Compare Cheap Hotels in Sherwood

Secret Bargains - Save an extra 10% or more on select hotels

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

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cheap Sherwood Hotels

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$164 nightly
The price is $187 total per night
$187 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.62 mi from city center
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Pet friendly
Free WiFi
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$76 nightly
The price is $87 total per night
$87 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.5 mi from city center
With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta Kinte Alex Haley Memorial.
Pet friendly
Parking included
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
$178 nightly
The price is $203 total per night
$203 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.32 mi from city center
With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and William Paca House.
Pet friendly
Free WiFi
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$114 nightly
The price is $130 total per night
$130 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Free Cancellation
19.68 mi from city center
Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical Center.
Pool
Parking included
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
$79 nightly
The price is $90 total per night
$90 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.81 mi from city center
With a stay at Hilton Garden Inn Annapolis Downtown, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
Pet friendly
Free WiFi
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$127 nightly
The price is $144 total per night
$144 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.79 mi from city center
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
Pet friendly
Free WiFi
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
$91 nightly
The price is $104 total per night
$104 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.25 mi from city center
With a stay at Sonesta ES Suites Annapolis in Edgewater, you'll be in the historical district, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Pool
Breakfast included
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
$175 nightly
The price is $199 total per night
$199 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.07 mi from city center
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Meredith House.
On private beach
Pool
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
$154 nightly
The price is $176 total per night
$176 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.89 mi from city center
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill Cemetery.
Pool
Spa
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr Annapolis MD
$94 nightly
The price is $107 total per night
$107 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.25 mi from city center
With a stay at Hampton Inn & Suites Annapolis in Annapolis, you'll be in the business district, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
$138 nightly
The price is $151 total per night
$151 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.54 mi from city center
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot from Rod n Reel Charter Fishing.
Pool
Spa
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive Annapolis MD
$101 nightly
The price is $115 total per night
$115 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
19.14 mi from city center
When you stay at SpringHill Suites by Marriott Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of Annapolis Harbour Center and Westfield Annapolis Mall.
Don't see what you're looking for?
See all available properties in Sherwood
View all properties
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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Sherwood hotels essential information

Accommodation
1,154 hotels
Lowest Price
$87
Highest Price
$203
Popular hotels
Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Crowne Plaza Annapolis by IHG, Hilton Garden Inn Annapolis Downtown, Graduate by Hilton Annapolis, Sonesta ES Suites Annapolis, Hyatt Regency Chesapeake Bay, The Westin Annapolis, Hampton Inn & Suites Annapolis, Rod 'N' Reel Resort, SpringHill Suites by Marriott Annapolis

Most Recent Sherwood Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"Brittnay was very helpful during our check-in. "
A verified traveler from SEVERNA PARK stayed at Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection