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Our top choices for Sherwood hotels

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (684)
"friendly staff, clean room / lobby, nice bar, everything was great"
United States
William
The price is NZ$222
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is NZ$282
includes taxes & fees
13 Jan - 14 Jan 2026
Parsonage Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NZ$161
includes taxes & fees
2 Jan - 3 Jan 2026
Quality Inn Grasonville near Kent Island

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
George Brooks House B&B

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (372)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is NZ$1,229
includes taxes & fees
2 Jan - 3 Jan 2026
Inn at Perry Cabin

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, (945)
"It was very comfortable and clean"
United States
Maria
The price is NZ$182
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1000)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is NZ$181
includes taxes & fees
4 Jan - 5 Jan 2026
St Michaels Inn

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Clean and friendly staff"
United States
Lisa
The price is NZ$234
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Kent Island Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is NZ$388
includes taxes & fees
18 Jan - 19 Jan 2026
The Tilghman Island Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1000)
"Nice place "
United States
Tucker T
The price is NZ$159
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Kent Narrows Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is NZ$287
includes taxes & fees
4 Jan - 5 Jan 2026
Kent Island Resort

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is NZ$299
includes taxes & fees
6 Jan - 7 Jan 2026
Wylder Tilghman Island

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is NZ$359
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Chesapeake Bay Beach Club

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (412)
"Everything was lovely. "
United States
Erin
The price is NZ$377
includes taxes & fees
1 Jan - 2 Jan 2026
The Wildset

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (472)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is NZ$262
includes taxes & fees
29 Jan - 30 Jan 2026
Anchored Inn at Hidden Harbour Marina

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1002)
"Very courteous staff."
United States
Joseph
The price is NZ$384
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Regency Chesapeake Bay

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
Easton
9.6 out of 10, Exceptional, (368)
"Great hotel, very clean & quiet. "
United States
Janet
The price is NZ$345
includes taxes & fees
11 Jan - 12 Jan 2026
Fairfield Inn & Suites by Marriott Easton

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
The price is NZ$782
includes taxes & fees
31 Dec - 1 Jan 2026
The Oaks Waterfront

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick
2.5 star property
Prince Frederick
7.6 out of 10, Good, (213)
"Good place to stay in the area"
United States
Eduardo
The price is NZ$140
includes taxes & fees
8 Jan - 9 Jan 2026
SureStay by Best Western Prince Frederick
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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Stay near popular Sherwood attractions

Learn more about Sherwood

Explore the historic Sherwood Forest community with its charming waterfront homes and private marina along the Severn River. Nearby Annapolis offers sailing excursions, while local residents enjoy exclusive access to the community beach and tennis courts.

Gardens and large home at Sherwood Gardens Park, in Baltimore, M

Top Sherwood Hotel Reviews

More cheap accommodation in Sherwood

Find out more about Sherwood

Top reasons to visit Sherwood

  • Outdoor Adventures: Sherwood offers scenic walks, recreational areas, and excellent golf courses for adventure enthusiasts.
  • Romantic Getaways: The picturesque setting makes it ideal for couples seeking a charming escape.
  • Cultural Experiences: Discover local attractions like history museums and urban parks for a taste of the region's heritage.
  • Beautiful Gardens: Explore the nearby Queenstown Gardens, perfect for relaxation and enjoying nature.
  • Comfortable Accommodations: Choose from quaint bed & breakfasts to pet-friendly hotels for a welcoming stay.

Find great hotels near Sherwood

Explore a variety of comfortable accommodation options in Sherwood, Maryland, perfect for your vacation. Choose from quaint bed & breakfasts or welcoming hotels that cater to pet-friendly needs and adventurous beach getaways. Whether you’re seeking a relaxing retreat or a friendly atmosphere, Sherwood has the ideal lodging to enhance your travel experience.

  • St Michaels Inn: Nestled 9.7km from Sherwood, St Michaels Inn is the perfect retreat for adventurous souls and business travellers alike. This hotel caters to those seeking a blend of adventure and professional amenities. The property boasts several business facilities, including a well-equipped meeting room, conference centre, and conference space. For the adventurous, there are numerous recreation opportunities nearby such as bicycle rentals, fishing, hiking, and hunting. Guests appreciate the convenience of being close to nature while having access to essential business services, making it an ideal choice for a dynamic vacation experience.
  • Rod 'N' Reel Resort: Located 20.9km from Sherwood, the Rod 'N' Reel Resort is a 3-star haven for those who love nature and adventure while needing business amenities. This vibrant resort features multiple meeting rooms and conference spaces, ensuring that business needs are met without sacrificing leisure. Guests can indulge in onsite boat tours and fishing, or explore hiking and biking trails in the vicinity. With facilities like a fish cleaning table and personal motor watercraft available, this resort is a popular choice for those seeking both relaxation and adventure in a beautiful natural setting.
  • The Tidewater Inn: A charming 3-star establishment situated 20.9km from Sherwood, The Tidewater Inn is perfect for those seeking a unique blend of business, adventure, and spa experiences. With multiple meeting rooms and a comprehensive business centre, it caters to professional needs while offering a full-service spa for ultimate relaxation. Adventure seekers can enjoy activities such as kayaking, sailing, and boat tours nearby. Guests rave about the spa's treatment rooms and massage services, making it a top choice for a rejuvenating getaway that combines work and leisure seamlessly.

Where to stay near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor adventures and romantic getaways, perfect for any traveller. With its stunning scenery and friendly locals, visitors can explore nearby towns and enjoy a family-friendly atmosphere. Experience the historical charm and relaxing vibe of the region, all under sunny skies. Whether you're wandering through charming neighbourhoods or soaking in the local culture, Sherwood promises an unforgettable holiday experience reminiscent of the breathtaking landscapes of Queenstown, New Zealand.

  • St. Michaels: Nestled about 8.0km from Sherwood, St. Michaels is a charming town known for its picturesque waterfront and vibrant outdoor activities. This quaint city experiences moderately seasonal traveller numbers, peaking in April and from June to July, making it a bustling spot during those months. Visitors flock to St. Michaels for romantic getaways and family-friendly adventures, enjoying its scenic boardwalk and recreational areas. Key attractions include lovely beaches and serene lakes, perfect for a day of sun and fun. The welcoming atmosphere and local eateries add to the charm, ensuring a delightful experience.
  • Tilghman: Located a mere 6.4km from Sherwood, Tilghman offers a unique blend of scenic beauty and outdoor enjoyment. This small city sees its visitor numbers peak during the summer months, particularly from June to August, attracting those who appreciate nature and tranquillity. Known for its stunning views and romantic settings, Tilghman provides ample opportunities for outdoor activities along its beautiful beaches and lakes. With a relaxed vibe and local events, it’s an excellent spot for travellers seeking picturesque landscapes and memorable experiences.
  • Bozman: Just 4.8km from Sherwood, Bozman is a hidden gem that captivates visitors year-round with minimal seasonal fluctuations in traveller arrivals. The town sees a spike in visitors during March and from June to July, drawing those interested in outdoor pursuits and scenic experiences. Bozman offers easy access to beautiful beaches and recreational areas, making it ideal for a relaxing escape. With its charming atmosphere and natural beauty, Bozman is perfect for those looking to connect with nature while enjoying a peaceful getaway.

Things to do near Sherwood

Sherwood, Maryland, is perfect for outdoor and romantic getaways, offering a blend of culture and nature. Visitors can explore scenic walks, enjoy the recreational area, and take in the sights along the boardwalk. For those interested in golf, there are excellent courses available. Whether you're keen on sightseeing or simply relaxing in a picturesque setting, Sherwood provides a charming escape.

Shopping

For a delightful shopping experience in Sherwood, visit Saint Michaels Village, a vibrant shopping centre just 9.7km away. If you're up for a drive, Easton Cycle and Sport, located 22.5km away, offers a unique selection, and the Bay Bridge Market Place Shopping Center, 19.7km away, features entertainment and family-friendly vibes.

Recreation

At Hog Neck Golf Course, enjoy a round of golf surrounded by beautiful landscapes, perfect for outdoor enthusiasts. Talbot Massage offers soothing body treatments that promote wellness and relaxation, while the Ballet Theater of Maryland provides a cultural experience filled with dance, romance, and entertainment.

Adventure

Chesapeake Beach Water Park offers thrilling water slides and family-friendly entertainment, perfect for a fun-filled day 20.9km from Sherwood. Explore the scenic St Michaels Nature Trail, a 8.0km journey ideal for outdoor enthusiasts seeking adventure. For water sports, join Annapolis Sailing School, located 25.7km away, for exhilarating sailing experiences.

Nightlife

A night in Sherwood offers a trip to the Avalon Theatre for a dose of culture and romance, or venture to Annapolis Bowl for some thrilling arcade fun. For a cinematic experience, Regal Waugh Chapel provides the perfect blend of entertainment and romance, making it a memorable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sherwood

For a budget-friendly trip to Sherwood, consider visiting between January and March when accommodation prices are lower, especially on Tuesdays. Avoid Saturdays to save on costs. Use Expedia’s search tool to find the best deals by sorting prices and selecting Eco-certified hotels for sustainable options. Combine your hotel, flights, and activities for additional savings through package deals. Look out for free activities in the area to further stretch your budget while enjoying the local culture.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sherwood are January to March, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sherwood is Tuesday. The most expensive day to stay in Sherwood is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool lets you tailor your travel plans by choosing your budget, desired location, and other preferences. You can easily organise your search results to display prices from lowest to highest, ensuring you find the most affordable accommodation first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will show you a range of sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: Consider saving some cash by combining your Sherwood hotel booking with your flights and activities through an Expedia package deal.

Find the best attractions near Sherwood

Sherwood, Maryland, offers a delightful mix of outdoor adventures, romantic spots, and cultural experiences for all types of travellers. Visit local attractions such as the history museum, marina, and urban park, perfect for family outings or a leisurely stroll. Don’t miss exploring the beautiful Queenstown Gardens nearby, adding a touch of nature to your holiday. Sherwood is sure to provide a memorable experience for every visitor.

  • Chesapeake Bay Maritime Museum: Located 9.7km from Sherwood, this maritime museum offers a deep dive into the rich maritime heritage of the region. Explore exhibits showcasing the traditional boat-building techniques and the cultural significance of the Chesapeake Bay.
  • Tilghman Watermen’s Museum: Situated 6.4km from Sherwood, this history museum celebrates the lives of local watermen. Experience the unique culture and traditions of the area's fishing community through fascinating displays and stories.
  • Tilghman Island Marina: Just 4.8km from Sherwood, this marina is the perfect spot for outdoor adventures. Enjoy activities such as boating, fishing, and beach relaxation while soaking up the picturesque views of the bay.

Best time to go to Sherwood

The best time to visit Sherwood can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sherwood falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Sherwood falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February38.8°F (3.8°C)Light RainMostly SunnyLowSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyHighSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyHighAverage
May64.6°F (18.1°C)Light RainMostly SunnyHighAverage
June73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyAverageAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
October61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly High
November49.5°F (9.7°C)Light RainMostly SunnyAverageAverage
December42.3°F (5.7°C)Light RainMostly SunnyAverageAverage

The nearest major airports for your trip to Sherwood

For your visit to Sherwood, Maryland, you can fly into three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 62.8km away, with nearby 5-star options like the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 3.2km from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 54.7km away, featuring luxurious hotels such as Sagamore Pendry Baltimore, which offers an airport shuttle service. Lastly, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) is 53.2km distant, with more budget-friendly choices like Country Inn & Suites by Radisson, just 3.2km from the airport.

Frequently asked questions

Where is the best place to stay in Sherwood?
DoubleTree by Hilton Hotel Annapolis, located 19.5 mi (31.4 km) from the heart of Sherwood, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Sherwood.
What are some of the best holiday rentals that Sherwood has to offer?
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This holiday home rental outside of Sherwood is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Sherwood.
If I need to cancel my hotel reservation in Sherwood, will I receive a refund?
Yes, most hotel reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sherwood.
What's the best dog-friendly place to stay in Sherwood?
Lowes Wharf Marina Inn is a top inn for people travelling with their pets, and offers a marina and a restaurant for its human guests. See more pet-friendly hotel accommodations in Sherwood.
What are some hotels with pools in Sherwood?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Hyatt Regency Chesapeake Bay and Hampton Inn & Suites Annapolis are a couple of other choices with an on-site pool. View all hotels with pools in Sherwood.
What's it like to stay in Sherwood?
Visitors can enjoy all that Sherwood has to offer, including the waterfront and restaurants. This city also attracts tourists with its scenic and welcoming setting. In Sherwood, there are 8 hotels and other accommodation options to choose from. Find out more about Sherwood.
What are the top places to visit in Sherwood?
A couple of favourite places to visit are Knapp's Narrows Marina & Inn and Goat Island. You'll also find St. Michaels Winery and St. Michaels Marina in the area. Take a look at what more there is to see and do in Expedia's Sherwood guide.
What's the seasonal weather like in Sherwood?
The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Sherwood is 1341 mm.

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