Photo by Patricia Knorr

Find 2 Star Hotels in Chester, MD from $87

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Compare Chester 2 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Chester 2-star hotels

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1000)
"Very nice property new rooms "
$86 nightly
The price is $99
Sep 11 - Sep 12
Total with taxes and fees
Best Western Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very Good, (1016)
"Very nice hotel and exactly what I needed for the night. "
$111 nightly
The price is $126
Sep 15 - Sep 16
Total with taxes and fees
Hampton Inn & Suites Annapolis

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (108)
"Great stay"
$103 nightly
The price is $117
Sep 8 - Sep 9
Total with taxes and fees
Candlewood Suites Annapolis by IHG

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1000)
"Excellent location"
$109 nightly
The price is $121
Sep 10 - Sep 11
Total with taxes and fees
Best Western Kent Narrows Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (779)
"Always look forward to our stay here on our way to the ocean. It’s part of our yearly plan. "
$85 nightly
The price is $94
Oct 1 - Oct 2
Total with taxes and fees
Quality Inn

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (365)
"Fantastic place for a couple getaway. "
$259 nightly
The price is $285
Sep 9 - Sep 10
Total with taxes and fees
The Wildset

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Nice comfortable stay."
$129 nightly
The price is $142
Sep 4 - Sep 5
Total with taxes and fees
Best Western Plus Easton Inn & Suites

Quality Inn

2.5 star property
7.8 out of 10, Good, (820)
"Great place and great staff"
$98 nightly
The price is $108
Sep 17 - Sep 18
Total with taxes and fees
Quality Inn

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1000)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
$114 nightly
The price is $130
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1003)
"Great place to stay"
$90 nightly
The price is $100
Oct 1 - Oct 2
Total with taxes and fees
St Michaels Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (895)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
$131 nightly
The price is $145
Sep 14 - Sep 15
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (384)
"I liked the landscaping, the greeting of the lobby staff upon check in, and 2 staff members in the lobby when checking out. The room was very nice and quiet. I am very pleased with this hotel. Thank you for making my stay great."
$76 nightly
The price is $87
Sep 11 - Sep 12
Total with taxes and fees
Red Roof Inn Annapolis

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (68)
"Good service and good options to enjoy the stays. "
$209 nightly
The price is $230
Sep 18 - Sep 19
Total with taxes and fees
Wylder Tilghman Island

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (532)
"Check in staff is very helpful"
$139 nightly
The price is $152
Sep 14 - Sep 15
Total with taxes and fees
Hampton Inn Easton

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (358)
"Great place! "
$161 nightly
The price is $177
Sep 8 - Sep 9
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (448)
"The staff specifically Victoria was impeccable! "
$179 nightly
The price is $204
Sep 4 - Sep 5
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina

Village Inn

2.0 star property
6.2 out of 10, (493)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
$89 nightly
The price is $102
Sep 8 - Sep 9
Total with taxes and fees
Village Inn

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (373)
"The staff was VERY nice"
$86 nightly
The price is $94
Sep 10 - Sep 11
Total with taxes and fees
Econo Lodge Easton Route 50

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"Very friendly staff!"
$213 nightly
The price is $243
Sep 8 - Sep 9
Total with taxes and fees
134 Prince - Luxury Boutique Hotel

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
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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.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

Chester Motel Guide

Planning a getaway with only a few bucks to spare? Expedia can help! With the inexpensive rates at the top motels in Chester, Maryland you can put together the vacation of your dreams without spending every penny of your yearly travel budget.

These smaller places are ideal if you need a home base that lets you easily explore the local sights; many of the best motels in Chester are located near major freeways and public transportation. Plus, when you book a cheap deal on a motel in Chester, you’ll find quiet rooms, complimentary toiletries, and comfortable sleeping areas, so you can unwind after a long day.

No matter which motel you choose, don't forget to use the travel tools at Expedia to search for local discounts, compare rates on the hottest motels, and plan your next vacation. You won't believe how budget-friendly an amazing getaway can be.

Also, feel free to check out the motels near me page to find the cheapest deals on motels near your current location.

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Explore a world of travel with Expedia