A large brick house with a green roof, surrounded by lush gardens and trees.

Sherwood Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Sherwood holiday rentals

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$513
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A lighthouse with a white exterior, a balcony, and a metal roof.

2. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is AU$421
includes taxes & fees
5 Nov - 6 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

3. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$426
includes taxes & fees
2 Dec - 3 Dec
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is AU$443
includes taxes & fees
15 Nov - 16 Nov
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A deck with a view of a marina, including boats and docks.

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is AU$369
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

6. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is AU$437
includes taxes & fees
5 Nov - 6 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

7. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is AU$601
includes taxes & fees
5 Nov - 6 Nov
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is AU$595
includes taxes & fees
1 Dec - 2 Dec
Sunset Cottage - West River Access and Views!
A living room with two grey sofas, a coffee table, and a ceiling fan.

9. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is AU$461
includes taxes & fees
5 Nov - 6 Nov
Cambridge Apt in Walkable Neighborhood
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

10. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AU$656
includes taxes & fees
5 Nov - 6 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A deck with outdoor furniture, a red door, and a house with windows.

11. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AU$508
includes taxes & fees
9 Nov - 10 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

12. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is AU$678
includes taxes & fees
1 Dec - 2 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with two grey sofas, a coffee table, and a ceiling fan.

13. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is AU$442
includes taxes & fees
5 Nov - 6 Nov
Cambridge Apt in Walkable Neighborhood
A beach with chairs and a pier in the background.

14. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is AU$650
includes taxes & fees
9 Nov - 10 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Living area

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is AU$568
includes taxes & fees
10 Nov - 11 Nov
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Pool

16. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is AU$568
includes taxes & fees
1 Dec - 2 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A two-story house with a red roof, a brick chimney, and a small porch.

17. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.4 out of 10, Very good, (6 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is AU$1,415
includes taxes & fees
5 Nov - 6 Nov
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

18. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is AU$367
includes taxes & fees
10 Nov - 11 Nov
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A patio with a grill, picnic tables, and umbrellas.

19. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is AU$1,740
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

20. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is AU$559
includes taxes & fees
20 Nov - 21 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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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Top Sherwood Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The rooms were nice, the towels were nice and full. The morning breakfast was perfect enough food and nice coffee. We'll make this our go-to in Annapolis."
Jackie 1-night trip
Posted 8 hours ago
Sonesta ES Suites Annapolis

Find out more about Sherwood

Everything you need to know about Sherwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sherwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherwood holiday rentals we have selected for you start as low as AU$369 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sherwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sherwood?

Yes, there are holiday rentals close to the most popular sights in Sherwood, or you can select a more secluded option if you're looking for a relaxing stay. Sherwood is known for its waterfront and restaurants.

What are some of the best holiday rentals that Sherwood has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Sherwood is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Sherwood?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Sherwood stay.

What can I see and do in Sherwood?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Goat Island. In the wider area, you’ll find Knapp's Narrows Marina & Inn and St. Michaels Winery.

What are holiday rentals like in Sherwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sherwood. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.