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Search the Best Cabins in Chester

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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, (1,000 reviews)
"Good hotel for the money and location."
United States
Marc
$110 nightly
The price is $122
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A multi-story hotel with outdoor seating areas and a dock extending into the water.

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (841 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
$152 nightly
The price is $169
Oct 18 - Oct 19
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A Hilton Garden Inn with a marina view, featuring a large building with a prominent logo, a covered entrance, and a parking lot.

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice 1 night stay"
United States
roney
$139 nightly
The price is $154
Oct 19 - Oct 20
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, (1,000 reviews)
"Everyone was pleasant but the hotel was older and fairly expensive for the quality and look of the hotel. It was a motel at one point."
United States
Beth
$108 nightly
The price is $120
Oct 14 - Oct 15
Total with taxes and fees
Best Western Kent Narrows Inn
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

5. 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, (499 reviews)
"Great property super friendly, helpful staff."
United States
scott
$214 nightly
The price is $238
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (986 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
$96 nightly
The price is $107
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A large, two-story barn-style building with a covered front porch and a garage.

7. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (187 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
$154 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Kent Island Resort
A historic brick building with a red roof, multiple windows, and a central staircase.

8. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,038 reviews)
"Would stay again"
United States
Ashley
$125 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Historic Inns of Annapolis
A marina with boats docked, a white building with a flat roof, and a white car parked in a lot.

9. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
Cass-N-Reel Luxury Houseboat
A modern hotel with a symmetrical facade, large windows, and a well-lit entrance.

10. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (244 reviews)
"Nice hotel"
United States
Imola
$101 nightly
The price is $115
Oct 13 - Oct 14
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

11. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,235 reviews)
"My favorite place to stay in Annapolis"
United States
Michele
$90 nightly
The price is $103
Oct 12 - Oct 13
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A hotel with a modern facade, multiple entryways, and a prominent sign.

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"Loved everything about it but especially the staff was so friendly and accommodating!"
United Kingdom
petra
$106 nightly
The price is $121
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
A building with a covered porch supported by columns, a garage with a parked truck, and a small garden with flowers.

13. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,000 reviews)
"Great location close to downtown."
United States
Lynn
$99 nightly
The price is $109
Oct 11 - Oct 12
Total with taxes and fees
St Michaels Inn
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$291 nightly
The price is $314
Oct 14 - Oct 15
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
A brick building with a large entrance and a sign reading "Graduate Annapolis."

15. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,005 reviews)
"Great Hotel in a very central location"
United States
Mark
$147 nightly
The price is $167
Oct 26 - Oct 27
Total with taxes and fees
Graduate by Hilton Annapolis
Front of property

16. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (526 reviews)
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
United States
Keith
$83 nightly
The price is $95
Oct 12 - Oct 13
Total with taxes and fees
Village Inn Annapolis MD
A hotel with a covered entrance, large columns, and a brick facade.

17. 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, (1,000 reviews)
"We stayed for 3 nights and we had a good experience."
Canada
Omer
$110 nightly
The price is $125
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

18. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,006 reviews)
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
United States
Silvia
$80 nightly
The price is $91
Oct 12 - Oct 13
Total with taxes and fees
Best Western Annapolis
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

19. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
$178 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
Inn at Huntingfield Creek
A Hilton Garden Inn with a large building and a smaller entrance building.

20. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,000 reviews)
"Nice place to stay friendly service"
United States
Glenn
$101 nightly
The price is $115
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis
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.
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Top Chester Hotel Reviews

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"clean room. small bathroom but clean. wi-fi good. breakfast was good. staff helpful. overall, a good stay for one night. walkable area - close to a shopping area."
Catharina 1-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Annapolis by IHG

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
10,085
Accommodation
0 Cabin Rentals
Lowest Price
$91
Highest Price
$314

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 $314 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.

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