Holiday Homes in Sherwood

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Sherwood holiday homes

Marina

Holiday Home in Cambridge

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is €327
includes taxes & fees
18 Mar - 19 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Dining

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is €363
includes taxes & fees
8 Apr - 9 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €226
includes taxes & fees
16 Mar - 17 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is €226
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Pool

Holiday Home in Chesapeak beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €376
includes taxes & fees
17 Mar - 18 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Outdoor dining

Holiday Home in Dorchester County

Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is €255
includes taxes & fees
12 Apr - 13 Apr
Sunset Breezes - quiet waterfront retreat
Fridge, microwave, oven, stovetop

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is €239
includes taxes & fees
14 Mar - 15 Mar
Waterfront Getaway with Dock
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is €324
includes taxes & fees
18 Mar - 19 Mar
Walk to Beach! King Bed & Free Beach Passes
Smart TV

Holiday Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is €451
includes taxes & fees
16 Mar - 17 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 €415
includes taxes & fees
15 Mar - 16 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Beach

Holiday Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is €382
includes taxes & fees
17 Mar - 18 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Outdoor dining

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is €366
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach nearby, sun-loungers, beach towels

Holiday Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is €453
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Smart TV, books

Holiday Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is €342
includes taxes & fees
31 Mar - 1 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is €445
includes taxes & fees
16 Mar - 17 Mar
Cute bungalow blocks to Stadium
Smart TV

Holiday Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is €385
includes taxes & fees
15 Mar - 16 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Outdoor spa tub

Holiday Home in Edgewater

London Towne Bungalow w/Loft - Walk to the Beach!
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is €442
includes taxes & fees
13 Apr - 14 Apr
London Towne Bungalow w/Loft - Walk to the Beach!
Interior

Holiday Home in Shady Side

Sunset Cottage - West River Access and Views!
The price is €362
includes taxes & fees
17 Mar - 18 Mar
Sunset Cottage - West River Access and Views!
Interior

Holiday Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Marina

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is €280
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The property was beautiful, Customer Service was exceptional, the food at the restaurant was delicious, and the room in the barn building was beautiful. My family and I will definitely be returning!"
Jamila 1-night trip
Posted 1 hour ago
The Inn at Chesapeake Bay Beach Club

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
388
Accommodation
593 Holiday Homes
Lowest Price
€226
Highest Price
€453