Holiday Homes in Sherwood

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Sherwood holiday homes

Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €228
includes taxes & fees
28 Jan - 29 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
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 clean, and very comfortable beds."
United States
Edward R.
The price is €293
includes taxes & fees
2 Feb - 3 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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 €216
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop

Holiday Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is €311
includes taxes & fees
27 Jan - 28 Jan
Beautiful Waterfront Retreat in Cambridge!
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is €263
includes taxes & fees
26 Jan - 27 Jan
Walk to Beach! King Bed & Free Beach Passes
Interior

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €436
includes taxes & fees
26 Jan - 27 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is €367
includes taxes & fees
26 Jan - 27 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51 reviews)
"Great place, will stay again"
United States
Matt S.
The price is €238
includes taxes & fees
27 Jan - 28 Jan
Waterfront Getaway with Dock
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 €359
includes taxes & fees
26 Jan - 27 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV, fireplace, table football, ping pong

Holiday Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is €385
includes taxes & fees
27 Jan - 28 Jan
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
The price is €309
includes taxes & fees
2 Feb - 3 Feb
Cozy 2br home w/ parking in downtown Annapolis
TV, books, offices

Holiday Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is €473
includes taxes & fees
28 Jan - 29 Jan
Holly Hill Haven - Sleeps 10
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 €413
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 €374
includes taxes & fees
1 Feb - 2 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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 €410
includes taxes & fees
26 Jan - 27 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is €431
includes taxes & fees
26 Jan - 27 Jan
Cute bungalow blocks to Stadium
Outdoor spa tub

Holiday Home in Edgewater

London Towne Bungalow w/Loft - Walk to the Beach!
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is €411
includes taxes & fees
9 Feb - 10 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
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.
The price is €586
includes taxes & fees
26 Jan - 27 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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.
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is €439
includes taxes & fees
26 Jan - 27 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

10/10 Excellent
"Food was fresh, great verity. Staff was amazing, very nice , great customer service and amazing personalities!!! "
Mandy 2-night trip
Posted 2 days ago
Hampton Inn & Suites Annapolis

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
395
Accommodation
592 Holiday Homes
Lowest Price
€216
Highest Price
€586