Sherwood Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Sherwood

Lowes Wharf Marina Inn
Lowes Wharf Marina Inn
3 out of 5
21651 Lowes Wharf Rd, Sherwood, MD
7.6/10 Good! (71 reviews)
"Very relaxing ( we were there midweek). Incredible location and sunsets."

Reviewed on 23 Sep,2024

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Lowes Wharf Marina Inn
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$214 per night from 23 Dec to 24 Dec
S$214
includes taxes & fees
23 Dec - 24 Dec
8.8/10 Excellent! (1,693 reviews)
"My husband and I stayed at the Governor Calvert House for 3 nights. We were able to book an extra night and were even able to check in earlier, with no fee, if we wanted! The staff was friendly, the Inn was ADORABLE, and we loved how accessible it was to everything. Truly felt like a Hallmark movie ..."

Reviewed on 27 Nov,2024

Historic Inns of Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$200 per night from 24 Dec to 25 Dec
S$200
includes taxes & fees
24 Dec - 25 Dec
9.2/10 Wonderful! (986 reviews)
"Very smooth checkin. The property is in a great location and is very clean."

Reviewed on 3 Nov,2024

Graduate by Hilton Annapolis
See all 1,122 properties in Sherwood
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.

Frequently asked questions

How much does a Sherwood holiday package cost?
From as little as . Yes, you read that right. Our Sherwood packages are the easiest way to make your budget last longer. Bundle your preferred hotels, flights and car rentals and get out and see this lively destination.
How do I get a cheap travel package to Sherwood?
If you love landing a bargain, bundle your bookings into a Sherwood holiday package. Whether you’re searching for flights, hotels, activities or rental cars, you can browse and book them all in one place. You’ll have loads of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 properties across the globe to pick from. Fly with who you want, stay in a place you like and save a tidy sum — now that’s the ideal getaway!
What are the top hotels in Sherwood?
Waterfront - Private 153 Acre Historic Estate and Lowes Wharf Marina Inn are among the most popular properties in Sherwood. Why not look up the rates and facilities at each and then make a decision?
How far in advance should I book my Sherwood holiday?
Travellers are generally able to compare international airfares on Expedia within 12 months of departure. Booking at the last minute? With a stroke of luck, it’s still possible to nab an affordable ticket just weeks before your journey.
What does an Expedia Sherwood travel package include?
Hotels, flights and a shiny set of wheels for your road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you’ve made your booking, add on a few tours and activities and watch your savings pile up. When it comes to planning your Sherwood trip, you’re in control!
What should I know before booking a Sherwood travel package?
Booking all the parts of your getaway together is a terrific way to save. Combine your flights, car rentals and hotels into a neat little package. But you’re not restricted to hotels. Expedia offers all kinds of properties, including holiday rentals like beach villas and city apartments. Your choices are almost endless!
Can I choose my airline with a Sherwood Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Sherwood holiday package?
Certainly, and we’ll help you every step of the way. You may be able to cancel or amend your Sherwood holiday package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If your circumstances suddenly change, take a look at our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.