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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Sherwood holiday rentals

Exterior

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, (49 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$1,069
HK$2,583 total
includes taxes & fees
12 Aug - 13 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby

2. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is HK$1,491
HK$3,603 total
includes taxes & fees
1 Sept - 2 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

3. 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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is HK$2,863
HK$5,861 total
includes taxes & fees
25 Aug - 26 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,069
HK$2,657 total
includes taxes & fees
13 Aug - 14 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
Coffee/tea maker, fridge, microwave, oven

5. Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is HK$2,169
HK$5,638 total
includes taxes & fees
3 Aug - 4 Aug
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Exterior detail

6. 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 HK$981
HK$2,522 total
includes taxes & fees
10 Aug - 11 Aug
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
TV, offices

7. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,898
HK$5,436 total
includes taxes & fees
3 Aug - 4 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
Dining

8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is HK$1,961
HK$3,284 total
includes taxes & fees
3 Aug - 4 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

9. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 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 HK$2,682
HK$4,852 total
includes taxes & fees
10 Aug - 11 Aug
Sunset Cottage - West River Access and Views!
Dining

10. Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
The price is HK$2,470
HK$4,720 total
includes taxes & fees
5 Aug - 6 Aug
Chic retreat steps to Water, Piers & Waterfront Park
Smart TV

11. 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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$3,589
HK$6,048 total
includes taxes & fees
31 Aug - 1 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Pool

12. 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)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,521
HK$4,036 total
includes taxes & fees
1 Sept - 2 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach nearby, sun-loungers, beach towels

13. 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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,823
HK$5,462 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Exterior

14. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,137
HK$3,590 total
includes taxes & fees
12 Aug - 13 Aug
Plum Point Cottage #17
Terrace/patio

15. 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
The price is HK$1,320
HK$2,872 total
includes taxes & fees
10 Aug - 11 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Marina

16. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,352
HK$3,803 total
includes taxes & fees
10 Aug - 11 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Outdoor pool, a heated pool

17. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (86 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,921
HK$3,612 total
includes taxes & fees
2 Sept - 3 Sept
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

18. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (10 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is HK$1,514
HK$4,345 total
includes taxes & fees
3 Aug - 4 Aug
Renovated Bungalow | Walk to Beach | Dog-Friendly
Interior

19. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,404
HK$4,282 total
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

20. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is HK$3,129
HK$6,008 total
includes taxes & fees
5 Aug - 6 Aug
Charming Annapolis WaterVIEW Home
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Perfectly located within the historical district walking distance to multiple options as well as restaurants and shop"
Anne 4-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Sherwood

Search for holiday rentals in Sherwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Sherwood using one of the methods below:

  • View our selection of featured holiday rentals in Sherwood
  • Use the map to find apartments and other holiday homes in the Sherwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sherwood while they last

Look no further and take a look at our great range of rental properties in Sherwood!

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.