Top Chestertown Cabin Rentals

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

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Recommended hotels in Chestertown

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

CA $159 total

includes taxes & fees

Oct 4 - Oct 5

2. The Lodge at Great Oak Landing

Chestertown

Lynda

CA $168 total

includes taxes & fees

Sep 27 - Sep 28

3. Red Roof Inn & Suites Chestertown

Chestertown

Linda

CA $111 total

includes taxes & fees

Sep 13 - Sep 14

4. Driftwood Inn

Chestertown

Vanesa

CA $98 total

includes taxes & fees

Sep 7 - Sep 8

5. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

CA $220 total

includes taxes & fees

Sep 7 - Sep 8

6. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

CA $484 total

includes taxes & fees

Sep 7 - Sep 8

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

CA $397 total

includes taxes & fees

Oct 5 - Oct 6

8. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

CA $388 total

includes taxes & fees

Sep 7 - Sep 8

9. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

CA $666 total

includes taxes & fees

Sep 8 - Sep 9

10. Haven Point Inn and Gallery

Rock Hall

John

CA $179 total

includes taxes & fees

Oct 6 - Oct 7

11. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

CA $173 total

includes taxes & fees

Sep 10 - Sep 11

12. Inn at Huntingfield Creek

Rock Hall

Christine

CA $277 total

includes taxes & fees

Sep 13 - Sep 14

13. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

CA $403 total

includes taxes & fees

Sep 7 - Sep 8

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

Grasonville

Emily

CA $183 total

includes taxes & fees

Oct 5 - Oct 6

15. BAYSIDE BUNGALOW

Rock Hall

Diane V.

CA $402 total

includes taxes & fees

Sep 11 - Sep 12

16. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

Tatsiana

CA $140 total

includes taxes & fees

Sep 20 - Sep 21

17. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

Eileen

CA $151 total

includes taxes & fees

Oct 4 - Oct 5

18. Best Western Kent Narrows Inn

Grasonville

Joshua

CA $179 total

includes taxes & fees

Sep 28 - Sep 29

19. Hilton Garden Inn Bel Air

Bel Air

michelle

CA $181 total

includes taxes & fees

Sep 27 - Sep 28

20. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

CA $233 total

includes taxes & fees

Oct 4 - Oct 5

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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

8/10 Good

"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."

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

10/10 Excellent

"This hotel was actually better than I expected. Check-in was quick and easy. Lots of parking. My room on the 5th floor was spacious and super clean. The beds and pillows were great! The breakfast buffet was adequate. Overall, a good stay and I’d stay there again.,"

Red Roof Inn & Suites Chestertown

10/10 Excellent

"Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating."

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

8/10 Good

"Front desk pleasant and helpful, but… no accessible rooms available. Also, only non pet room available (even though reservations were made) was on 2nd floor and elevator out of service. Room itself was clean. Breakfast was good."

Best Western Plus Hotel & Conference Center

10/10 Excellent

"Multiple Elevators were out of service and had longer wait for available one to use. Buttons seemed to not work in that one elevator that was working and light kept going out for the floor I needed to be and kept stopping one floor below instead. But staff were so kind and friendly. Very helpful staff with information in area, shuttle information and very welcoming. I did enjoy staying and if coming to Baltimore again, I will choose to stay here again. Hope the elevator will be in good condition by the time I go back."

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews	3,448
Accommodation	4 Cabin Rentals
Lowest Price	CA $98
Highest Price	CA $666

Frequently asked questions

What are the best cabins near Chestertown?

Book one of our 33 cabins in Chestertown and you'll be rewarded with picturesque scenery, outdoor adventure and memories you'll never forget. Cozy Cabin Happiness is the place to go for a relaxing getaway. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is also ideal if you'd love some time out in Mother Nature.

Are there cheap cabins in Chestertown?

For a budget-friendly escape in nature, look no further than our cheap cabins in Chestertown. Wake up in the morning to the sweet sound of birds chirping from one of our cozy retreats priced from CA $98 to CA $666 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best family cabins near Chestertown?

If you're seeking a getaway the kids will go wild for, a family cabin rental in or near Chestertown is ideal. Spend time with the gang at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. It offers a meal delivery service and a travel crib as well as ample outdoor adventure. Country Coziness - Lancaster County Private Cabin is another top pick for small groups or families and comes with a deck and a toaster.

What are the best river cabins near Chestertown?

When you think of the word relaxing, a river cabin near Chestertown should be the first thing that comes to mind. Cabin - - Picturesque Wooded Property With Unique Tiny House is the perfect place to discover your Zen. On top of its beautiful surroundings, it features amenities such as on-site watersports and outdoor furniture. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another appealing option. On-site watersports and a firepit are a few of the conveniences that await you here.

What are the best cabins with pools near Chestertown?

If you love the thought of every day being a pool day, escape to Country Coziness - Lancaster County Private Cabin. It's one of our leading cabin rentals with a pool near Chestertown and comes with handy amenities like a swimming pool and a patio. Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay is another fantastic place to spend your days splashing around. A swimming pool, a patio and good times are all on the menu here.

What are some great Chestertown cabins?

From chic pads with all the fancy perks to cozy retreats that are easy on the hip pocket, Expedia has cabin rentals to suit every taste and budget. Spend a few days enjoying Mother Nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Conveniences here include a firepit and a fireplace. Another excellent option is Pet - Friendly Lakeview Cabin W. It features a deck, a dock and more.

What are the best weekend cabin rentals in Chestertown?

Nothing's as good as a weekend cabin getaway after a tiring week at work. Ditch your cubicle for a few days in nature at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. A patio and a firepit are among the amenities it offers. Emails will also be the furthest thing from your mind at Country Coziness - Lancaster County Private Cabin. Put your bags down here and make the most of a swimming pool and a patio.

What are the best cabin prices in Chestertown?

With prices starting at just CA $98 a night for a cabin rental in Chestertown, there's no need to wrestle with that hard-to-pitch tent.

Can I find log cabins in Chestertown?

Kick off your day with a hot coffee in your peaceful log cabin and then try some surfing and swimming. Sound perfect to you? Book a stay at 1850 Historic Log Cabin. Another getaway that comes with lots of character and comfort is Log Cabin In Townsend Delaware. Nearby activities like sea kayaking and hiking will add to the good times here.

What are the highest-rated cabins in Chestertown?

There are some cabin stays that are just about perfect. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a prime example. With an impressive rating, it comes with useful amenities such as a patio, a firepit and loads more. Another terrific option is Pet - Friendly Lakeview Cabin W. A patio and a firepit are a few of the conveniences you'll appreciate here.

What are the top things to see and do in Chestertown?

If you're looking to do some sightseeing around Chestertown, don't miss Washington College. Feeling adventurous? Pick up a car rental and find your way to attractions a little farther out, including Rolphs Wharf Marina. There's an amazing world to enjoy beyond your comfortable cabin!

Why should I book a cabin in Chestertown?

For a vacation in the great outdoors at an amazing price, there's nothing better than a cabin. Imagine rising to the sound of birds outside and sipping coffee on a private deck surrounded by stunning vistas. Stay in a cabin in Chestertown to get away from the hectic pace of the city. Whether they're by the beach, in the mountains or near a river, cabins offer a rustic and relaxing experience you'll always remember.

What are the top nature cabins in Chestertown?

Stay at Cabin - - Picturesque Wooded Property With Unique Tiny House and you'll be surrounded by breathtaking nature. Amenities such as on-site watersports and a firepit help make this river cabin in Chestertown a popular choice. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another place where you can escape the concrete jungle and unwind by the river. Conveniences here include on-site watersports and a patio.

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Find Cabins in Chestertown for Rent from CA $98

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Chestertown

1. Comfort Inn & Suites Chestertown

2. The Lodge at Great Oak Landing

3. Red Roof Inn & Suites Chestertown

4. Driftwood Inn

5. First Floor Studio Apartment in Historic Chestertown

6. Newly restored apartment in the heart of Chestertown

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

8. Secluded Cottage in Middle of Chestertown

9. Wren Retweet- Country Estate in Center of C’Town

10. Haven Point Inn and Gallery

11. Guest Suite for up to 2 in a Victorian on the Chester River

12. Inn at Huntingfield Creek

13. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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

15. BAYSIDE BUNGALOW

16. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

17. Home2 Suites by Hilton Baltimore / Aberdeen, MD

18. Best Western Kent Narrows Inn

19. Hilton Garden Inn Bel Air

20. Hyatt Place Kent Narrows & Marina

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cabin Rentals information

Frequently asked questions

Explore a world of travel with Expedia