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Sherwood Rentals

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14 Houses

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,113

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Price per night from

$514

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$351

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$857

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$217

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$296

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$430

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$381

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$319

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$217

Main House at Grandview at Pleasure Point

Bozman house

4 bedrooms / 3 bathrooms / sleeps 9

“Family Fun at Grandview” Our group of grandparents, children with spouses, & grandchildren spent a week in the main house at Grandview. We had a great time in the pool, on the docks, in the porches, & exploring this very large & private property. We also enjoyed the shopping, restaurants, & Maritime Museum in St. Michaels. It was a very hot week & the many fans that were provided made it comfortable. The kitchen was well equipped to handle a large group & we had a great seafood feast on the picnic tables by the pool.

Price per night from

$545

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$714

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,884

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Neavitt manor house

25 bedrooms / 25 bathrooms / sleeps 50

Price per night from

$8,532

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