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28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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Our top choices for Sherwood hotels

1. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
United States
BARBARA
NZ$291
includes taxes & fees
29 Sept - 30 Sept
Knapps Narrows Marina & Inn

2. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
NZ$359
includes taxes & fees
29 Sept - 30 Sept
The Tilghman Island Inn

3. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
United States
Gary
NZ$412
includes taxes & fees
30 Sept - 1 Oct
Wylder Tilghman Island

4. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
NZ$173
includes taxes & fees
4 Oct - 5 Oct
St Michaels Inn

5. The Wildset

The Wildset
Downtown St. Michaels
United States
Sarah
NZ$508
includes taxes & fees
5 Oct - 6 Oct
The Wildset

6. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Raheem
NZ$251
includes taxes & fees
29 Sept - 30 Sept
Best Western Plus Easton Inn & Suites

7. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
United States
Ellen
NZ$192
includes taxes & fees
29 Sept - 30 Sept
Baymont by Wyndham Easton

8. George Brooks House B&B

George Brooks House B&B
St. Michaels
United States
Erin
NZ$411
includes taxes & fees
29 Sept - 30 Sept
George Brooks House B&B

9. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
NZ$996
includes taxes & fees
26 Oct - 27 Oct
Inn at Perry Cabin

10. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Dale
NZ$382
includes taxes & fees
20 Oct - 21 Oct
Anchored Inn at Hidden Harbour Marina

11. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
NZ$261
includes taxes & fees
25 Oct - 26 Oct
Rod 'N' Reel Resort

12. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
NZ$216
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG

13. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Amber
NZ$583
includes taxes & fees
8 Oct - 9 Oct
Sandaway Suites & Beach

14. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Crystal
NZ$196
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Grasonville near Kent Island

15. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
NZ$195
includes taxes & fees
30 Sept - 1 Oct
DoubleTree by Hilton Hotel Annapolis

16. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
NZ$317
includes taxes & fees
14 Oct - 15 Oct
The Tidewater Inn

17. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
United States
Amanda
NZ$263
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Easton

18. Hampton Inn Easton

Hampton Inn Easton
Easton
United Kingdom
Rachel
NZ$290
includes taxes & fees
27 Oct - 28 Oct
Hampton Inn Easton

19. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
NZ$298
includes taxes & fees
6 Oct - 7 Oct
Hyatt Place Kent Narrows & Marina

20. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
NZ$855
includes taxes & fees
30 Sept - 1 Oct
The Oaks Waterfront
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Stay near popular Sherwood attractions

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
See properties

Back Creek Community Park

Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.
See properties

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.

See all hotels in Sherwood
A large brick house with a green roof, surrounded by lush gardens and trees.

Top Sherwood Hotel Reviews

Recent Reviews in Sherwood

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Conveniently located property, nicely maintained. Improvements could be better selections for the breakfast buffet, especially since it’s not complimentary."
Maria 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."
kelly 2-night trip
Posted 17 hours ago
Sonesta ES Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"."
Rebecca 3-night trip
Posted 21 hours ago
Holiday Inn Express & Suites Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Beautiful location. Indoor pool is fabulous."
Carolyn 5-night trip
Posted 1 day ago
Hyatt Regency Chesapeake Bay
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"
Rathna 1-night trip
Posted 3 days ago
The Inn at Chesapeake Bay Beach Club
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."
William 1-night trip
Posted 7 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 7 days ago
The Westin Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"I thought breakfast was included but apparently not . There was not even complimentary coffee"
Gerald 2-night trip
Posted 7 days ago
Courtyard by Marriott Annapolis

More cheap accommodation in Sherwood

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
NZ$158
4 Oct - 5 Oct
includes taxes & fees
7.8/10 Good! (1,003 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
NZ$173
4 Oct - 5 Oct
includes taxes & fees
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
NZ$207
26 Oct - 27 Oct
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
NZ$213
5 Oct - 6 Oct
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
Hampton Inn & Suites Annapolis
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
NZ$249
5 Oct - 6 Oct
includes taxes & fees
Best Western Kent Narrows Inn
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD
NZ$251
29 Sept - 30 Sept
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
Best Western Plus Easton Inn & Suites

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 program—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$158 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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