Sherwood Forest holiday rentals

We found 680 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Sherwood Forest that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Sherwood Forest

Showing deals for:13 Nov - 20 Nov

Kitchen - Granite Island
Terrace/patio
The Green Bedroom View
Great Room
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,308
for 7 nights, 1 home
AU$2,044 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Exterior
Marina
The kitchen opens up to a spacious sitting room complete with large flat screen tv and fireplace.
Additional dining area off of the living room
Exceptional
(37 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
AU$9,029
for 7 nights, 1 home
AU$1,290 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
Room
Private kitchen
Outdoor dining
Interior
Exceptional
(20 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$8,184
for 7 nights, 1 home
AU$1,169 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Sitting area overlooking Burley Creek
Enjoy screened in porch with dining table and sitting area
Lawn for yard games along the waterfront, or simply relax in the shade
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(60 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off
AU$7,328
for 7 nights, 1 home
AU$1,047 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Exterior
Interior
Exterior
Private kitchen
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$5,959
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
LARGE OPEN KITCHEN
SCREENED PORCH
PUBLIC BEACH/PARK 2 MILES AWAY
DINING ROOM SEATS 10-14 W/LEAFS
Exceptional
(44 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

12% off
AU$8,465
for 7 nights, 1 home
AU$1,209 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Dining
Private kitchen
Exterior
Dining
Excellent
(8 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,057
for 7 nights, 1 home
AU$722 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Dining
Terrace/patio
Private kitchen
Exterior
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,197
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Interior
Pool
Living area
Exterior
Exceptional
(230 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,592
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Interior
Private kitchen
Living area
Living area
Exceptional
(12 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

7% off
AU$10,525
for 7 nights, 1 home
AU$1,504 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Living area
Pool
Exterior
Screen porch for relaxing, eating, watching the water, working on a laptop
Exceptional
(57 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

16% off
AU$4,746
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
outdoor space
Terrace/patio
Living room with wood fireplace and second TV with basic channels
Marina
Exceptional
(91 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
AU$5,354
for 7 nights, 1 home
AU$765 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Twin size sofa/futon for a 3rd person.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Room
Separate entryway with electronic keypad.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

8% off
AU$2,476
for 7 nights, 1 apartment
AU$354 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Interior
Private kitchen
Dining
Living area
Exceptional
(11 reviews)

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Riva

21% off
AU$4,042
for 7 nights, 1 home
AU$577 per night
includes taxes & fees
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Interior
Living area
Living area
Living area
Exceptional
(10 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
AU$5,773
for 7 nights, 1 home
AU$825 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Open floor plan
Primary bedroom has king bed
Exterior
Exceptional
(58 reviews)

Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience

Annapolis

6% off
AU$7,085
for 7 nights, 1 home
AU$1,012 per night
includes taxes & fees
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Living area
Dining
Private kitchen
Exterior
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$6,700
for 7 nights, 1 home
AU$957 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Exceptional
(7 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
AU$3,453
for 7 nights, 1 home
AU$493 per night
includes taxes & fees
Cozy Cottage with Beach Access
Dining and Work Space
Exterior
Adirondack Chairs to Enjoy the Wooded Preserve
Fully Loaded Kitchen with Island Seating
Exceptional
(13 reviews)

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

Annapolis

12% off
AU$2,692
for 7 nights, 1 home
AU$385 per night
includes taxes & fees
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4
Property grounds
Exterior
Room
Living area
Exceptional
(267 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
AU$1,671
for 7 nights, 1 cottage
AU$239 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Living Room with Cable Television
Historic Annapolis and City Dock
Rear Entry and Rooftop Balcony
Quaint Pinkney Street
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,168
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Room
Private kitchen
Dining
Living area
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

7% off
AU$6,981
for 7 nights, 1 home
AU$997 per night
includes taxes & fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Fully equipped and filled with light, the kitchen opens to the backyard for easy outdoor dining.
The upstairs primary suite includes a queen bed and private bath with a deep soaking tub—your own peaceful hideaway.
Dining
Whether curling up with a book or logging into a Zoom call, this light-filled space is both calm and versatile.
Exceptional
(6 reviews)

Unique and central in Eastport

Annapolis

7% off
AU$4,062
for 7 nights, 1 home
AU$580 per night
includes taxes & fees
Unique and central in Eastport
Kitchen with island
String lights on the patio make it the perfect place to unwind in the evening!
Welcome!
Kitchen Island
Exceptional
(20 reviews)

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Annapolis

8% off
AU$7,566
for 7 nights, 1 home
AU$1,081 per night
includes taxes & fees
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
  • 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

Book a holiday rental for your Sherwood Forest getaway

Learn about the unique charm of Sherwood Forest with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Sherwood Forest

Are you hoping to find things to do while you're in the area? Venture out of your holiday home and experience everything that makes Sherwood Forest a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Maryland Renaissance Festival (3.2 mi / 5.2 km)
  • Thanksgiving Farm Wines (11.8 mi / 19 km)
  • Severna Park Golf Center (1.9 mi / 3.1 km)
  • Bay Hills Golf Club (3.7 mi / 6 km)
  • U.S. Naval Academy Golf Club (4.8 mi / 7.7 km)
  • South River Golf Links (7.7 mi / 12.4 km)

Exploring the natural features in Sherwood Forest

Whether you're looking for adventure or just want to appreciate the scenery, Sherwood Forest is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (6.3 mi / 10.1 km)
  • Sandy Point Beach (8.1 mi / 13 km)
  • Northern Chesapeake Bay (11.5 mi / 18.5 km)
  • Patuxent River (16.8 mi / 27.1 km)
  • Spa Creek (4.7 mi / 7.6 km)
  • Sparrows Beach (6.2 mi / 9.9 km)

Travelling to and around Sherwood Forest

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 12.3 mi (19.8 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Baltimore Washington International Airport (BWI), which is 12.5 mi (20 km) away.

Frequently asked questions

What is the best area to stay in Sherwood Forest when booking a holiday rental?
When looking for a holiday rental in Sherwood Forest, Maryland, you might consider the charming neighbourhoods that surround this picturesque area. One of the most appealing options is the nearby community of Edgewater, which boasts a delightful blend of natural beauty and local attractions. Here, visitors can enjoy the scenic views of the Chesapeake Bay and explore the expansive Broadneck Park, great for outdoor enthusiasts and families alike.Another great choice is the vibrant town of Annapolis, just a short drive away. Known for its rich maritime history, Annapolis offers visitors the chance to wander through its historic district, where you can admire beautifully preserved buildings and indulge in a variety of shops and restaurants. The United States Naval Academy is also a must-visit, featuring stunning architecture and fascinating tours.In terms of holiday rentals, the area around Sherwood Forest offers a range of properties, providing options to suit different preferences and budgets.
What are the top attractions in Sherwood Forest?
In Sherwood Forest, Maryland, visitors can enjoy a range of natural attractions and recreational activities. The area is primarily known for its scenic waterfront views along the Chesapeake Bay. The nearby Broadneck Park offers expansive green spaces, playgrounds, and sports facilities, making it a great spot for families and outdoor enthusiasts.For those interested in history and culture, the historic district of Annapolis is just a short drive away, where you can explore the Maryland State House and the U.S. Naval Academy, both rich in American history. Additionally, the tranquil waters of the bay provide opportunities for boating and fishing, with public docks available for easy access.
Are all fees included in the Sherwood Forest 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 Forest holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sherwood Forest 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 Forest holiday homes?
You can find great discounts on holiday homes in Sherwood Forest 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 Forest holiday home booking on Stayz?
To find Sherwood Forest 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 Forest?
A long-stay holiday home in Sherwood Forest 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 Forest holiday home?
Book your Sherwood Forest 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 Forest?
Prices for holiday homes in Sherwood Forest 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 Forest 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.

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