15 Best Cabins in Chestertown, MD - Cabins for Rent from $70

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

$103 nightly

Oct 4 - Oct 5

Total with taxes and fees

2. The Lodge at Great Oak Landing

Chestertown

Lynda

$122 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Red Roof Inn & Suites Chestertown

Chestertown

Linda

$71 nightly

Sep 30 - Oct 1

Total with taxes and fees

4. Driftwood Inn

Chestertown

Vanesa

$64 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

$144 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

$319 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Chestertown

$270 nightly

Oct 5 - Oct 6

Total with taxes and fees

8. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

$271 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Chestertown

Mandy D.

$478 nightly

Sep 7 - Sep 8

Total with taxes and fees

10. Haven Point Inn and Gallery

Rock Hall

John

$127 nightly

Oct 6 - Oct 7

Total with taxes and fees

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

Millington

Riley B.

$118 nightly

Sep 10 - Sep 11

Total with taxes and fees

12. Inn at Huntingfield Creek

Rock Hall

Christine

$200 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Rock Hall

lisa p.

$261 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Grasonville

Emily

$119 nightly

Oct 5 - Oct 6

Total with taxes and fees

15. BAYSIDE BUNGALOW

Rock Hall

Diane V.

$260 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Bel Air

Tatsiana

$90 nightly

Sep 20 - Sep 21

Total with taxes and fees

17. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

Eileen

$98 nightly

Oct 4 - Oct 5

Total with taxes and fees

18. Best Western Kent Narrows Inn

Grasonville

Joshua

$116 nightly

Sep 28 - Sep 29

Total with taxes and fees

19. Hilton Garden Inn Bel Air

Bel Air

michelle

$114 nightly

Sep 20 - Sep 21

Total with taxes and fees

20. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

$152 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Chestertown Hotel Reviews

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."

Historic Inns of Annapolis

8/10 Good

"I liked the archaeological displays and the historically preserved property. The room was very comfortable. Some of the front desk staff were not very friendly. Some of the parking attendants were often seen glued to their cell phones rather than offering assistance. The valet online service was inconvenient and too expensive. I wanted to leave an online gratuity but did not like the convenience fee charged!"

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	$70
Highest Price	$497

Frequently asked questions

What are the best cabins near Chestertown?

Rediscover the great outdoors without giving up the comforts at one of our 33 cabins in and around Chestertown. Whether you have relaxation or fun on your itinerary, Cozy Cabin Happiness has lots of both. Alternatively, get cozy at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay and enjoy staring out at its wonderful natural surroundings.

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 $70 to $497 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?

Treat the youngsters to their best vacation yet in one of our Chestertown family cabins. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a top pick. It comes with loads of amenities to make you and your gang feel right at home, including a meal delivery service and a travel crib. Or you can create some marvelous new memories together at Country Coziness - Lancaster County Private Cabin. A deck and a toaster are some of the conveniences to take advantage of here.

What are the best river cabins near Chestertown?

Spend your days kicking back near the water and your evenings listening to it trickling past at a river cabin near Chestertown. Leading our list is Cabin - - Picturesque Wooded Property With Unique Tiny House. This riverside property comes with on-site watersports and outdoor furniture. Or, spend your break at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Along with its picturesque location, highlights here include on-site watersports and a firepit.

What are the best cabins with pools near Chestertown?

Put on your swimwear and enjoy a relaxing dip whenever the mood strikes when you select one of our cabin rentals with a pool. Country Coziness - Lancaster County Private Cabin is a favorite. A swimming pool and a patio are some of the other amenities that'll help make your stay comfortable. Or you can spend your getaway at Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay. As well as a lovely pool, this cabin comes with a swimming pool and a patio.

What are some great Chestertown cabins?

When you want to spend your vacation surrounded by nature but don't feel like roughing it, a cabin is a smart choice. Escape to Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This top pick comes with a firepit, a fireplace and more. Alternatively, experience comfort and outdoor fun at the same time at Pet - Friendly Lakeview Cabin W. A deck and a dock are among this retreat's amenities.

What are the best weekend cabin rentals in Chestertown?

Whether you're planning a mini break with your other half or your close friends, we'll help you locate the perfect weekend cabin getaway. One of our favorites? Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. Featuring a patio and a firepit, you'll adore being close to nature here. Country Coziness - Lancaster County Private Cabin is another good place where you can hit pause on life. Enjoy a few nights at this escape which offers a swimming pool and a patio.

Can I find log cabins in Chestertown?

Begin your day with a hot coffee in your cozy log cabin and then go shore fishing and boating. Sound like your dream vacation? Head for 1850 Historic Log Cabin. Another relaxing retreat offering ample charm and comforts is Log Cabin In Townsend Delaware. Close-by activities like stand-up paddle boarding and shore fishing will add to the good times here.

What are the highest-rated cabins in Chestertown?

There are some places that are great in every way. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is one of them. With such an impressive rating, it comes with useful amenities like a patio, a firepit and more. Another excellent option is Pet - Friendly Lakeview Cabin W. A patio and a firepit are just a couple of the conveniences you'll find 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?

Affordability, outdoor activities, rustic charm — there's no end of good reasons to choose a Chestertown cabin. Leave behind the clamor of the concrete jungle and rise with the sound of songbirds and wildlife. There's so much adventure just around the corner too. Whether you're vacationing with family members, friends or your sweetheart, you'll discover the perfect rental cabin on Expedia.

What are the top nature cabins in Chestertown?

Our nature cabins in Chestertown come in many shapes and budgets, but there's one thing they all share — unparalleled access to the great outdoors. Cabin - - Picturesque Wooded Property With Unique Tiny House is a magnet for nature lovers. Amenities such as a spa tub and a firepit only make it more appealing. Whether you want to get your feet moving or just put them up, do it at Cabin - Vintage Waterfront A Frame - Hideaway On The Bay. Another great option, it comes with on-site watersports and a patio.

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Chestertown Vacation Rentals

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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

Red Roof Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Cabin Rentals information

Frequently asked questions

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