Photo by Patricia Knorr

Find 2 Star Hotels in Chester, MD from $56

Start date: Check-in selected.
To Date
End date: Check-out

    Upfront pricing

    Our total price for your stay includes taxes and fees

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

    Be picky

    Search almost a million properties worldwide

Check availability on Chester 2 Star Hotels

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

Exterior
Best Western Annapolis
Best Western Annapolis
2.5 star property
7.8 out of 10, Good, (1015)
"Clean room, nice staff and plenty of parking "
$76 nightly
The price is $86
Nov 16 - Nov 17
Total with taxes and fees
Best Western Annapolis
Front of property
St Michaels Inn
St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, (1000)
"Great location, free parking, free breakfast excellent staff."
$93 nightly
The price is $103
Oct 22 - Oct 23
Total with taxes and fees
St Michaels Inn
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
8.2 out of 10, Very Good, (1009)
"We had a nice stay. "
$95 nightly
The price is $108
Oct 29 - Oct 30
Total with taxes and fees
Hampton Inn & Suites Annapolis
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (841)
"Great place and great staff"
$96 nightly
The price is $107
Nov 16 - Nov 17
Total with taxes and fees
Quality Inn
Exterior
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
2.5 star property
8.8 out of 10, Excellent, (142)
"This hotel was a nice surprise tucked away in a quiet area, yet close to everything Annapolis has to offer. The woman who checked us in was very welcoming and helpful!"
$97 nightly
The price is $111
Oct 28 - Oct 29
Total with taxes and fees
Candlewood Suites Annapolis by IHG
Exterior
Quality Inn
Quality Inn
2.5 star property
7.6 out of 10, Good, (798)
"Everything was clean; staff friendly; breakfast great"
$85 nightly
The price is $94
Oct 23 - Oct 24
Total with taxes and fees
Quality Inn
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very Good, (1000)
"Clean room and good location to biking trail."
$92 nightly
The price is $102
Nov 16 - Nov 17
Total with taxes and fees
Best Western Kent Narrows Inn
Standard Room, 2 Double Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets
Red Roof Inn Annapolis
Red Roof Inn Annapolis
2.0 star property
7.2 out of 10, Good, (399)
"Unfortunately, I did wake up with a cockroach stuck to my arm. The hotel looked as if it was used in a horror film. If it was not in the area it is now, I wouldn’t have felt fully safe here. However, the staff was nice."
$78 nightly
The price is $89
Oct 19 - Oct 20
Total with taxes and fees
Red Roof Inn Annapolis
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
$111 nightly
The price is $123
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, (1002)
"Excellent staff, very clean room, good hotel breakfast "
$119 nightly
The price is $131
Nov 9 - Nov 10
Total with taxes and fees
Best Western Plus Easton Inn & Suites
Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets
Days Inn by Wyndham Easton
Days Inn by Wyndham Easton
2.5 star property
5.6 out of 10, (904)
"It was ok"
$51 nightly
The price is $56
Nov 2 - Nov 3
Total with taxes and fees
Days Inn by Wyndham Easton
Reception
Village Inn Annapolis MD
Village Inn Annapolis MD
2.0 star property
6.2 out of 10, (504)
"The room was very nice, clean and quiet. Great location"
$83 nightly
The price is $95
Nov 2 - Nov 3
Total with taxes and fees
Village Inn Annapolis MD
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi
The Wildset
The Wildset
2.5 star property
9.8 out of 10, Exceptional, (389)
"fantastic location, great bouboun selection at the bar and wonderful staff"
$239 nightly
The price is $263
Oct 28 - Oct 29
Total with taxes and fees
The Wildset
Exterior
Hampton Inn Easton
Hampton Inn Easton
2.5 star property
9.0 out of 10, Wonderful, (540)
"I’ve been travel for so many locations but this hotel was the best place I ever had so far staffing very politely and friendly and the free breakfast deserves my best appreciation. "
$136 nightly
The price is $150
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn Easton
Front of property
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (463)
"Property was very nice. They only downside was a limited breakfast."
$179 nightly
The price is $204
Oct 20 - Oct 21
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
8.2 out of 10, Very Good, (1001)
"Great location. "
$99 nightly
The price is $113
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express & Suites Annapolis by IHG
Free continental breakfast
Econo Lodge Easton Route 50
Econo Lodge Easton Route 50
2.5 star property
6.6 out of 10, (377)
"Was the best price hotel I found, but traffic is right close to my room. So it's a bit noisy but room and staff are nice. I would come back again. Noise is the only reason I gave mostly 4 stars. But different room may be less noise."
$81 nightly
The price is $89
Oct 23 - Oct 24
Total with taxes and fees
Econo Lodge Easton Route 50
View from property
Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott Easton
2.5 star property
9.6 out of 10, Exceptional, (363)
"Great hotel, very clean & quiet. "
$148 nightly
The price is $163
Nov 16 - Nov 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
Seasonal outdoor pool
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
8.8 out of 10, Excellent, (84)
"Very relaxing stay."
$211 nightly
The price is $232
Oct 23 - Oct 24
Total with taxes and fees
Wylder Tilghman Island
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
$282 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
134 Prince - Luxury Boutique Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Chester.
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle, Annapolis, MD
$145 nightly
The price is $166 total per night from Nov 2 to Nov 3
$166 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,846 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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!

See all hotels in Chester
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

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.

Explore a world of travel with Expedia