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Search the Best Cabins in Chester

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Dec 19 - Dec 21
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Dec 26 - Dec 28
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Jan 9 - Jan 11
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No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
$81 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn
Exterior
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (862)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
$85 nightly
The price is $94
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
"Great place!"
United States
Tawnya
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Restaurant
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
$175 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
Wylder Tilghman Island
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
$109 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Easton
Front of property
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
$120 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Knapps Narrows Marina & Inn
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1004)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
$71 nightly
The price is $81
Dec 28 - Dec 29
Total with taxes and fees
Best Western Annapolis
Exterior
Country Inn & Suites by Radisson, Annapolis, MD

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, (1003)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
$95 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
View from property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
$105 nightly
The price is $116
Dec 24 - Dec 25
Total with taxes and fees
St Michaels Inn
Exterior
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (165)
"Beautiful and very modern, breakfast was great"
United States
Dominic
$110 nightly
The price is $125
Dec 18 - Dec 19
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
Meeting facility
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (841)
"Friendly staff, spotless room, great location. "
United States
Steven
$179 nightly
The price is $197
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Tidewater Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$179 nightly
The price is $195
Dec 16 - Dec 17
Total with taxes and fees
Kent Island Resort
Exterior
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room and friendly staff! "
United States
Silvia
$80 nightly
The price is $91
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1001)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
$129 nightly
The price is $142
Dec 14 - Dec 15
Total with taxes and fees
Best Western Plus Easton Inn & Suites
Exterior
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
$74 nightly
The price is $84
Dec 22 - Dec 23
Total with taxes and fees
Hilton Garden Inn Annapolis
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
$149 nightly
The price is $170
Dec 28 - Dec 29
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Exterior
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$83 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (180)
"Nice staff, clean room, comfortable bed. "
United States
Jayne
$84 nightly
The price is $96
Dec 19 - Dec 20
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Property grounds
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (58)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
$144 nightly
The price is $160
Dec 15 - Dec 16
Total with taxes and fees
Inn at Huntingfield Creek
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Courteous and helpful staff. Very clean. "
Lisa 4-night trip
Posted 18 hours ago
Hilton Garden Inn Annapolis Downtown

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
13,485
Accommodation
1 Cabin Rentals
Lowest Price
$81
Highest Price
$197

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 $81 to $197 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 $81 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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