A boat docked at a pier during twilight with a city skyline in the background.

Search the Best Cabins in Chester

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Exterior

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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,010 reviews)
"Very clean hotel,beautiful view and great staff."
United States
Jackie
$118 nightly
The price is $131
Sep 1 - Sep 2
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (819 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
$167 nightly
The price is $185
Sep 8 - Sep 9
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Exterior

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,009 reviews)
"Nice 1 night stay"
United States
roney
$147 nightly
The price is $163
Aug 31 - Sep 1
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Exterior

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,006 reviews)
"good for a short stay"
United States
chanel
$119 nightly
The price is $132
Aug 31 - Sep 1
Total with taxes and fees
Best Western Kent Narrows Inn
Reception

5. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (179 reviews)
"Wonderful room, bar and food!"
United States
Leigh
$197 nightly
The price is $215
Sep 14 - Sep 15
Total with taxes and fees
Kent Island Resort
Exterior

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (957 reviews)
"Clean room and easy parking"
United States
Faezeh
$101 nightly
The price is $112
Sep 14 - Sep 15
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Front of property - evening/night

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (479 reviews)
"helpful staff, nice rooms"
United Kingdom
Jamie
$215 nightly
The price is $238
Sep 8 - Sep 9
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Front of property

8. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (518 reviews)
"Always clean staff friendly professional used to pretty much live here years ago always worked with me treated me right.Highly recommend 👌 👍"
United States
Stephen
$83 nightly
The price is $95
Aug 26 - Aug 27
Total with taxes and fees
Village Inn Annapolis MD
View from property

9. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very Good, (1,019 reviews)
"Room was pleasant and clean and breakfast was great!"
United States
Karen
$84 nightly
The price is $93
Sep 10 - Sep 11
Total with taxes and fees
St Michaels Inn
Garden

10. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,131 reviews)
"Great staff everywhere on the property."
United States
Fabiana
$98 nightly
The price is $111
Aug 30 - Aug 31
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Exterior

11. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,031 reviews)
"Good location, clean and quiet."
United States
Nelson
$106 nightly
The price is $121
Sep 7 - Sep 8
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
Exterior

12. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very Good, (1,010 reviews)
"Reasonable value for the money"
United States
Frank
$105 nightly
The price is $120
Aug 30 - Aug 31
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
Exterior

13. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (230 reviews)
"Great Location"
United States
Gary
$127 nightly
The price is $145
Aug 30 - Aug 31
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
Exterior

14. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,010 reviews)
"It had a wonderful breakfast and friendly staff"
United States
George
$80 nightly
The price is $91
Aug 30 - Aug 31
Total with taxes and fees
Best Western Annapolis
Exterior

15. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,016 reviews)
"We had an excellent stay. It was very clean and very conveniently located near everything we needed"
United States
Heather
$107 nightly
The price is $122
Sep 22 - Sep 23
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Exterior

16. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,978 reviews)
"Second time staying here and we love it!!"
United States
Stephanie
$159 nightly
The price is $181
Aug 26 - Aug 27
Total with taxes and fees
Historic Inns of Annapolis
Exterior

17. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,010 reviews)
"Nice place to stay friendly service"
United States
Glenn
$98 nightly
The price is $111
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Annapolis
Exterior

18. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$284 nightly
The price is $307
Aug 27 - Aug 28
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

19. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,006 reviews)
"Perfectly decent hotel for overnight stay during roadtrip."
United States
Phyllis
$92 nightly
The price is $105
Aug 31 - Sep 1
Total with taxes and fees
Courtyard by Marriott Annapolis
Exterior

20. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,076 reviews)
"Great stay"
United States
Leslie
$95 nightly
The price is $109
Sep 16 - Sep 17
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The beds were so comfortable"
christopher 1-night trip
Posted less than an hour ago
The Westin Annapolis

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
8,183
Accommodation
0 Cabin Rentals
Lowest Price
$91
Highest Price
$307

Frequently asked questions

What are the best cabins near Chester?
Rediscover the outdoors without roughing it at one of our 30 cabins in and around Chester. Whether you have adventure or relaxation on your mind, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay has plenty of both. Alternatively, spend your vacation at Country Coziness - Lancaster County Private Cabin and enjoy its beautiful natural surroundings.
Are there cheap cabins in Chester?
Priced from $91 to $307 a night, escaping the ordinary has never been easier. Book one of our cheap cabins in Chester and enjoy an adventure-filled vacation without blowing your budget.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 Chester?
Treat the youngsters to a vacation they won't forget in one of our Chester family cabins. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is a top option. It comes with loads of great amenities to make everyone comfortable, including a meal delivery service and a travel crib. Alternatively, create some wonderful new memories with the family at Country Coziness - Lancaster County Private Cabin. A deck and a toaster are just some of the things to take advantage of here.
What are the best river cabins near Chester?
When you think of the word peaceful, a river cabin near Chester should jump to mind. Cabin - - Picturesque Wooded Property With Unique Tiny House is one place where you can find some stillness. On top of its gorgeous surroundings, it features amenities such as on-site watersports and outdoor furniture. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another popular 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 Chester?
If you love the thought of every day being a pool day, make your way to Country Coziness - Lancaster County Private Cabin. It's one of our leading cabin rentals with a pool 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 leisurely days poolside. A swimming pool, a patio and good times are all guaranteed here.
What are some great Chester cabins?
When you want to spend time away in nature but aren't into wrestling with your pop-up tent, a cabin is a perfect solution. Book a few nights or more at Waterfront Ridge Retreat Cabin On St Jeromes Creek. This popular property comes with a water view, a deck and more. Alternatively, experience outdoor adventure and comfort combined at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. A firepit and a fireplace are among this escape's amenities.
What are the best weekend cabin rentals in Chester?
If you're eager to spend a couple of carefree days connecting with nature, Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay has your name on it. Bunk down here for a weekend and make use of amenities including a patio and a firepit. Another popular retreat is Country Coziness - Lancaster County Private Cabin. Offering a swimming pool, a patio and plenty of chill vibes, you'll go home feeling like a new person.
What are the best cabin prices in Chester?
Whether you're on a tight budget or want to treat yourself on your next trip away, you'll find what you're looking for on Expedia. At the moment, you can rent a Chester cabin from just $91 a night.
Can I find log cabins in Chester?
If you're pining for a more laid-back pace, you'll find it at one of our log cabins in Chester. For example, 1850 Historic Log Cabin. Spend your days here going boating and rafting and then return home to relax among its many comforts. Time also seems to slow right down at Tiny House / Log Cabin In Beautiful Wooded Urban Setting. When you're ready to explore beyond your cozy hideout, swimming and surfing opportunities are close by.
What are the highest-rated cabins in Chester?
With an impressive rating, it's easy to understand why Waterfront Ridge Retreat Cabin On St Jeromes Creek is a hit with Expedia adventurers. Some useful amenities here include a patio and a firepit. Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay is another fantastic choice. Conveniences like a patio and a firepit will help you feel right at home.
Why should I book a cabin in Chester?
For an escape that's big on charm, home comforts and affordability, a cabin is the way to go. Ditch your city blues for the greenery of the great outdoors. From days filled with exploring to cozy nights cuddled up by the fire, cabins offer both excitement and relaxation. You'll find the best Chester options on Expedia.
What are the top nature cabins in Chester?
Book a stay at Cabin - - Picturesque Wooded Property With Unique Tiny House and you'll be surrounded by breathtaking nature. Useful amenities such as a firepit and on-site watersports help make this river cabin in Chester a popular pick. Cabin - Vintage Waterfront A Frame - Hideaway On The Bay is another place where you can escape the city and simply laze by the river. Some of the conveniences here include on-site watersports and a fireplace.

Explore a world of travel with Expedia