Sherwood holiday rentals

We found 185 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:6 Nov - 13 Nov

screened porch
Pool
Dining table- seats 10!
View from Pier back to house!
Exceptional
(145 reviews)

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

Easton

8% off
AU$11,251
for 7 nights, 1 home
AU$1,607 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
"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
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Exceptional
(161 reviews)

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

Sherwood

10% off
AU$3,167
for 7 nights, 1 home
AU$452 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Exterior
Exterior
Living area
Private kitchen
Exceptional
(64 reviews)

Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay

Cambridge

8% off
AU$11,169
for 7 nights, 1 home
AU$1,596 per night
includes taxes & fees
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,10% off 7day stay
Sit and stay a while!
View down the lane
Living Room with flat screen TV and sleeper sofa
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,881
for 7 nights, 1 cottage
AU$412 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Private kitchen
Dining
Living area
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

12% off
AU$4,519
for 7 nights, 1 cottage
AU$646 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Living area
Be ready to float! Bring your own inner tubes and tennis shoes!
Interior
Exterior detail
Exceptional
(143 reviews)

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

Bozman

12% off
AU$2,953
for 7 nights, 1 cottage
AU$422 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Private kitchen
Living area
Living area
Property grounds
Exceptional
(5 reviews)

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman

8% off
AU$3,168
for 7 nights, 1 cottage
AU$453 per night
includes taxes & fees
Lovely 2-bedroom waterfront cottage in charming Wittman
Dining
Exterior
Living area
Property grounds
Exceptional
(19 reviews)

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

Tilghman

8% off
AU$4,176
for 7 nights, 1 cottage
AU$597 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Interior
Living area
Living area
Terrace/patio
Exceptional
(7 reviews)

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

St. Michaels

17% off
AU$3,399
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Dining
Outdoor dining
upstairs offers 2 bedrooms including 1 queen and 4 twin (bunks)
fridge with ice maker
Exceptional
(30 reviews)

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt

8% off
AU$3,414
for 7 nights, 1 cottage
AU$488 per night
includes taxes & fees
Eastern Shore Waterside Cottage Near St. Michaels
Private kitchen
Living area
Interior
Exterior
Exceptional
(49 reviews)

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

Stevensville

8% off
AU$9,321
for 7 nights, 1 home
AU$1,332 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Exterior
Exterior
Private kitchen
Living area
Exceptional
(27 reviews)

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

Cambridge

8% off
AU$6,742
for 7 nights, 1 home
AU$963 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Large screened porch with ceiling fan allows outdoor dining and relaxing.
St. Michaels Harbor from Park down street
Front and side view of Blades House from Locust St.
Park half block from house
Exceptional
(150 reviews)

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

St. Michaels

8% off
AU$4,138
for 7 nights, 1 cottage
AU$591 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

  • 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)
  • Easton Cycle and Sport (13.9 mi / 22.3 km)
  • Hog Neck Golf Course (14.8 mi / 23.8 km)
  • Phillips Wharf Environmental Center (3.2 mi / 5.1 km)
  • Talbot Massage (13.8 mi / 22.1 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)
  • Romancoke Wharf County Park (8.3 mi / 13.3 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 most popular type of holiday home accommodation in Sherwood?
Houses are the most popular type of holiday home in Sherwood, according to our data. Even if you have a different idea about what you'd like, Stayz has properties in many shapes and sizes. Compare our options to find your perfect pad.
How much does it cost to rent a holiday home in Sherwood?
The average price for a holiday home in Sherwood can vary depending on factors including property type, season and length of stay. Whether you're looking for a sprawling villa with lots of bedrooms or a quaint cottage just enough for two, just enter your dates of travel to view stays that offer great value.
How much does it cost to rent a beach house in Sherwood?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Enter your Sherwood travel dates to see your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want.
Are there pet-friendly holiday homes in Sherwood?
Yes. You'll find six stays that welcome pets in Sherwood on Stayz. Our furry kids deserve a break too, so simply use our search function for pet-friendly holiday homes to book a place where your pooch can lap up the good times.
Can I rent a house with a pool in Sherwood?
Dig out your swimsuit and inflatable swan, because there are five houses with a private pool in Sherwood. Stay at one of these terrific holiday homes and every day can be a pool day. Simply enter your dates into Stayz, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Sherwood?
When it comes to home amenities that guests are on the lookout for in Sherwood, a garden, a fireplace and a water view rank the highest. With Stayz holiday homes, you'll enjoy choices to suit your taste and style, whether you're planning to get away with family, friends or even pets.
Are there large group holiday homes in Sherwood?
Choose from five holiday homes in Sherwood that can host 10 or more guests. Whether you're organising a get-together with extended family or a special event like a birthday party, there's ample room to get your loved ones together under the same roof.
Are there holiday homes in Sherwood that welcome kids?
Bring the entire group together for an adventure in Sherwood at one of our six family-friendly properties. Many of these stays come with conveniences that are suitable for trips with the kids, such as full kitchens, living rooms and entertainment units. Simply check the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Sherwood?
There are loads of amazing things to see and do with the family in Sherwood, including:
  • Chesapeake Bay Maritime Museum
  • St. Michaels Museum
  • Tilghman Watermen's Museum
Are there holiday homes with WiFi in Sherwood?
Whether you'd like to keep up with the news, make a video call or surf social networks, there are four holiday homes with WiFi in Sherwood. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Sherwood?
There are six holiday homes with air conditioning in Sherwood providing that cool, cool breeze and extra element of comfort. Simply enter your preferred travel dates and then use our handy filters to find properties with air conditioning.
How old do you have to be to rent a holiday home in Sherwood?
The minimum age is normally 16, 18 or 21. It can vary from one property to another on Stayz, so look at the rules of your chosen Sherwood holiday home before you book.
How long can I rent a holiday home in Sherwood for?
It really depends on the Sherwood property. To view a list of options offering extended stays, just enter your travel dates and number of people into Stayz's search page. You can look forward to having the property to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a backyard where your little ones can play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.