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Sherwood Holiday Rentals

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50 rentals in Sherwood.
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Holidays at the Cove  - plenty of space to gather while making memories, holiday rental in Sherwood

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in Sherwood

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, holiday rental in Sherwood

New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Sherwood

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Sherwood

Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday rental in Sherwood

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!, holiday rental in Sherwood

TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, holiday rental in Sherwood

Beautiful Tidewater home between Easton & ST Michaels!

4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Cottage, holiday rental in Sherwood

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach., holiday rental in Sherwood

Enhanced Cleaning & Disinfecting. Private Beach Volleyball Court. Walk to Beach.

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Fully remodel 2 bedroom country cottage., holiday rental in Sherwood

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Sherwood

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in Sherwood

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples, holiday rental in Sherwood

The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax in Tilghman Island, holiday rental in Sherwood

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront, Water All Around, Peaceful Family Getaway, holiday rental in Sherwood

Waterfront, Water All Around, Peaceful Family Getaway

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, holiday rental in Sherwood

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Sherwood

Bayfront Home with Amazing Rooftop Deck!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton, holiday rental in Sherwood

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, holiday rental in Sherwood

407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax in our cottage within walking distance of Herrington on the Bay events., holiday rental in Sherwood

Relax in our cottage within walking distance of Herrington on the Bay events.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, holiday rental in Sherwood

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Sherwood

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Spot Cottage on the Bay, holiday rental in Sherwood

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, holiday rental in Sherwood

Location Location! St Michaels-- In Town Cottage!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, holiday rental in Sherwood

*****Waterfront home w/ pool in St. Michaels

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, holiday rental in Sherwood

Premier Cottage in St. Michaels- In Town Location!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Sherwood

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday rental in Sherwood

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, holiday rental in Sherwood

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

7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Sherwood

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Private waterfront estate with pool, convenient to Easton and St. Michaels, holiday rental in Sherwood

Private waterfront estate with pool, convenient to Easton and St. Michaels

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!, holiday rental in Sherwood

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, holiday rental in Sherwood

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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KI Golf House-A PAR for the Course & Mile to Beach, holiday rental in Sherwood

KI Golf House-A PAR for the Course & Mile to Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterview Cottage In St. Michaels!, holiday rental in Sherwood

Waterview Cottage In St. Michaels!

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, holiday rental in Sherwood

Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX, holiday rental in Sherwood

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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St. Michael's Premier in Town Summer Cottage now with private pool!, holiday rental in Sherwood

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, holiday rental in Sherwood

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, holiday rental in Sherwood

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Property, Kayaks, Private Dock, Near Town, holiday rental in Sherwood

Waterfront Property, Kayaks, Private Dock, Near Town

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, holiday rental in Sherwood

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, holiday rental in Sherwood

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Easton Waterfront Property, holiday rental in Sherwood

Tranquil Easton Waterfront Property

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina, holiday rental in Sherwood

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Ship's Cove Inn and Resort, holiday rental in Sherwood

Ship's Cove Inn and Resort

6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Kent Island House with Pool and Bay Views!, holiday rental in Sherwood

Kent Island House with Pool and Bay Views!

3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Newly-managed Waterfront Kent Island home, holiday rental in Sherwood

Newly-managed Waterfront Kent Island home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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New! Stunning Waterfront with pool for Naval Academy families!, holiday rental in Sherwood

New! Stunning Waterfront with pool for Naval Academy families!

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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