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Check prices for these dates

Next weekend
19 Sept - 21 Sept
In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Browse Select Sherwood Holiday Homes

Our top choices for Sherwood holiday homes

The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

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

9.6 out of 10, Exceptional, (8)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Riverfront Retreat 7mil from MD Renaissance Fest!
Exterior

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"It was a beautiful and private setting for a family reunion."
Riverfront Retreat 7mil from MD Renaissance Fest!
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Dining

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (29)
"It was great!"
Charming Historic Townhouse Steps From USNA
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is £262
includes taxes & fees
15 Sept - 16 Sept
Cozy 2br home w/ parking in downtown Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (28)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Beautiful 2-bedroom water view house in Annapolis
Fridge, microwave, oven, stovetop

Beautiful 2-bedroom water view house in Annapolis

10.0 out of 10, Exceptional, (1)
"We had such an amazing stay!! House was beautiful and had everything we needed. View of the water was absolutely incredible and greatly enhanced our time there. Also, such a short walk to the beach! Kevin was an amazing host! He was very responsive and accommodating!! Highly recommend this house for a relaxing getaway!"
Beautiful 2-bedroom water view house in Annapolis
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (14)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,332
includes taxes & fees
22 Sept - 23 Sept
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Outdoor pool

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (82)
"Clean and nice place to stay"
Walk to Everything House
25-50% Off~Private Beach~Hot Tub~Fire Table~
Terrace/patio

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (28)
"Cute little cottage with great views and very comfortable for a small family. "
25-50% Off~Private Beach~Hot Tub~Fire Table~
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (14)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is £292
includes taxes & fees
7 Oct - 8 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (53)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Beach nearby, sun-loungers, beach towels

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room

9.8 out of 10, Exceptional, (28)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Timeless Charm Meets Modern Comfort
Fridge, microwave, oven, stovetop

Timeless Charm Meets Modern Comfort

10.0 out of 10, Exceptional, (2)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
Timeless Charm Meets Modern Comfort
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis
Exterior

Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

10.0 out of 10, Exceptional, (24)
"Absolutely enjoyed our stay. Wonderful access to the Yard and DTA. Home is clean, well equipped, and very functional."
Historic & sunny home w/ Fireplace steps from USNA & 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

Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Check in easy, breakfast very good, staff very good, rooms updated and clean, some tlc needed but overall a good place to stay, convenient to everything. Bathroom fan should have separate switch, very loud, air conditioner loud also. Thats about it. Nice job Best Western "
Philip 1-night trip
Posted 5 days ago
Best Western Annapolis

Find out more about Sherwood

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
728
Accommodation
649 Holiday Homes
Lowest Price
£262
Highest Price
£1,332

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