Sherwood Forest holiday homes

We found 681 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:20 Nov - 27 Nov

Living room
Kitchen
Upper level master bedroom
Kitchen
Exceptional
(16 reviews)

House near Patapsco River 2700 square feet

Pasadena

8% off
NZ$7,239
for 7 nights, 1 home
NZ$1,034 per night
includes taxes & fees
House near Patapsco River 2700 square feet
Exterior
Terrace/patio
Kitchen - Granite Island
The Green Bedroom View
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
NZ$17,105
for 7 nights, 1 home
NZ$2,444 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
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
Beautiful waterfront home on Burley Creek with private pier
Exceptional
(62 reviews)

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

Annapolis

8% off
NZ$9,231
for 7 nights, 1 home
NZ$1,319 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Private kitchen
Interior
Exterior
Interior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
NZ$7,239
for 7 nights, 1 home
NZ$1,034 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
NZ$11,394
for 7 nights, 1 home
NZ$1,628 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Living area
Private kitchen
Living area
Interior
Exceptional
(12 reviews)

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

Annapolis

8% off
NZ$15,590
for 7 nights, 1 home
NZ$2,227 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Dining
Private kitchen
Exterior
Living area
Excellent
(9 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
NZ$6,159
for 7 nights, 1 home
NZ$880 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Private kitchen
Terrace/patio
Exterior
Living area
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
NZ$3,846
for 7 nights, 1 home
NZ$549 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Screen porch for relaxing, eating, watching the water, working on a laptop
Pool
Dining
Exterior
Exceptional
(57 reviews)

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

Annapolis

15% off
NZ$5,818
for 7 nights, 1 home
NZ$831 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
outdoor space
Terrace/patio
upstairs bedroom w/ King size bed and space for queen air mattress
Living room with wood fireplace and second TV with basic channels
Exceptional
(91 reviews)

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

Pasadena

8% off
NZ$6,521
for 7 nights, 1 home
NZ$932 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Separate entryway with electronic keypad.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Local artwork is displayed and for sale, if you wish to take a memory home.
Room
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

8% off
NZ$2,909
for 7 nights, 1 apartment
NZ$416 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Living area
Living area
Interior
Dining
Exceptional
(10 reviews)

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

Riva

8% off
NZ$7,018
for 7 nights, 1 home
NZ$1,003 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
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).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Comfortable family room with reclining sofa, Smart TV and remote controlled window shades.
Exceptional
(8 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
NZ$5,554
for 7 nights, 1 home
NZ$793 per night
includes taxes & fees
Cozy Cottage with Beach Access
Primary bedroom has king bed
Open floor plan
Gourmet Kitchen with seating at the counter for 5
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Exceptional
(58 reviews)

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

Annapolis

6% off
NZ$8,575
for 7 nights, 1 home
NZ$1,225 per night
includes taxes & fees
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Property grounds
Exterior
Living area
Room
Exceptional
(267 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
NZ$2,012
for 7 nights, 1 cottage
NZ$287 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Dining
The upstairs primary suite includes a queen bed and private bath with a deep soaking tub—your own peaceful hideaway.
Fully equipped and filled with light, the kitchen opens to the backyard for easy outdoor 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

8% off
NZ$7,038
for 7 nights, 1 home
NZ$1,005 per night
includes taxes & fees
Unique and central in Eastport
Quaint Pinkney Street
Historic Annapolis and City Dock
Ship's Ladder Stairs to Rooftop Deck
Rear Entry and Rooftop Balcony
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
NZ$5,110
for 7 nights, 1 home
NZ$730 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Dining room with space for 6
Updated kitchen with all major appliances
Private, fenced outdoor space
Comfortable and cozy living room with fireplace (for aesthetic only), Smart TV, comfortable seating, games/puzzles, and books.
Exceptional
(8 reviews)

Timeless Charm Meets Modern Comfort

Annapolis

7% off
NZ$6,083
for 7 nights, 1 home
NZ$869 per night
includes taxes & fees
Timeless Charm Meets Modern Comfort
Water view from the kitchen
Property grounds
Interior
Private kitchen
Exceptional
(31 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
NZ$8,385
for 7 nights, 1 home
NZ$1,198 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Living area
Terrace/patio
Dining
Back yard and fire pit
Exceptional
(47 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
NZ$7,689
for 7 nights, 1 home
NZ$1,098 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
Exterior detail
Private kitchen
Interior
Exterior detail
Wonderful
(14 reviews)

18th Cent. Charm in Historic Downtown Annapolis

Annapolis

16% off
NZ$3,312
for 7 nights, 1 apartment
NZ$473 per night
includes taxes & fees
18th Cent. Charm in Historic Downtown Annapolis
Walking distance to gate 3
City Dock
Lounging room, Roku tv
Kitchen/lounging/dining room
Exceptional
(34 reviews)

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis

8% off
NZ$5,696
for 7 nights, 1 home
NZ$814 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
Dining table seats 6 comfortable, 8 if you want to get friendly!
Property grounds
Waterfront park one block away
Less than 1/2 mile to the newly rebuilt Annapolis Yacht Club
Exceptional
(76 reviews)

Beautifully Renovated Historic District Home

Annapolis

5% off
NZ$8,812
for 7 nights, 1 home
NZ$1,259 per night
includes taxes & fees
Beautifully Renovated Historic District Home
Renovated kitchen with all major appliances and supplies
Renovated kitchen with all major appliances and supplies
Stylish half-bathroom with heated floors
Dining room with seating for 6 and electric fireplace
Exceptional
(21 reviews)

Newly renovated in DTA w parking

Annapolis

8% off
NZ$8,251
for 7 nights, 1 home
NZ$1,179 per night
includes taxes & fees
Newly renovated in DTA w parking
  • 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)
  • Walden Golf Club (7 mi / 11.3 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

How much does it cost to rent a holiday home in Sherwood Forest?
Different factors can influence what you'll pay for your holiday home in Sherwood Forest, including the type of property, season and length of stay. But, all our holiday homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Sherwood Forest?
The average price for a holiday home close to the beach in Sherwood Forest depends on when you're travelling and the type and size of property you're looking for. You can quickly and easily find prices on Bookabach by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a pool.
What are the top attractions for families in Sherwood Forest?
Keeping the kids occupied during your stay in Sherwood Forest is a cinch with these exciting family-friendly attractions:
  • Annapolis Maritime Museum
  • Sandy Point Beach
  • Annapolis Sailing School
How old do you have to be to rent a holiday home in Sherwood Forest?
The minimum age allowed can vary across properties on Bookabach, so be sure to check the rules of the holiday home in Sherwood Forest you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Sherwood Forest for?
The amount of time you can rent a Sherwood Forest holiday home for varies depending on the property. Just tap in your preferred travel dates to view options offering longer term stays. They have all you need to make your extended trip more enjoyable and comfortable, such as air conditioning and kitchens. Some properties might also offer discounted weekly or monthly prices, so you can hang around longer for less.

More holiday ideas