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. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,065 reviews)
"The room was very comfortable. This hotel is very close to the USNA."
United States
Joseph
2 days ago
$106 nightly
The price is $120
Dec 3 - Dec 4
Total with taxes and fees
Historic Inns of Annapolis

2. The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (172 reviews)
"The best vacation ever. Just a slice of heaven on earth."
United States
William
September 25th, 2026
The Tilghman Island Inn

3. 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
2 days ago
$120 nightly
The price is $132
Nov 15 - Nov 16
Total with taxes and fees
Knapps Narrows Marina & Inn

4. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,006 reviews)
"A truly wonderful fall getaway. Movies at the indoor pool."
United States
Amy
5 days ago
$194 nightly
The price is $221
Nov 15 - Nov 16
Total with taxes and fees
Hyatt Regency Chesapeake Bay

5. Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (122 reviews)
"The location was beautiful. The amenities were great. It was perfect."
United States
Angela
August 27th, 2026
$223 nightly
The price is $245
Dec 3 - Dec 4
Total with taxes and fees
Wylder Tilghman Island

6. 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
2 days ago
$90 nightly
The price is $99
Dec 13 - Dec 14
Total with taxes and fees
St Michaels 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)
"Property enhanced the dining experience. Outstanding experience in every way."
United States
Christina
September 29th, 2026
$459 nightly
The price is $505
Dec 7 - Dec 8
Total with taxes and fees
Inn at Perry Cabin

8. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,002 reviews)
"The property is very well maintained. Great views of Chesapeake Bay."
United States
Arthur
1 day ago
$167 nightly
The price is $185
Nov 30 - Dec 1
Total with taxes and fees
Rod 'N' Reel Resort

9. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,002 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
7 days ago
$215 nightly
The price is $245
Nov 23 - Nov 24
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,014 reviews)
"Bar staff were great. Front desk staff were great."
United States
Jennifer
3 days ago
$130 nightly
The price is $149
Nov 29 - Nov 30
Total with taxes and fees
Graduate by Hilton Annapolis

11. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (529 reviews)
"Wonderful place to stay. Everything is homemade."
United States
Dena
7 days ago
$222 nightly
The price is $244
Dec 1 - Dec 2
Total with taxes and fees
The Wildset

12. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,015 reviews)
"But the staff was helpful, the rooms were big and clean."
United States
Brian
2 days ago
$103 nightly
The price is $117
Dec 13 - Dec 14
Total with taxes and fees
Crowne Plaza Annapolis by IHG

13. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,012 reviews)
"Everything was very clean. The waitress in the restaurant was wonderful."
United States
Julie
2 days ago
$98 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Comfort Inn Conference Center

14. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,275 reviews)
"I visited with my young daughter. Everything about the facility made me feel safe."
United States
Rebecca
6 days ago
$89 nightly
The price is $102
Nov 22 - Nov 23
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis

15. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (860 reviews)
"I enjoyed my stay for two nights. My room was clean."
United States
Jean (Jeannie)
13 days ago
$134 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees
Hyatt Place Kent Narrows & Marina

16. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (46 reviews)
"Absolutely perfect little 3 day get away. Beautiful modern rooms."
United States
William
13 days ago
$489 nightly
The price is $538
Nov 15 - Nov 16
Total with taxes and fees
The Oaks Waterfront

17. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,010 reviews)
"I thoroughly enjoyed my stay! A great property and close to everything!"
United States
Leslie
16 days ago
$98 nightly
The price is $111
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown

18. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"Nice location to get to the Maryland REN Faire."
United States
joe
September 8th, 2026
$100 nightly
The price is $114
Nov 29 - Nov 30
Total with taxes and fees
Courtyard by Marriott Annapolis

19. Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.6 out of 10, Exceptional, (225 reviews)
"We stay at Sandaway every year for the St. Michael s Oyster Fest."
United States
Philip
2 days ago
$335 nightly
The price is $369
Nov 17 - Nov 18
Total with taxes and fees
Sandaway Suites & Beach

20. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,002 reviews)
"Shower pressure was very good. The room was very clean."
United States
Brittany
5 days ago
$84 nightly
The price is $96
Nov 24 - Nov 25
Total with taxes and fees
Sonesta ES Suites Annapolis
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Where to stay near Sherwood

Sherwood offers a delightful escape with its beautiful outdoor scenery and friendly atmosphere. Explore nearby areas for adventure and romance, all while enjoying family-friendly activities and relaxing days under sunny skies. It's the perfect destination for those seeking a charming and scenic getaway.

St. Michaels

Discover St. Michaels, a charming destination perfectly suited for families and couples seeking outdoor adventures and picturesque scenery. This delightful city offers a range of experiences, from the engaging exhibits at the Chesapeake Bay Maritime Museum to the iconic 1879 Hooper Strait Lighthouse and scenic strolls along the St. Michaels Marina. Located about 12 miles by car from Sherwood, St. Michaels makes for a smart hotel booking choice, ensuring a memorable getaway amidst nature's beauty.

Bozman

Experience the charm of Bozman, an excellent hub for travelers seeking a weekend getaway with family or a nature-focused retreat. Just about 6 miles by car from Sherwood, Bozman offers easy access to scenic spots like the Chesapeake Bay Maritime Museum and the historic 1879 Hooper Straight Lighthouse, alongside opportunities for outdoor recreation at St. Michaels Marina. With its blend of beach and lake experiences, Bozman is a smart choice for your next vacation stay.

Wittman

If you are a nature enthusiast or a family traveler, look no further than Wittman, a charming city known for its scenic beauty and outdoor adventures. Visitors can explore the Chesapeake Bay Maritime Museum, marvel at the historic 1879 Hooper Straight Lighthouse, or relax at St. Michaels Marina. Wittman is about a 3-mile drive from Sherwood, making it easy to access the area's stunning bay and beach. Choosing Wittman for your stay ensures a delightful blend of relaxation and exploration.

Tilghman

Ideally situated for families, nature lovers, and couples seeking a romantic getaway, Tilghman is a charming destination that invites visitors to immerse themselves in its stunning scenery. Just a short drive from Sherwood, Tilghman offers easy access to outdoor recreational areas, a beautiful bay, and a welcoming beach. Explore local highlights like the Tilghman Island Marina, the Tilghman Watermen’s Museum, and the Phillips Wharf Environmental Center. Choosing Tilghman for your stay ensures a memorable experience in a picturesque setting.

Neavitt

Travelers seeking a weekend getaway will find Neavitt to be the ideal base for their vacation, featuring stunning outdoor experiences and family-friendly activities. With attractions like the Chesapeake Bay Maritime Museum, the Tilghman Island Marina, and the picturesque 1879 Hooper Straight Lighthouse, visitors can immerse themselves in the natural beauty and rich maritime heritage of the area. Located about 17 miles by car from Sherwood, Neavitt offers a delightful escape that makes it a smart choice for your stay.

Stay near popular attractions in and around Sherwood

Experience the perfect blend of outdoor adventures and cultural richness in Sherwood. With stunning parks, a picturesque marina, and engaging museums, you'll find endless activities that cater to families and nature lovers alike. Discover the beauty and charm that makes Sherwood an unforgettable getaway.

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

More cheap stays in Sherwood

Hotels in Sherwood with star-rating

Find out more about Sherwood

Top reasons to visit Sherwood

  • Scenic Outdoor Activities: Sherwood offers beautiful outdoor spaces, perfect for relaxation and exploration, including a private beach and access to the Chesapeake Bay.
  • Vibrant Local Scene: Enjoy live music events that contribute to the lively atmosphere of the community.
  • Rich Cultural Experiences: Visit nearby history museums and urban parks for a taste of local culture.
  • Family-Friendly Vibe: Sherwood is ideal for families seeking a peaceful and enjoyable getaway.
  • Comfortable Accommodations: Choose from charming bed & breakfasts to modern hotels, catering to all needs.

Find great hotels near Sherwood

Discover a range of comfortable accommodations in Sherwood, Maryland, perfect for your vacation. Whether you're seeking a cozy bed & breakfast or a modern hotel, you'll find options that cater to your needs. Enjoy pet-friendly facilities and amenities like free Wi-Fi at popular spots such as the Lowes Wharf Marina Inn and Residence Inn. Experience the adventure and beach vibes that make Sherwood a great destination for travelers.

  • St Michaels Inn: St Michaels Inn is a budget-friendly hotel with a guest rating of 8.2 out of 10, located 6 miles from Sherwood. This property caters to adventurers and business travelers alike, providing a range of outdoor activities nearby. Guests can enjoy bicycle rentals, hiking, hunting, and fishing in the surrounding areas. The Inn offers a cozy atmosphere perfect for those seeking an affordable yet adventurous stay, making it a great choice for those looking to explore the natural beauty of the region.
  • Rod 'N' Reel Resort: With a guest rating of 8.4 out of 10, Rod 'N' Reel Resort is a 3-star establishment situated 13 miles from Sherwood. Ideal for families and adventure seekers, this resort features a variety of onsite activities, including boat tours, fishing, and personal motor watercraft rentals. For families, amenities such as a ping pong table, arcade game room, and special breakfast options for children enhance the experience. The resort’s blend of fun and relaxation makes it a perfect destination for both leisure and business travelers.
  • The Tidewater Inn: Rated 8.8 out of 10, The Tidewater Inn is a charming 3-star hotel located 13 miles from Sherwood. This property offers a unique combination of adventure and relaxation with activities like kayaking, sailing, and hiking nearby. For those seeking rejuvenation, the full-service spa provides couples' treatment rooms, massages, and body scrubs. The Tidewater Inn is an excellent choice for travelers looking to unwind in a serene environment while enjoying a variety of recreational options.

Where to stay near Sherwood

Explore the charming town of Sherwood, Maryland, where outdoor adventures and scenic views await. Enjoy the tranquil atmosphere at the private beach and wharf, or take a trip to the nearby Chesapeake Bay for a delightful island experience. With its friendly locals and family-friendly vibe, Sherwood is the perfect destination for those seeking relaxation and historical charm. Discover the beauty of this sunny region during your vacation.

  • St. Michaels: Nestled approximately 5 miles from Sherwood, St. Michaels is a charming coastal town renowned for its picturesque scenery and outdoor activities. The town experiences a moderate influx of visitors, particularly during April and the summer months of June and July. Travelers flock here to enjoy the beautiful beaches, scenic views, and vibrant boardwalks. St. Michaels boasts a variety of recreational areas where you can relax and soak up the sun, making it ideal for both family outings and romantic getaways. Local attractions include the family-friendly beach and the stunning bay, which are perfect for water sports or leisurely strolls.
  • Bozman: Located just 3 miles from Sherwood, Bozman is a hidden gem that offers a unique blend of outdoor adventures and scenic beauty. This city sees a steady stream of visitors throughout the year, peaking in March and the summer months of June to July. Here, you can explore the inviting recreational areas and enjoy a day of shopping at local centers. The nearby bay and lake provide ample opportunities for fishing, kayaking, or simply enjoying a day by the water. Bozman's welcoming atmosphere and natural beauty make it a perfect spot for those seeking a quieter, more laid-back experience.
  • Wittman: Also situated 3 miles from Sherwood, Wittman is an inviting town that attracts visitors year-round, especially in the summer months from June to August. Known for its stunning outdoor spaces and serene scenery, Wittman is perfect for nature enthusiasts. The area offers various recreational opportunities, including boardwalks and parks, where you can immerse yourself in the area's natural beauty. Nearby attractions include the beautiful bay, beach, and national state park, making Wittman a great base for exploring the great outdoors while enjoying the local charm.

Things to do near Sherwood

In Sherwood, Maryland, visitors can enjoy a delightful blend of outdoor activities and scenic beauty. The area features a recreational space perfect for relaxation, a charming boardwalk, and educational opportunities. Don't miss out on the vibrant local scene, highlighted by live music events that add to the community's lively atmosphere. Whether you're looking for a beach getaway or just a peaceful retreat, Sherwood has something for everyone.

Shopping

In Sherwood, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, head to nearby shopping malls like the Montgomery Mall or the Westfield Wheaton for a wider selection of stores and dining options to enhance your shopping experience.

Recreation

At Old South Country Club, just 19 miles from Sherwood, immerse yourself in luxury with top-notch wellness amenities. Enjoy serene golf courses, rejuvenating spa treatments, and upscale dining options, all set against a picturesque backdrop, perfect for relaxation and rejuvenation.

Adventure

In Sherwood, explore the scenic trails of Patuxent River Park for hiking and biking adventures. Experience thrilling water activities on the Patuxent River, including kayaking and canoeing, perfect for nature lovers seeking excitement and relaxation amidst stunning views.

Nightlife

Explore the vibrant nightlife at the Sherwood Lounge, where you can enjoy signature cocktails and a lively atmosphere. For dancing, check out the nearby Club 47, featuring local DJs and themed nights that keep the energy high and the party going.

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

Booking tips and Expedia advantages for Sherwood

  • 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: Utilize Expedia’s search tool to narrow down your options based on your preferences, such as budget, desired location, and hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Sherwood with your flights and activities through an Expedia package deal.

Find the best attractions near Sherwood

Sherwood, Maryland, is perfect for outdoor enthusiasts and families seeking a scenic beach vacation. You can explore a variety of attractions, including marinas, urban parks, and history museums, which offer rich cultural experiences. Whether you're looking to enjoy nature or delve into local history, Sherwood has something for everyone, ensuring a memorable getaway.

  • Chesapeake Bay Maritime Museum: Located 6 miles from Sherwood, this maritime museum offers a deep dive into the rich cultural heritage of the Chesapeake Bay. Explore exhibits showcasing traditional boat building, local wildlife, and the maritime history of the region.
  • Rod n Reel Charter Fishing: A short 13 miles away, this marina is perfect for those seeking adventure on the water. Enjoy charter fishing trips that provide thrilling experiences against the beautiful backdrop of the bay, along with opportunities for outdoor fun on the beach.
  • Tilghman Watermen’s Museum: Just 4 miles from Sherwood, this history museum highlights the lives and traditions of local watermen. Engage with exhibits that celebrate the unique culture and history of the fishing community in the area.

Best time to go to Sherwood

The best time to visit Sherwood is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

When planning your trip to Sherwood, Maryland, you'll find convenient access to three major airports. Ronald Reagan Washington National Airport (DCA) is 39 miles away, with excellent nearby hotels like the 5-star InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 2 miles from the airport. Washington Dulles International Airport (IAD) is 62 miles distant, featuring hotels such as the 4-star Westin Washington Dulles Airport and Hyatt Regency Dulles International Airport, both 1 mile away. Lastly, Baltimore Washington International Airport (BWI) is 34 miles from Sherwood, offering luxurious options like Pendry Baltimore and Four Seasons Hotel Baltimore, approximately 8 miles 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, particularly around the Sherwood Road and Claiborne Road intersection, where many of the town's key amenities are located.

This central area offers direct access to the Chesapeake Bay, providing scenic water views and opportunities for activities like kayaking or paddleboarding. It's the hub for local dining and community gatherings, making it convenient for visitors to experience the local character.

Couples often find this area appealing due to the serene waterfront setting and the availability of accommodations with Bay views. The proximity to local eateries and the public pier creates a relaxing environment for romantic strolls and enjoying sunsets over the water.

For travelers seeking a quiet retreat with easy access to nature, the areas slightly inland from the main waterfront, particularly near the fishing and crabbing spots, offer a peaceful escape.
When is the best time to go to Sherwood?
The best time to visit Sherwood, Maryland, is during the shoulder seasons of late spring (April-May) and early fall (September-October).

During these months, you'll experience pleasant temperatures, fewer crowds, and a full range of outdoor activities. The weather is typically sunny and mild, superb for exploring the Chesapeake Bay, enjoying watersports, or hiking the local trails without the intense heat and humidity of summer. Many local establishments, from eateries to attractions, are fully operational, offering a complete experience for visitors.

For those looking for a quiet, relaxing getaway, these times of year are ideal. You can enjoy the natural beauty of the area, like the scenic views along the Chesapeake Bay, and take advantage of outdoor activities like kayaking or biking without the peak season influx of people.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 much is the nightly rate at a Sherwood hotel?
Prices for hotels in Sherwood often vary, but you can find a great deal from $84 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 the cheapest rate.

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