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

Sherwood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Sherwood vacation rentals

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ￥12,723
￥44,058 total
includes taxes & fees
Nov 1 - Nov 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

2. 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 ￥22,877
￥51,175 total
includes taxes & fees
Oct 30 - Oct 31
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A house with a yellow door and a window with a lamp outside.

3. 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 ￥22,909
￥55,294 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Living area

4. 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 ￥16,635
￥54,254 total
includes taxes & fees
Nov 1 - Nov 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

5. 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 ￥30,749
￥81,292 total
includes taxes & fees
Nov 16 - Nov 17
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

6. 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 ￥14,313
￥45,656 total
includes taxes & fees
Nov 2 - Nov 3
Charming Coastal/Country Home w/3 Acres & Sauna!
A marina with floating homes, docks, and boats.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (110 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

8. 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 ￥28,399
￥72,123 total
includes taxes & fees
Nov 1 - Nov 2
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

9. 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 ￥26,979
￥59,533 total
includes taxes & fees
Nov 8 - Nov 9
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A deck with a view of a marina, including boats and docks.

10. 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 ￥15,799
￥44,315 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A dining area with a wooden spiral staircase, a round table with chairs, a chandelier, and a clock on the wall.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (4 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

12. 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 ￥38,946
￥75,279 total
includes taxes & fees
Oct 30 - Oct 31
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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
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 ￥14,988
￥50,914 total
includes taxes & fees
Oct 30 - Oct 31
Cambridge Apt in Walkable Neighborhood
A hot tub with a white deck and railing, surrounded by trees and a house 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 ￥30,571
￥75,916 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

15. 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 ￥31,554
￥71,063 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!
A two-story house with a red roof, a brick chimney, and a small porch.

16. 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 house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...
United States
Michele F.
The price is ￥113,594
￥166,232 total
includes taxes & fees
Oct 30 - Oct 31
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Living area

17. 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 ￥35,498
￥66,894 total
includes taxes & fees
Nov 3 - Nov 4
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A living room with two grey sofas, a coffee table, and a ceiling fan.

18. 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 traveler
The price is ￥10,413
￥51,903 total
includes taxes & fees
Oct 30 - Oct 31
Cambridge Apt in Walkable Neighborhood
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

19. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is ￥35,498
￥42,979 total
includes taxes & fees
Nov 27 - Nov 28
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Three birds perched on a wooden structure by the water.

20. 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 ￥126,058
￥218,718 total
includes taxes & fees
Nov 1 - Nov 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Our stay was much better than I was expecting! The area was very quiet and the staff friendly and helpful. Continental breakfast was your standard fare and everything clean."
Bobbi 2-night trip
Posted 2 hours ago
St Michaels Inn

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
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  • 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 vacation rental in Sherwood?

Yes, you can find vacation rentals close to popular attractions in Sherwood, or you can go with a more secluded option if you'd like a relaxing place to stay. Sherwood is known for its waterfront and restaurants.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Sherwood vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Sherwood?

With 6 Expedia vacation rentals, you're sure 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 larger area, you’ll find Knapp's Narrows Marina & Inn and St. Michaels Winery.

What are vacation rentals like in Sherwood?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Sherwood. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.