Sherwood holiday rentals

We found 183 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Sherwood that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Sherwood

Showing deals for:27 Nov - 4 Dec

View from Pier back to house!
Pool
Dining table- seats 10!
View from Foyer into Great Room
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$10,964
for 7 nights, 1 home
AU$1,566 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Another view from above.
The view off of the point, breathtaking.
Interior
Pool
Exceptional
(45 reviews)

Grandview- Main House

Bozman

25% off
AU$6,639
for 7 nights, 1 home
AU$948 per night
includes taxes & fees
Grandview- Main House
Property grounds
Exterior
Living area
Private kitchen
Exceptional
(21 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,055
for 7 nights, 1 cottage
AU$579 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Rear Porch for relaxing or for barbecues!
View of Side of Harrison House and St. Michaels Harbor from Locust Street
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Thomas Harrison House looking from St. Michaels Town Harbor
Exceptional
(143 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$7,542
for 7 nights, 1 home
AU$1,077 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
Delightful front garden welcomes you when approaching house from driveway
Convenient open-concept design: kitchen, dining and living areas
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,074
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Private kitchen
Dining
Interior
Living area
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,228
for 7 nights, 1 cottage
AU$604 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Exterior
Living area
Private kitchen
Dining
Exceptional
(49 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
AU$8,988
for 7 nights, 1 home
AU$1,284 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Living Room with flat screen TV and sleeper sofa
View down the lane
Sit and stay a while!
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,799
for 7 nights, 1 cottage
AU$400 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Family Room for reading, playing games, watching television, or just relaxing.
Front of W Melson House
Large Screened Porch with rocking chairs
Eating Area adjacent Kitchen
Exceptional
(208 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels

8% off
AU$4,355
for 7 nights, 1 cottage
AU$622 per night
includes taxes & fees
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Room
Living area
Terrace/patio
Living area
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
AU$3,409
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Interior
Living area
Exceptional
(144 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,866
for 7 nights, 1 cottage
AU$409 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Large screened porch with ceiling fan allows outdoor dining and relaxing.
St. Michaels Harbor from Park down street
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
Front and side view of Blades House from Locust St.
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$4,018
for 7 nights, 1 cottage
AU$574 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Private kitchen
Exterior
Exterior
Dining
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,708
for 7 nights, 1 home
AU$958 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to scenic Sherwood

The island views and riverfront create a pretty picture of Sherwood. This scenic and welcoming city entices travellers with its sailing and restaurants. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Sherwood

Are you searching for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sherwood has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (5.4 mi / 8.7 km)
  • Chesapeake Beach Water Park (12.6 mi / 20.3 km)
  • Paul Reed Smith Guitars (15.6 mi / 25.2 km)
  • Phillips Wharf Environmental Center (3.2 mi / 5.1 km)
  • Talbot Massage (13.8 mi / 22.1 km)
  • Easton Cycle and Sport (13.9 mi / 22.3 km)

Exploring the natural features in Sherwood

Whether you're looking for adventure or just want to take in the scenery, Sherwood is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Bay Environmental Center (13.8 mi / 22.2 km)
  • Northern Chesapeake Bay (14.1 mi / 22.7 km)
  • Breezy Point Beach (14.3 mi / 23 km)
  • Bay Ridge Beach (14.8 mi / 23.9 km)
  • Maryland Quiet Waters Park (15.9 mi / 25.5 km)
  • Shadyside Park (12.1 mi / 19.5 km)

Travelling to and around Sherwood

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 14.1 mi (22.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 52.1 mi (83.8 km) away.

Frequently asked questions

What is the best area to stay in Sherwood when booking a holiday rental?
When considering a holiday rental in Sherwood, Maryland, a popular area to stay in is the nearby neighbourhood of Columbia. This vibrant community offers a diverse selection of properties, ranging from charming apartments to spacious family homes, making it suitable for various types of travellers. Columbia is known for its picturesque parks and well-planned infrastructure, providing a pleasant environment for relaxation and exploration.A highlight of staying in this area is the proximity to the Merriweather Post Pavilion, a renowned outdoor concert venue that hosts a variety of musical performances throughout the year. Additionally, the Columbia Mall is a fantastic destination for shopping and dining, featuring a wide range of shops and eateries to suit every taste. The scenic Lake Kittamaqundi, with its walking paths and lovely views, is also a great spot to unwind and enjoy the outdoors.
Where are the best areas for renting a beach house in Sherwood?
For renting a beach house in Sherwood, Maryland, travellers should focus on the nearby Chesapeake Bay area, particularly the communities of Kent Island and the surrounding waterfront spots. These locations offer a variety of beach houses that provide easy access to sandy shores and picturesque views of the bay. Many properties in this region come equipped with modern amenities such as spacious decks for outdoor dining, private docks for boating enthusiasts, and fully stocked kitchens ideal for family meals.In Kent Island, holiday rentals often feature features like large living areas with panoramic windows, allowing guests to enjoy the waterfront scenery. Some houses also include amenities like hot tubs and fire pits, great for relaxing evenings after a day spent on the beach. The area is known for its charming coastal vibe, with local shops and seafood restaurants nearby, enhancing the overall experience.Additionally, the nearby Sandy Point State Park offers opportunities for hiking, picnicking, and swimming, making it a great spot for outdoor activities. Rentals close to this park may provide easy access to nature trails and beach access, often featuring outdoor showers and grills for convenient summer cookouts.
What is the most popular type of holiday rental accomodation in Sherwood?
In Sherwood, holiday houses are the most popular type of holiday rental, with about 21 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many of these homes also offer outdoor spaces such as gardens or patios, where guests can relax and enjoy the pleasant surroundings.
Are there any family house rentals in Sherwood?
In Sherwood, Maryland, there are several family-friendly house rentals available, making it a great choice for those looking to accommodate larger groups. These homes often come with spacious living areas, kitchens equipped for cooking family meals, and outdoor spaces where children can play safely.Nearby, visitors can explore local parks and recreational areas, superb for family outings, while the vibrant communities in the surrounding region offer various dining and shopping options.
Can I rent a holiday home with a pool or hot tub in Sherwood?
In Sherwood, Maryland, there are several holiday homes available for rent that come equipped with pools and hot tubs. This charming area offers a mix of suburban comfort and natural beauty, making it an appealing destination for travellers seeking relaxation. Many of the rentals feature private pools, hot tubs, and spacious outdoor areas, great for family gatherings or entertaining friends. Inside, guests can expect fully equipped kitchens, comfortable living spaces, and amenities like Wi-Fi and air conditioning to enhance their stay.
Are there any remote work holiday rentals in Sherwood?
In Sherwood, Maryland, there are several remote work holiday rentals available, with about 21 options to choose from. Many of these properties are well-equipped to cater to the needs of remote workers, offering amenities such as free Wi-Fi, dedicated office spaces, desks, and even computer monitors in some units. This makes it easy for professionals to maintain productivity while enjoying a change of scenery.The area is also known for its tranquil surroundings, which can provide a nice backdrop for work and relaxation. For those seeking to take breaks, the local parks offer opportunities for outdoor activities, allowing for a refreshing pause from work duties. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sherwood?
In Sherwood, popular holiday rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, and spacious decks or patios for enjoying the outdoors. Many rentals also feature inviting fireplaces, great for cosy evenings after a day of exploration. For those seeking a refreshing dip, private pools are a common highlight, providing a relaxing retreat. Additionally, travellers can expect coffee and tea makers in their accommodations, ensuring a warm beverage is always within reach.
When is the best time to visit Sherwood for a holiday rental?
March marks the beginning of the peak season in Sherwood, attracting visitors eager to enjoy the vibrant springtime atmosphere. The months from March to May offer a delightful experience as the region comes to life with blooming flowers and mild temperatures, superb for those who appreciate outdoor activities and sightseeing.During this period, temperatures typically range from 5 to 20 degrees Celsius, providing a comfortable climate for exploring the scenic beauty of Sherwood. Visitors can enjoy leisurely strolls along the picturesque waterfront, or partake in local festivals that celebrate the arrival of spring, making for memorable experiences close to nature.For those seeking a more budget-friendly option, February presents an excellent opportunity to visit. While it's considered the low season, the charm of Sherwood remains, and you can take advantage of quieter surroundings to explore the area at your own pace. The early signs of spring can already be seen, and the serenity of the season allows for a more intimate connection with the landscape.
What are the top attractions in Sherwood?
In Sherwood, Maryland, visitors can enjoy a serene atmosphere with access to several outdoor attractions. The nearby Patuxent River provides opportunities for kayaking, fishing, and leisurely walks along its banks. The area is also in proximity to the expansive Patuxent River Park, which features hiking trails and picnic spots, ideal for nature enthusiasts.For those interested in history, the nearby town of Upper Marlboro offers historical sites and local charm, including the Prince George's County Courthouse and various quaint shops and eateries. Additionally, Sherwood is conveniently located near the larger city of Laurel, where attractions such as the Laurel Park racetrack and the Montpelier Mansion can be explored.
Are all fees included in the Sherwood holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sherwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sherwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sherwood holiday homes?
You can find great discounts on holiday homes in Sherwood on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sherwood holiday home booking on Stayz?
To find Sherwood holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sherwood?
A long-stay holiday home in Sherwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sherwood holiday home?
Book your Sherwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sherwood?
Prices for holiday homes in Sherwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sherwood to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.