A large brick house with a green roof, surrounded by lush gardens and trees.

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Our top choices for Sherwood hotels

1. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (403 reviews)
"Enjoyed the fresh fruit and boiled eggs for breakfast!"
United States
Mary Ann
The price is NZ$237
includes taxes & fees
15 Nov - 16 Nov
Knapps Narrows Marina & Inn

2. Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (122 reviews)
"Very nice stay"
United States
Gary
The price is NZ$400
includes taxes & fees
2 Dec - 3 Dec
Wylder Tilghman Island

3. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,002 reviews)
"Convenient to St Michael’s and inexpensive."
United States
John
The price is NZ$156
includes taxes & fees
17 Nov - 18 Nov
St Michaels Inn

4. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (529 reviews)
"We’d definitely stay again. One areas for improvement-breakfast."
United States
Scott
The price is NZ$439
includes taxes & fees
1 Dec - 2 Dec
The Wildset

5. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (78 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
The price is NZ$354
includes taxes & fees
16 Nov - 17 Nov
George Brooks House B&B

6. Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (139 reviews)
"The staff were great. The breakfast was delicious and the location is perfect for walking into town."
United States
Susan
The price is NZ$494
includes taxes & fees
23 Nov - 24 Nov
Parsonage Inn

7. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is NZ$908
includes taxes & fees
7 Dec - 8 Dec
Inn at Perry Cabin

8. Baymont by Wyndham Easton

Baymont by Wyndham Easton
2.5 star property
Easton
6.6 out of 10, (31 reviews)
"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."
United States
Edwin
The price is NZ$159
includes taxes & fees
19 Nov - 20 Nov
Baymont by Wyndham Easton

9. Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (595 reviews)
"Pet friendly...very nice for our dog Staff helpful"
United States
Andrew
The price is NZ$253
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Easton

10. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,002 reviews)
"Place is gorgeous, clean and very welcoming."
United States
Patricia
The price is NZ$335
includes taxes & fees
30 Nov - 1 Dec
Rod 'N' Reel Resort

11. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
"Great place to stay"
United States
Michael
The price is NZ$268
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina

12. 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, (1,001 reviews)
"Staff was very friendly."
United States
Michelle
The price is NZ$190
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

13. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (397 reviews)
"Love this hotel, everyone was friendly and it was so clean! I’m really picky about where I stay and I would absolutely stay here again."
United States
Amanda
The price is NZ$250
includes taxes & fees
19 Nov - 20 Nov
Fairfield Inn & Suites by Marriott Easton

14. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.0 out of 10, Wonderful, (1,000 reviews)
"Plenty of parking! Comfortable beds and pillows. The staff was amazing, kind, helpful and friendly. I would definitely stay there again."
United States
Margaret
The price is NZ$235
includes taxes & fees
15 Nov - 16 Nov
Best Western Plus Easton Inn & Suites

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is NZ$164
includes taxes & fees
13 Dec - 14 Dec
Quality Inn Grasonville near Kent Island

16. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Nice location & stay"
United States
Holly
The price is NZ$179
includes taxes & fees
19 Nov - 20 Nov
Best Western Kent Narrows Inn

17. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,065 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is NZ$208
includes taxes & fees
23 Nov - 24 Nov
Historic Inns of Annapolis

18. The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (939 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
United States
Miriam
The price is NZ$336
includes taxes & fees
22 Nov - 23 Nov
The Tidewater Inn

19. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (523 reviews)
"Great place, very clean and fresh. Right next to a cool boathouse boat bar and overlooking the marina."
United States
David
The price is NZ$330
includes taxes & fees
30 Nov - 1 Dec
Anchored Inn at Hidden Harbour Marina

20. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is NZ$244
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
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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.

A large brick house with a green roof, surrounded by lush gardens and trees.

Top Sherwood Hotel Reviews

Recent Reviews in Sherwood

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

What is the best area to stay in Sherwood?
The best area to stay in Sherwood, Maryland, is along the waterfront of the Chesapeake Bay, particularly around Sherwood Road and its intersecting lanes.

This area is characterised by its direct access to the Chesapeake Bay, offering stunning water views and a tranquil setting. You'll find a mix of private holiday rentals and a few select guesthouses, many with their own jetties or private beach access. The general layout is quite spread out, with properties often set back from the main road, providing a sense of privacy.

For couples seeking a peaceful retreat, this waterfront stretch is ideal. You can enjoy quiet evenings watching the sunset over the Bay, perhaps indulging in fresh seafood from local purveyors, or simply relaxing by the water. It's a superb spot for unwinding and reconnecting away from the hustle and bustle.

Families will also find this area highly suitable. Many rentals offer spacious grounds, often with outdoor amenities like fire pits or space for lawn games. The proximity to the water means easy access for kayaking, paddleboarding, or just splashing around.
When is the best time to go to Sherwood?
The best time to go to Sherwood, Maryland, is during the shoulder seasons of late spring (May to early June) and early autumn (September to October).

These periods offer pleasant weather, with comfortable temperatures that are ideal for outdoor activities, without the intense heat and humidity of mid-summer. You'll also find fewer crowds compared to the peak summer months, allowing for a more relaxed experience at local attractions and eateries.

For those who enjoy water activities like sailing or kayaking, late spring and early autumn still provide ample opportunities to enjoy the Chesapeake Bay. The water is warm enough for swimming in early autumn, and the breezes are usually gentle, making for an enjoyable day out on the water.

If you're interested in local events and festivals, it's worth checking the Sherwood calendar.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Sherwood.
How can I save on a hotel booking in Sherwood with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Sherwood hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Sherwood?
Prices for hotels in Sherwood often vary, but you can find a great deal from NZ$151 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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