harford Rd, Parkville, MD
Stay at this 3-star B&B in Parkville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions White Marsh Mall and Hampton National Historic Site ...
Naomi Bed & Breakfast
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 out of 5
134 Prince George St, Annapolis, MD
Stay at this hotel in Annapolis. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Popular attractions Annapolis City Dock and John Smith House ...
134 Prince - Luxury Boutique Hotel
Mariners Motel
Mariners Motel
2 out of 5
5681 South Hawthorne Avenue, Rock Hall, MD
Fully refundableReserve now, pay when you stay
Stay at this motel in Rock Hall. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Rock Hall Harbor and Waterman’s Museum are located ...
Mariners Motel
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool.
The Lodge at Great Oak Landing
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 out of 5
4928 Eastern Neck Rd, Rock Hall, MD
Stay at this 3.5-star spa B&B in Rock Hall. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Rock Hall Harbor and The Mainstay are ...
Inn at Huntingfield Creek
White Marsh Motel
White Marsh Motel
2 out of 5
11131 Pulaski Highway, White Marsh, MD
Stay at this motel in White Marsh. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Freestate Gun Range and White Marsh Mall are ...
White Marsh Motel
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.

Independent hotels in Chestertown

You’ve already taken the guesswork out of your next vacation. You know you want a Independent hotel in Chestertown. What can you say? You like their style, they’re in a good part of Chestertown, and they never let you down. New bar in town? You’re the first one to check it out. Spiciest item on the menu? You can take the heat. But even the best gamblers hedge their bets. No matter how crazy good your trip is, you want something familiar waiting for you at the end of the day.

All in a name

We all have favorites. There’s nothing wrong with knowing what you like. You like to stay at Independent near , Chestertown to do the tourist thing (because sometimes it is fun) and then hit up the places that aren’t on the map. And no matter what fun you get into, you have Independent hotels with their comfy beds and thoughtful amenities waiting to tuck you in.

As you like it

Have a price you want to stick to, so you can paint the town red? Maybe, it’s all about the hotel features. Who couldn’t use a hot tub? Pick your pleasure by:

  • Hotwire Hot Rate: Grab the Independent hotel in Chestertown at an absolute steal. After you book it, we’ll tell you the hotel name. You might nab that 4-star hotel for a 2-star price.
  • Price: How low can we go? Quite low in fact. Check out our prices per night, starting at $69.
  • Amenities: Grab a cocktail at the lounge and maybe wander upstairs to the rooftop terrace—all the stuff that makes a great vacay.

You’ve already done the hard part—figuring out where you want to stay. Now it’s time to use the money you saved to let the real fun begin. Underground shows? Off-beat attractions? Rooftop escapes? The choice is yours. The only thing wonderfully predictable about this trip is the Independent room you’ll be staying in.