Sherwood Hotels

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Our top choices for Sherwood hotels

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
Wake up to a full complimentary breakfast at this cozy B&B in St. Michaels before exploring Perry Cabin Park and nearby marinas. Enjoy free WiFi and parking while unwinding in the peaceful garden and terrace after hiking local trails.

"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is P8,770
P9,647 total
includes taxes & fees
Jan 7 - Jan 8
Parsonage Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (691)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Center and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.

"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is P6,830
P7,581 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina

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 P10,007
P11,007 total
includes taxes & fees
Jan 7 - Jan 8
George Brooks House B&B

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links for easy exploration.

"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is P4,953
P5,498 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Grasonville near Kent Island

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, (946)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available onsite. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Center after a quiet night's rest.

"It was very comfortable and clean"
United States
Maria
The price is P5,122
P5,686 total
includes taxes & fees
Jan 19 - Jan 20
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, (1001)
Experience serene stays at this peaceful inn with seasonal outdoor pool and garden terrace. Located conveniently near Saint Michaels Village and Classic Motor Museum, guests appreciate the helpful staff, clean rooms, and complimentary breakfast, WiFi, and parking.

"Good value and close to downtown."
United States
John
The price is P5,920
P6,512 total
includes taxes & fees
Jan 12 - Jan 13
St Michaels Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (372)
Set on the waterfront, this charming inn offers a relaxing retreat with a full-service spa and outdoor pool. Play golf, dine at Stars restaurant, or enjoy drinks at 2 bars. Close to Perry Cabin Park with helpful staff to enhance your stay.

"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is P33,551
P40,597 total
includes taxes & fees
Jan 15 - Jan 16
Inn at Perry Cabin

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Center.

"Nice place "
United States
Tucker T
The price is P4,910
P5,450 total
includes taxes & fees
Feb 1 - Feb 2
Best Western Kent Narrows 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)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness center for active travelers. Explore nearby Chesapeake Bay Environmental Center, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.

"Clean and friendly staff"
United States
Lisa
The price is P7,192
P7,983 total
includes taxes & fees
Jan 11 - Jan 12
Hilton Garden Inn Kent Island Marina

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)
Located in Stevensville with easy access to Paul Reed Smith Guitars and Northern Chesapeake Bay, this hotel offers spa treatments, an outdoor pool, and a café. Enjoy free WiFi and parking while the helpful staff ensures a memorable stay.

"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 P9,180
P11,687 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Chesapeake Bay Beach Club

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 P7,076
P9,904 total
includes taxes & fees
Jan 4 - Jan 5
Kent Island Resort

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
This charming Tilghman inn offers stunning water views with convenient access to Tilghman Island Marina. Enjoy a complimentary breakfast before lounging by the seasonal outdoor pool or exploring the garden. The friendly staff and relaxing bar enhance your Eastern Shore getaway.

"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is P11,772
P12,950 total
includes taxes & fees
Feb 1 - Feb 2
The Tilghman Island Inn

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
This elegant B&B features a seasonal outdoor pool and relaxing hot tub for unwinding after exploring nearby attractions. Free bike rentals invite local adventure while complimentary breakfast, WiFi, and parking enhance the luxury experience.

"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 P6,936
P10,220 total
includes taxes & fees
Jan 18 - Jan 19
Wylder Tilghman Island

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (473)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is P7,893
P8,999 total
includes taxes & fees
Jan 11 - Jan 12
Anchored Inn at Hidden Harbour Marina

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (412)
Located in St. Michaels, this welcoming hotel offers free breakfast, WiFi, and parking. Enjoy drinks at the bar or grab a bite at the café. Nearby attractions include Higgins Yacht Yard and Muskrat Park, with attentive staff to enhance your stay.

"Everything was lovely. "
United States
Erin
The price is P10,536
P12,885 total
includes taxes & fees
Jan 7 - Jan 8
The Wildset

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)
Tucked in Prince Frederick, this hotel offers free WiFi, parking, and daily continental breakfast. Explore nearby Calvert Historical Society Park and King Memorial Park, or take a day trip to Ronald Reagan Washington National Airport just over an hour away.

"Good place to stay in the area"
United States
Eduardo
The price is P4,325
P4,800 total
includes taxes & fees
Jan 8 - Jan 9
SureStay by Best Western Prince Frederick

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (363)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.

"nice clean room staff very nice would stay again "
United States
mario
The price is P5,888
P6,476 total
includes taxes & fees
Jan 4 - Jan 5
Knapps Narrows Marina & Inn

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
2.5 star property
Prince Frederick
8.8 out of 10, Excellent, (699)
This modern hotel offers an indoor pool and fitness center just minutes from calvART Gallery and R&J's PlayPark. Enjoy complimentary breakfast, WiFi, and parking while the attentive staff ensures a pleasant stay.

"Great environment, friendly staff, great place to stay with family and lots of things to do around the area!"
United States
Rosemary
The price is P6,064
P7,385 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express Prince Frederick by IHG

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
Easton
9.6 out of 10, Exceptional, (368)
Start your day with complimentary breakfast at this Easton retreat, then swim in the indoor pool or exercise in the fitness center. The friendly staff, free parking, and in-room refrigerators create a convenient base near Talbot Massage.

"Great hotel, very clean & quiet. "
United States
Janet
The price is P9,458
P10,404 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott Easton
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 stays in Sherwood

Find out more about Sherwood

Top reasons to visit Sherwood

  • Scenic Outdoor Adventures: Experience the natural beauty of the Eastern Shore with various outdoor activities and stunning river views.
  • Charming Local Hangouts: Enjoy vibrant shopping centres and friendly local spots perfect for relaxation and socialising.
  • Cultural Attractions: Explore history museums and urban parks that offer enriching experiences for families and culture enthusiasts.
  • Romantic Atmosphere: Witness breathtaking sunsets that create a lovely backdrop for romantic escapades.
  • Diverse Accommodation: Choose from charming bed and breakfasts to comfortable hotels, ensuring a pleasant stay for every traveller.

Find great hotels near Sherwood

Discover a delightful range of accommodation options in Sherwood, Maryland, from charming bed and breakfasts to comfortable hotels. Ideal for every traveller, these lodgings offer essential amenities such as free Wi-Fi, pet-friendly policies, and meeting rooms. Whether you seek adventure or a relaxing beach holiday, Sherwood's hotels cater to your every need, ensuring a memorable stay in this picturesque locale.

  • St Michaels Inn: Nestled 9.7km from Sherwood, St Michaels Inn offers a vibrant adventure-themed experience for travellers seeking both leisure and business opportunities. This hotel boasts an array of adventure sports and recreational activities, making it the perfect base for those looking to explore the great outdoors. Guests can enjoy nearby fishing, hiking, and biking, or rent a bicycle for their own explorations. With its emphasis on adventure, St Michaels Inn ensures a memorable stay for active visitors.
  • Rod 'N' Reel Resort: Situated 20.9km from Sherwood, the Rod 'N' Reel Resort is a welcoming haven for nature enthusiasts and the LGBTQIA community. This 3-star resort embodies a nature-themed experience, offering a range of adventure sports both onsite and nearby. Guests can embark on boat tours, enjoy kayaking, or take advantage of the fish cleaning table. The resort's commitment to inclusivity and adventure makes it an excellent choice for those looking to connect with nature while enjoying a warm, welcoming atmosphere.
  • The Tidewater Inn: Located 20.9km from Sherwood, The Tidewater Inn is a charming spa-themed retreat that caters to both business travellers and adventure seekers. This 3-star hotel features a full-service spa, offering various treatments including deep tissue massages and facials, ensuring ultimate relaxation after a day of exploration. Guests can indulge in nearby activities such as sailing, hiking, and kayaking, or unwind by the pool. The Tidewater Inn seamlessly blends relaxation with adventure, making it an ideal choice for a rejuvenating stay.

Where to stay near Sherwood

Sherwood, Maryland, offers a delightful blend of outdoor adventures and romantic escapes. Visitors can explore the scenic beauty of the Eastern Shore, enjoy local hangouts with friendly people, and take in stunning river views. As the sun sets, the atmosphere transforms, providing a perfect backdrop for relaxation and family-friendly activities. Discover historical gems and experience the warmth of Sherwood's community, making your vacation truly memorable.

  • St. Michaels: Nestled approximately 8.0km from Sherwood, St. Michaels is a charming waterfront town that beautifully balances relaxation and exploration. Known for its romantic ambiance, visitors flock here particularly in April and during the summer months of June and July. The outdoor experiences are abundant, with a scenic boardwalk that invites leisurely strolls and recreational areas perfect for family outings. Highlights include the picturesque beaches and serene lakes, making it an ideal spot for those looking to unwind and connect with nature.
  • Tilghman: Located about 6.4km from Sherwood, Tilghman is a delightful retreat that showcases stunning natural scenery. The peak travel months from June to August attract those seeking outdoor adventures and romantic getaways. The town offers a variety of recreational activities, including cosy boardwalks that promise captivating views. With its nearby beaches and family-friendly lakes, Tilghman is perfect for visitors eager to soak up the sun and enjoy tranquil waterside moments.
  • Bozman: Just 4.8km away from Sherwood, Bozman is an inviting destination that caters to those with a taste for adventure and romance. Although its visitor numbers vary throughout the year, peak times in March and June to July see a lively atmosphere. Popular activities in Bozman include educational outdoor experiences and recreational areas that appeal to all ages. Local attractions such as beautiful beaches and significant monuments provide an enriching backdrop to your exploration, ensuring memorable experiences for all travellers.

Things to do near Sherwood

Sherwood, Maryland, is perfect for outdoor and romantic adventures, offering a variety of activities such as vibrant shopping centres and recreational areas. Visitors can enjoy outdoor seating, live music, and relaxing by the beach with comfortable chairs. This charming locale provides an ideal setting for a memorable getaway, combining leisure with entertainment for an enjoyable experience.

Shopping

Saint Michaels Village, located 9.7km from Sherwood, offers a charming shopping experience with a blend of city, family, and business vibes. If you're up for a drive, the Bay Bridge Market Place Shopping Center, 19.7km away, boasts entertainment and family-friendly options.

Recreation

Experience a round of golf at Hog Neck Golf Course, where stunning landscapes and outdoor vibes await you. For ultimate relaxation, indulge in soothing treatments at Talbot Massage. Finally, immerse yourself in the arts at the Ballet Theater of Maryland, where culture and entertainment come alive.

Adventure

Explore the St Michaels Nature Trail, a scenic path offering adventure and outdoor vibes a mere 8.0km from Sherwood. For family fun, visit Chesapeake Beach Water Park, located 20.9km away, where exciting slides and pools await. Alternatively, embrace the thrill of sailing at Annapolis Sailing School, 25.7km from Sherwood.

Nightlife

Experience a vibrant night in Sherwood with a visit to the Avalon Theatre for a romantic cultural evening, or enjoy family fun at the Annapolis Bowl arcade. For a cinematic escape, head to Regal Waugh Chapel for a delightful film experience that caters to all ages.

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

Booking tips and Expedia advantages for Sherwood

To save money on your trip to Sherwood, plan your visit between January and March when accommodation prices are lower, avoiding the pricier months of June and September to October. Aim to book your stay on a Tuesday for the best rates. Use Expedia’s search tool to compare prices and explore package deals that combine hotels with flights and activities. Additionally, consider utilising public transport to keep travel costs down, and look for free local attractions to enhance your experience without breaking the bank.

  • 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: Utilise Expedia’s search tool to refine your choices based on your budget, preferred location, and desired type of accommodation. To discover the most affordable prices and special offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Sherwood hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Sherwood

Sherwood, Maryland, offers a perfect blend of outdoor adventure and romantic escapes. Visitors can explore a range of attractions including history museums, a charming marina, and urban parks. These points of interest cater to travellers seeking cultural experiences and family-friendly activities, making Sherwood an ideal destination for those looking to immerse themselves in nature and history.

  • Easton Rail Depot: A charming historic site located 22.5km from Sherwood, Easton Rail Depot offers a glimpse into the area's rich railway history. Its cultural vibes are enhanced by the beautifully restored architecture and engaging exhibits that tell the story of rail transport in the region.
  • Chesapeake Bay Maritime Museum: Situated 9.7km away, this maritime museum immerses visitors in the maritime heritage of the Chesapeake Bay. With captivating exhibits and scenic waterfront views, it showcases the region’s rich fishing and boating traditions.
  • Tilghman Watermen’s Museum: Just 6.4km from Sherwood, this museum celebrates the lives and stories of local watermen. Visitors can explore the unique cultural heritage and history of those who have worked the waters of the Bay for generations.

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

When planning your visit to Sherwood, Maryland, you have several airport options. Washington, DC (DCA-Ronald Reagan Washington National) is located 62.8km away, with nearby 5-star hotels such as Salamander Washington DC and Riggs Washington DC both within 4.8km. Transportation services are readily available to the airport from these hotels. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is 54.7km from Sherwood, offering luxurious options like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km away, with shuttle services. Lastly, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) is 83.7km distant, featuring accommodations like Courtyard by Marriott Salisbury, just 9.7km 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 traveler data. Two other choices for your visit to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Sherwood.
If I need to cancel my hotel reservation in Sherwood, will I receive a refund?
Yes, most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sherwood.
What's the best pet-friendly place to stay in Sherwood?
Lowes Wharf Marina Inn is a top inn for people traveling 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. Features free self parking, an indoor pool, and complimentary wireless internet access. Hyatt Regency Chesapeake Bay and The Westin Annapolis are a couple of other choices that feature an onsite 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 accommodations to choose from. Find out more about Sherwood.
What should I do while I'm visiting Sherwood?
A couple of favorite 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. Check out what more to see and do in Expedia's Sherwood guide.
What's the weather like in Sherwood?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for Sherwood is 53 inches.