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Sherwood Vacation Rentals

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Bedrooms

Bathrooms

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Suitability

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5 mi
50 rentals in Sherwood.
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, vacation rental in Sherwood
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, vacation rental in Sherwood
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, vacation rental in Sherwood

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Landon Cottage is in the waterfront village of Sherwood on  Eastern Shore of MD, vacation rental in Sherwood
Landon Cottage is in the waterfront village of Sherwood on  Eastern Shore of MD, vacation rental in Sherwood
Landon Cottage is in the waterfront village of Sherwood on  Eastern Shore of MD, vacation rental in Sherwood

Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!, vacation rental in Sherwood
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!, vacation rental in Sherwood
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!, vacation rental in Sherwood

Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Private Retreat with HUGE Water Views!!, vacation rental in Sherwood
Beautiful, Private Retreat with HUGE Water Views!!, vacation rental in Sherwood
Beautiful, Private Retreat with HUGE Water Views!!, vacation rental in Sherwood

Beautiful, Private Retreat with HUGE Water Views!!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun, vacation rental in Sherwood
Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun, vacation rental in Sherwood
Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun, vacation rental in Sherwood

Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Amazing waterfront with new pool., vacation rental in Sherwood
Amazing waterfront with new pool., vacation rental in Sherwood
Amazing waterfront with new pool., vacation rental in Sherwood

Amazing waterfront with new pool.

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood
CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood
CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Rental Home
8 bedrooms
10 bathrooms
Sleeps 12
Match: Sleeps
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Large  waterfront on 15 ac FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, vacation rental in Sherwood
Large  waterfront on 15 ac FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, vacation rental in Sherwood
Large  waterfront on 15 ac FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, vacation rental in Sherwood

Large waterfront on 15 ac FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront-Private 153 acre Historic Estate, vacation rental in Sherwood
Waterfront-Private 153 acre Historic Estate, vacation rental in Sherwood
Waterfront-Private 153 acre Historic Estate, vacation rental in Sherwood

Waterfront-Private 153 acre Historic Estate

Rental Home
11 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, vacation rental in Sherwood

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Rental Home
8 bedrooms
10 bathrooms
Sleeps 12
Match: Sleeps
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The following properties within 20 miles of Sherwood match all your filters:
Relaxing Waterfront Cottage Near St Michaels, Maryland, vacation rental in Sherwood
Relaxing Waterfront Cottage Near St Michaels, Maryland, vacation rental in Sherwood
Relaxing Waterfront Cottage Near St Michaels, Maryland, vacation rental in Sherwood

Relaxing Waterfront Cottage Near St Michaels, Maryland

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, vacation rental in Sherwood
Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, vacation rental in Sherwood
Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, vacation rental in Sherwood

Great prices on a available days left!!! Beautiful Leadenham Creek. STR #22-30

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home with Magnificent Views, vacation rental in Sherwood
Waterfront Home with Magnificent Views, vacation rental in Sherwood
Waterfront Home with Magnificent Views, vacation rental in Sherwood

Waterfront Home with Magnificent Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, vacation rental in Sherwood
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, vacation rental in Sherwood
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, vacation rental in Sherwood

Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, vacation rental in Sherwood
Eastern Shore Getaway Near St. Michaels, vacation rental in Sherwood
Eastern Shore Getaway Near St. Michaels, vacation rental in Sherwood

Eastern Shore Getaway Near St. Michaels

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Sherwood
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Sherwood
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Sherwood

Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, vacation rental in Sherwood
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, vacation rental in Sherwood
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, vacation rental in Sherwood

SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Sherwood
Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Sherwood
Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Sherwood

Perfect Waterview Cottage - St. Michaels Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, vacation rental in Sherwood
Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, vacation rental in Sherwood
Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, vacation rental in Sherwood

Waterfront - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM LANDING

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quaint Tilghman Island home, vacation rental in Sherwood
Quaint Tilghman Island home, vacation rental in Sherwood
Quaint Tilghman Island home, vacation rental in Sherwood

Quaint Tilghman Island home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Offering complimentary wine for August bookings, vacation rental in Sherwood
Offering complimentary wine for August bookings, vacation rental in Sherwood
Offering complimentary wine for August bookings, vacation rental in Sherwood

Offering complimentary wine for August bookings

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Sherwood
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Sherwood
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Sherwood

BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Sherwood
St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Sherwood
St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Sherwood

St. Michaels Area Cottage - Walk to Water & Marina

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Middle Point Cabin in Saint Michaels, vacation rental in Sherwood
The Middle Point Cabin in Saint Michaels, vacation rental in Sherwood
The Middle Point Cabin in Saint Michaels, vacation rental in Sherwood

The Middle Point Cabin in Saint Michaels

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Banyan Cottage | Just the waterman's village charmer you've been looking for!, vacation rental in Sherwood
Banyan Cottage | Just the waterman's village charmer you've been looking for!, vacation rental in Sherwood
Banyan Cottage | Just the waterman's village charmer you've been looking for!, vacation rental in Sherwood

Banyan Cottage | Just the waterman's village charmer you've been looking for!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay, vacation rental in Sherwood
Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay, vacation rental in Sherwood
Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay, vacation rental in Sherwood

Jellyfish Cottage - Spectacular Sunsets over Chesapeake Bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Crepe Myrtle - The peaceful 1.3 acre fully fenced oasis you are looking for!, vacation rental in Sherwood
Crepe Myrtle - The peaceful 1.3 acre fully fenced oasis you are looking for!, vacation rental in Sherwood
Crepe Myrtle - The peaceful 1.3 acre fully fenced oasis you are looking for!, vacation rental in Sherwood

Crepe Myrtle - The peaceful 1.3 acre fully fenced oasis you are looking for!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Waterfront Property on 3 acres with swimming pool and dock., vacation rental in Sherwood
Secluded Waterfront Property on 3 acres with swimming pool and dock., vacation rental in Sherwood
Secluded Waterfront Property on 3 acres with swimming pool and dock., vacation rental in Sherwood

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore Waterside Cottage Near St. Michaels, vacation rental in Sherwood
Eastern Shore Waterside Cottage Near St. Michaels, vacation rental in Sherwood
Eastern Shore Waterside Cottage Near St. Michaels, vacation rental in Sherwood

Eastern Shore Waterside Cottage Near St. Michaels

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House on the Chesapeake Bay, vacation rental in Sherwood
House on the Chesapeake Bay, vacation rental in Sherwood
House on the Chesapeake Bay, vacation rental in Sherwood

House on the Chesapeake Bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Caulk's Cove of St. Michaels, vacation rental in Sherwood
Caulk's Cove of St. Michaels, vacation rental in Sherwood
Caulk's Cove of St. Michaels, vacation rental in Sherwood

Caulk's Cove of St. Michaels

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BOOK NOW FOR A SPRING AND SUMMER GETAWAY., vacation rental in Sherwood
BOOK NOW FOR A SPRING AND SUMMER GETAWAY., vacation rental in Sherwood
BOOK NOW FOR A SPRING AND SUMMER GETAWAY., vacation rental in Sherwood

BOOK NOW FOR A SPRING AND SUMMER GETAWAY.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Neavitt Cottage - Shorely, this is a true outdoor paradise!, vacation rental in Sherwood
Neavitt Cottage - Shorely, this is a true outdoor paradise!, vacation rental in Sherwood
Neavitt Cottage - Shorely, this is a true outdoor paradise!, vacation rental in Sherwood

Neavitt Cottage - Shorely, this is a true outdoor paradise!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Time to make those summer plans!, vacation rental in Sherwood
Time to make those summer plans!, vacation rental in Sherwood
Time to make those summer plans!, vacation rental in Sherwood

Time to make those summer plans!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Clearview - Big Amenities: Pool Hot Tub Amazing Views!, vacation rental in Sherwood
Clearview - Big Amenities: Pool Hot Tub Amazing Views!, vacation rental in Sherwood
Clearview - Big Amenities: Pool Hot Tub Amazing Views!, vacation rental in Sherwood

Clearview - Big Amenities: Pool Hot Tub Amazing Views!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gratitude Farm of Bozman, vacation rental in Sherwood
Gratitude Farm of Bozman, vacation rental in Sherwood
Gratitude Farm of Bozman, vacation rental in Sherwood

Gratitude Farm of Bozman

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, vacation rental in Sherwood
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, vacation rental in Sherwood
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, vacation rental in Sherwood

Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bankors Aweigh - There’s nothing like a St. Michaels Sunrise!, vacation rental in Sherwood
Bankors Aweigh - There’s nothing like a St. Michaels Sunrise!, vacation rental in Sherwood
Bankors Aweigh - There’s nothing like a St. Michaels Sunrise!, vacation rental in Sherwood

Bankors Aweigh - There’s nothing like a St. Michaels Sunrise!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!, vacation rental in Sherwood
Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!, vacation rental in Sherwood
Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!, vacation rental in Sherwood

Covey Creek - Peaceful Waterfront Home, BBQ, Kayak & Fire Pit!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Thorntonwood - Family Fun on Broad Creek, vacation rental in Sherwood
Thorntonwood - Family Fun on Broad Creek, vacation rental in Sherwood
Thorntonwood - Family Fun on Broad Creek, vacation rental in Sherwood

Thorntonwood - Family Fun on Broad Creek

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Grandview - Main House, vacation rental in Sherwood
Grandview - Main House, vacation rental in Sherwood
Grandview - Main House, vacation rental in Sherwood

Grandview - Main House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in Sherwood
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in Sherwood
Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!, vacation rental in Sherwood

Oyster Cottage | Fishing, Crabbing, and Boating Are All at Your Fingertips!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Last guest said property was AMAZING., vacation rental in Sherwood
Last guest said property was AMAZING., vacation rental in Sherwood
Last guest said property was AMAZING., vacation rental in Sherwood

Last guest said property was AMAZING.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!, vacation rental in Sherwood
Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!, vacation rental in Sherwood
Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!, vacation rental in Sherwood

Emily's Lane - Quaint Waterfront Near St. Michaels - Pool, Grill, Game Room!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Sherwood
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Sherwood
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Sherwood

Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Sherwood
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Sherwood
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Sherwood

Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Eventide Farm | Your Unforgettable Waterfront Retreat!, vacation rental in Sherwood
Eventide Farm | Your Unforgettable Waterfront Retreat!, vacation rental in Sherwood
Eventide Farm | Your Unforgettable Waterfront Retreat!, vacation rental in Sherwood

Eventide Farm | Your Unforgettable Waterfront Retreat!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in Sherwood
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in Sherwood
Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, vacation rental in Sherwood

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

Cabin
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Mill Point - Water here, water there, water views from almost everywhere!, vacation rental in Sherwood
Mill Point - Water here, water there, water views from almost everywhere!, vacation rental in Sherwood
Mill Point - Water here, water there, water views from almost everywhere!, vacation rental in Sherwood

Mill Point - Water here, water there, water views from almost everywhere!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Tranquil Water - Looking to getaway, relax and recharge?, vacation rental in Sherwood
Tranquil Water - Looking to getaway, relax and recharge?, vacation rental in Sherwood
Tranquil Water - Looking to getaway, relax and recharge?, vacation rental in Sherwood

Tranquil Water - Looking to getaway, relax and recharge?

Rental Home
7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Sherwood