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Cottages, Villas, Apartments in Sherwood
Holiday Rentals
USA
Maryland (MD)
Talbot County
Cottages, Villas, Apartments in Sherwood
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Internet or Wifi (48)
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Kid friendly (48)
Pet friendly (18)
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Waterfront (33)
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49 rentals
in Sherwood.
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
40
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!
1
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Private Retreat with HUGE Water Views!!
1
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 12
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Chase Away the Chill with Our Winter Stay Specials!
7
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 12
Match:
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SEPT SUMMERS & FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING
46
Holiday Rental House
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5 bedrooms
7 bathrooms
Sleeps 10
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Waterfront-Private 153 acre Historic Estate
3
Holiday Rental House
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11 bedrooms
7 bathrooms
Sleeps 12
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Heated pool, sandy beach, pier, and playground set punch point apart!
2
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD
18
Holiday Rental House
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8 bedrooms
10 bathrooms
Sleeps 12
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The following properties within 20 miles of Sherwood match all your filters:
Relaxing Waterfront Cottage Near St Michaels, Maryland
62
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Hurry, reserve your stay for Summer & Fall of 2025 STR #22-30
73
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
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Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private
23
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 8
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Eastern Shore Getaway Near St. Michaels with Brand New Pier!
37
Holiday Rental House
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1 bedroom
2 bathrooms
Sleeps 2
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SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Perfect Waterview Cottage - St. Michaels Getaway
97
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Quaint Tilghman Island home
1
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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4-Bedroom Retreat: Modern, Pet-Friendly
6
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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The Middle Point Cabin in Saint Michaels
12
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 4
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Tilghman | Fenced Yard | Pet Friendly | Charming
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Secluded Waterfront Property on 3 acres with swimming pool and dock.
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Eastern Shore Waterside Cottage Near St. Michaels
19
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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BOOK NOW FOR FALL & WINTER DATES.
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Sleeps
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Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Best rates of the season, book today!
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Tilghman | Pool | Private Dock | Pet Friendly
10
Holiday Rental House
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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 House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Minutes from Downtown St. Michaels | Private Dock | Kayaks
7
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Grandview - Main House
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 9
Match:
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
2
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre
8
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
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Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
5
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
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Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
6
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 12
Match:
Sleeps
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Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
Holiday Rental House
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3 bedrooms
5 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Minutes from Downtown St. Michaels | Pool | Hot Tub
8
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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"Point of View" Waterfront cottage with panoramic views on Tilghman Island
7
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Tranquil 3BR Retreat with BBQ & Bikes
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cozy getaway! Centrally located between St. Michaels and Tilghman Island
2
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
4
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Sleeps
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Enjoy the beautiful reflections of sunsets and the golden leaves on the water!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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Come Get Cozy by the Fire
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Duck Cove Waterfront Cottage
5
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Tilghman Island Retreat By Knapps Narrows!
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Waterfront St Michaels Vacation Rental w/ Fire Pit
4
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
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Escape The Winter Blues & Book Today
3
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Sleeps
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1
Showing results 1-49 of 49
Frequently Asked Questions about Sherwood
Do any holiday rentals in Sherwood have a pool?
Yes, here are some popular holiday rentals in Sherwood that have a pool:
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!
See all holiday rentals with a pool in Sherwood on Tripadvisor
Do any holiday rentals in Sherwood have internet access?
Yes, here are some popular holiday rentals in Sherwood that have internet access:
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!
See all holiday rentals in Sherwood on Tripadvisor
What are the best pet friendly rentals in Sherwood?
The best pet friendly rentals in Sherwood are:
SEPT SUMMERS & FREE BUSHEL OF CRABS W/SEPT/OCT BOOKING
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
See all pet friendly holiday rentals in Sherwood on Tripadvisor
What are some great rentals in Sherwood that are kid friendly?
Some of the most popular kid friendly rentals in Sherwood are:
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Sailor Joe's | Lovely and serene-the perfect spot to nurture your soul!
Private Retreat with HUGE Water Views!!
See all kid friendly holiday rentals in Sherwood on Tripadvisor
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