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Sherwood Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

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

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

Holiday Rental House
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, holiday rental in Sherwood
Landon Cottage is in the waterfront village of Sherwood on  Eastern Shore of MD, holiday rental in Sherwood
Landon Cottage is in the waterfront village of Sherwood on  Eastern Shore of MD, holiday rental in Sherwood

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

Holiday Rental House
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!, holiday rental in Sherwood
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!, holiday rental in Sherwood
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!, holiday rental in Sherwood

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Retreat with HUGE Water Views!!, holiday rental in Sherwood
Private Retreat with HUGE Water Views!!, holiday rental in Sherwood
Private Retreat with HUGE Water Views!!, holiday rental in Sherwood

Private Retreat with HUGE Water Views!!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Chase Away the Chill with Our Winter Stay Specials!, holiday rental in Sherwood
Chase Away the Chill with Our Winter Stay Specials!, holiday rental in Sherwood
Chase Away the Chill with Our Winter Stay Specials!, holiday rental in Sherwood

Chase Away the Chill with Our Winter Stay Specials!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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SEPT SUMMERS &  FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, holiday rental in Sherwood
SEPT SUMMERS &  FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, holiday rental in Sherwood
SEPT SUMMERS &  FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING, holiday rental in Sherwood

SEPT SUMMERS & FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING

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

Waterfront-Private 153 acre Historic Estate

Holiday Rental House
11 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Heated pool, sandy beach, pier, and playground set punch point apart!, holiday rental in Sherwood
Heated pool, sandy beach, pier, and playground set punch point apart!, holiday rental in Sherwood
Heated pool, sandy beach, pier, and playground set punch point apart!, holiday rental in Sherwood

Heated pool, sandy beach, pier, and playground set punch point apart!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD, holiday rental in Sherwood
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD, holiday rental in Sherwood
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD, holiday rental in Sherwood

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

Holiday Rental House
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, holiday rental in Sherwood
Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Sherwood
Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Sherwood

Relaxing Waterfront Cottage Near St Michaels, Maryland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hurry, reserve your stay for 
Summer & Fall of 2025
STR #22-30, holiday rental in Sherwood
Hurry, reserve your stay for 
Summer & Fall of 2025
STR #22-30, holiday rental in Sherwood
Hurry, reserve your stay for 
Summer & Fall of 2025
STR #22-30, holiday rental in Sherwood

Hurry, reserve your stay for Summer & Fall of 2025 STR #22-30

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private, holiday rental in Sherwood
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private, holiday rental in Sherwood
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private, holiday rental in Sherwood

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels with Brand New Pier!, holiday rental in Sherwood
Eastern Shore Getaway Near St. Michaels with Brand New Pier!, holiday rental in Sherwood
Eastern Shore Getaway Near St. Michaels with Brand New Pier!, holiday rental in Sherwood

Eastern Shore Getaway Near St. Michaels with Brand New Pier!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Sherwood
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Sherwood
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Sherwood

SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!

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

Perfect Waterview Cottage - St. Michaels Getaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront  - pier & acreage to run & play.   Pet friendly Oct/Nov dates open!, holiday rental in Sherwood
Waterfront  - pier & acreage to run & play.   Pet friendly Oct/Nov dates open!, holiday rental in Sherwood
Waterfront  - pier & acreage to run & play.   Pet friendly Oct/Nov dates open!, holiday rental in Sherwood

Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quaint Tilghman Island home, holiday rental in Sherwood
Quaint Tilghman Island home, holiday rental in Sherwood
Quaint Tilghman Island home, holiday rental in Sherwood

Quaint Tilghman Island home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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4-Bedroom Retreat: Modern, Pet-Friendly, holiday rental in Sherwood
4-Bedroom Retreat: Modern, Pet-Friendly, holiday rental in Sherwood
4-Bedroom Retreat: Modern, Pet-Friendly, holiday rental in Sherwood

4-Bedroom Retreat: Modern, Pet-Friendly

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, holiday rental in Sherwood
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, holiday rental in Sherwood
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, holiday rental in Sherwood

BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Middle Point Cabin in Saint Michaels, holiday rental in Sherwood
The Middle Point Cabin in Saint Michaels, holiday rental in Sherwood
The Middle Point Cabin in Saint Michaels, holiday rental in Sherwood

The Middle Point Cabin in Saint Michaels

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tilghman | Fenced Yard | Pet Friendly | Charming, holiday rental in Sherwood
Tilghman | Fenced Yard | Pet Friendly | Charming, holiday rental in Sherwood
Tilghman | Fenced Yard | Pet Friendly | Charming, holiday rental in Sherwood

Tilghman | Fenced Yard | Pet Friendly | Charming

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

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

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

Eastern Shore Waterside Cottage Near St. Michaels

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BOOK NOW FOR FALL & WINTER DATES., holiday rental in Sherwood
BOOK NOW FOR FALL & WINTER DATES., holiday rental in Sherwood
BOOK NOW FOR FALL & WINTER DATES., holiday rental in Sherwood

BOOK NOW FOR FALL & WINTER DATES.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Best rates of the season, book today!, holiday rental in Sherwood
Best rates of the season, book today!, holiday rental in Sherwood
Best rates of the season, book today!, holiday rental in Sherwood

Best rates of the season, book today!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tilghman | Pool | Private Dock | Pet Friendly, holiday rental in Sherwood
Tilghman | Pool | Private Dock | Pet Friendly, holiday rental in Sherwood
Tilghman | Pool | Private Dock | Pet Friendly, holiday rental in Sherwood

Tilghman | Pool | Private Dock | Pet Friendly

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Private Dock | Kayaks, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Private Dock | Kayaks, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Private Dock | Kayaks, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Private Dock | Kayaks

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

Grandview - Main House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, holiday rental in Sherwood
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, holiday rental in Sherwood
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub, holiday rental in Sherwood

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre, holiday rental in Sherwood
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre, holiday rental in Sherwood
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre, holiday rental in Sherwood

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre

Holiday Rental House
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, holiday rental in Sherwood
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, holiday rental in Sherwood
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, holiday rental in Sherwood

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik, holiday rental in Sherwood
Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik, holiday rental in Sherwood
Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik, holiday rental in Sherwood

Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Tilghman Waterfront | Indoor Pool | Private Dock | Pool House, holiday rental in Sherwood
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House, holiday rental in Sherwood
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House, holiday rental in Sherwood

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Downtown St. Michaels | Pool | Hot Tub, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Hot Tub, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Pool | Hot Tub, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Pool | Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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"Point of View" Waterfront cottage with panoramic views on Tilghman Island, holiday rental in Sherwood
"Point of View" Waterfront cottage with panoramic views on Tilghman Island, holiday rental in Sherwood
"Point of View" Waterfront cottage with panoramic views on Tilghman Island, holiday rental in Sherwood

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil 3BR Retreat with BBQ & Bikes, holiday rental in Sherwood
Tranquil 3BR Retreat with BBQ & Bikes, holiday rental in Sherwood
Tranquil 3BR Retreat with BBQ & Bikes, holiday rental in Sherwood

Tranquil 3BR Retreat with BBQ & Bikes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy getaway! Centrally located between St. Michaels and Tilghman Island, holiday rental in Sherwood
Cozy getaway! Centrally located between St. Michaels and Tilghman Island, holiday rental in Sherwood
Cozy getaway! Centrally located between St. Michaels and Tilghman Island, holiday rental in Sherwood

Cozy getaway! Centrally located between St. Michaels and Tilghman Island

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning, holiday rental in Sherwood
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning, holiday rental in Sherwood
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning, holiday rental in Sherwood

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Minutes from Downtown St. Michaels | Private Boat Ramp | Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock, holiday rental in Sherwood
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock, holiday rental in Sherwood

Minutes from Downtown St. Michaels | Private Boat Ramp | Dock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy the beautiful reflections of sunsets and the golden leaves on the water!, holiday rental in Sherwood
Enjoy the beautiful reflections of sunsets and the golden leaves on the water!, holiday rental in Sherwood
Enjoy the beautiful reflections of sunsets and the golden leaves on the water!, holiday rental in Sherwood

Enjoy the beautiful reflections of sunsets and the golden leaves on the water!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Come Get Cozy by the Fire, holiday rental in Sherwood
Come Get Cozy by the Fire, holiday rental in Sherwood
Come Get Cozy by the Fire, holiday rental in Sherwood

Come Get Cozy by the Fire

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Duck Cove Waterfront Cottage, holiday rental in Sherwood
Duck Cove Waterfront Cottage, holiday rental in Sherwood
Duck Cove Waterfront Cottage, holiday rental in Sherwood

Duck Cove Waterfront Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tilghman Island Retreat By Knapps Narrows!, holiday rental in Sherwood
Tilghman Island Retreat By Knapps Narrows!, holiday rental in Sherwood
Tilghman Island Retreat By Knapps Narrows!, holiday rental in Sherwood

Tilghman Island Retreat By Knapps Narrows!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront St Michaels Vacation Rental w/ Fire Pit, holiday rental in Sherwood
Waterfront St Michaels Vacation Rental w/ Fire Pit, holiday rental in Sherwood
Waterfront St Michaels Vacation Rental w/ Fire Pit, holiday rental in Sherwood

Waterfront St Michaels Vacation Rental w/ Fire Pit

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Escape The Winter Blues & Book Today, holiday rental in Sherwood
Escape The Winter Blues & Book Today, holiday rental in Sherwood
Escape The Winter Blues & Book Today, holiday rental in Sherwood

Escape The Winter Blues & Book Today

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-49 of 49
Frequently Asked Questions about Sherwood