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Check Chestertown hotel prices

Tonight
Jun 9 - Jun 10
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Jun 10 - Jun 11
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Jun 14 - Jun 16

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Top hotels and accommodation in Chestertown

Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, 679 reviews
"It was great"
The price is NZ$232
per night
27 Jun - 28 Jun
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, 277 reviews
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"
The price is NZ$147
per night
16 Jun - 17 Jun
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball, beach bar
The Lodge at Great Oak Landing
3.0 star property
7.6 out of 10, Good, 4 reviews
"The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time. "
The price is NZ$241
per night
10 Jun - 11 Jun
The Lodge at Great Oak Landing
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Driftwood Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, 160 reviews
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "
The price is NZ$115
per night
10 Jun - 11 Jun
Driftwood Inn
Inn at Huntingfield Creek
Lake
Inn at Huntingfield Creek
3.5 star property
10.0 out of 10, Exceptional, 44 reviews
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
The price is NZ$417
per night
20 Jun - 21 Jun
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, 85 reviews
"Really cute property and rooms. The rooms are small but exceptionally clean and nicely decorated. Pretty grounds with a pool, fire pit, hammocks and yard games available. Easy walking distance to a few restaurants. Staff was very pleasant. "
The price is NZ$303
per night
10 Jun - 11 Jun
Mariners Motel
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 18 reviews
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is NZ$441
per night
10 Jun - 11 Jun
BAYSIDE BUNGALOW
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$269
per night
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel cot, free WiFi, bed sheets
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, 76 reviews
"Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town."
Carriage House Hideaway in Middle of Chestertown
200 steps to the beach!
Interior
200 steps to the beach!
10.0 out of 10, Exceptional, 76 reviews
"House was beautifully decorated, updated, clean, and as advertised, steps from the beach!!! We had everything we needed for meal prep, including a charcoal grill. Enjoyed grilling fresh fish for dinner one night!"
200 steps to the beach!
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, 38 reviews
"This was our second stay at your lovely cottage. I’m sure it won’t be our last. Great location!"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Cute waterfront apartment -- 8 min from the beach!
Property grounds
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, 5 reviews
"I raced the Waterman's tri and this location was perfect, well equipped, comfortable, clean, easy."
Cute waterfront apartment -- 8 min from the beach!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, 77 reviews
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Waterfront Oasis w/ Private Dock, 3BR/2BA
Pool
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, 20 reviews
"The kids joined us for a weekend on our sailboat, this was the perfect spot to get together after a long day on the water. My one son set a new record on the PAC Man and the other caught a beautiful bass off the dock. The river view from the sunroom is spectacular! Everyone always migrated there. Great time had by all. We will be back in the fall."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Rambling Victorian Beach House on Maryland's Eastern Shore
Beach nearby, sun-loungers, beach towels
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 13 reviews
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
This is truly a Baydream!
Exterior
This is truly a Baydream!
10.0 out of 10, Exceptional, 28 reviews
"Very nice clean, comfortable house; quiet neighborhood."
This is truly a Baydream!
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, 1 review
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is NZ$683
per night
26 Jun - 27 Jun
Bayside Cottage steps from Rock Hall Harbor
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, 35 reviews
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, 27 reviews
"It was a great getaway for our church group!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Charming Chestertown Waterfront Cottage
Beach towels
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, 59 reviews
"This is a great place to relax. The house had everything we needed and was very comfortable."
Charming Chestertown Waterfront Cottage
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See all available properties in Chestertown
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.

More cheap accommodation in Chestertown

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

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

2112a Emmorton Park Road, Edgewood, MD
The price is NZ$111 per night from Jun 10 to Jun 11
NZ$111
per night
10 Jun - 11 Jun
7.2/10 Good! (1,010 reviews)

Stay near top Chestertown attractions

Image for Washington College

Washington College

Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

See properties
Washington College

Chestertown hotels information

Number of reviews
5,625
Accommodation
989 hotels
Lowest Price
NZ$111
Highest Price
NZ$683

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite 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 stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. See all vacation rentals in Chestertown.

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

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, 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.

What's the best accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers 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 family accommodation 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 stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best place to stay for couples in Chestertown?

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

What is the top LGBTQ-friendly hotel 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 two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best dog-friendly accommodation option in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a fitness centre and laundry facilities for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

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

The Lodge at Great Oak Landing is a top lodge located on the beach . Great Oak Manor is another good option to stay near the beach. See more stays near the beach in Chestertown.

What's the best hotel in Chestertown to learn about 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. See more options for historical stays in Chestertown.

What are some accommodation options with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, a private beach and 3 bars/lounges. 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 centre. See all spa hotels in Chestertown.

Recent Reviews in Chestertown
Expedia verified reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

5/5 Excellent
"Great stay!"
A verified traveller from Glen Burnie stayed at Hampton Inn Baltimore/Glen Burnie
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie