Vacation rentals in Sherwood

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Top-rated vacation rentals in Sherwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Aug 16 – 23

$173 per night
Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 418 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

Mar 19 – 26

$180 per night
Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Aug 16 – 23

$108 per night

Popular amenities for Sherwood vacation rentals

Other great vacation rentals in Sherwood

Guest favorite

Home in Saint Michaels

4.97 out of 5 average rating, 238 reviews

Miles Aweigh

Aug 12 – 19

$419 per night
Guest favorite

Home in Saint Michaels

4.91 out of 5 average rating, 151 reviews

Small Historic House Downtown St Michaels

Dec 21 – 28

$167 per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 reviews

Calico Cottage Guest House, king bed, free parking

Nov 14 – 21

$85 per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

$417 per night
Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 530 reviews

“Cabana by the Bay”-tiny home on a pier!

Mar 20 – 27

$124 per night
Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 176 reviews

Guest House: Farm homestead

Jul 3 – 10

$109 per night
Superhost

Bungalow in Deale

4.86 out of 5 average rating, 353 reviews

Cozy waterfront getaway on the Bay

Jan 24 – 31

$158 per night
Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

May 1 – 8

$168 per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 29 – Dec 6

$73 per night
Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 103 reviews

Historic Downtown in-law suite

Jan 9 – 16

$106 per night
Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 195 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Oct 18 – 25

$108 per night
Superhost

Home in Bozman

5.0 out of 5 average rating, 5 reviews

Grace Creek Cottage

May 22 – 29

$328 per night

Destinations to explore

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