Vacation Rentals in Sherwood, MD: Compare 10+ Sites & Save

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102 Best Vacation Rentals in Sherwood (Starting from $175)

Sailor Joes
Sailor Joes
House
Sherwood, MD, USA
1.9k from Sherwood center

Security/Safety, Parking, Internet, Child Friendly

1 Bedroom6 Guests
New to Booking
$632
Average price / night
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ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
House
Sherwood, MD, 21665, United States
0.8k from Sherwood center

AC, Arcade, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms10 Guests
9.8

Exceptional

40 reviews

$1363
Average price / night
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Mill Point
Mill Point
House
Neavitt, MD, USA
2.9k from Sherwood center

Parking, Pool, Security/Safety, Internet, Pet Friendly, Child Friendly

1 Bedroom10 Guests
New to Booking
$1199
Average price / night
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
House
Sherwood, MD, 21665, United States
1.0k from Sherwood center

AC, Arcade, Barbecue, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater

8 Bedrooms12 Guests
10.0

Exceptional

37 reviews

$1991
Average price / night
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Waterfront Bliss- Ultimate Tilghman Retreat home
Waterfront Bliss- Ultimate Tilghman Retreat home
House
MD, USA
3.2k from Sherwood center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$683
Average price / night
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Heated pool, sandy beach, pier, and playground set punch point apart!
Heated pool, sandy beach, pier, and playground set punch point apart!
House
Sherwood, MD, 21665, United States
1.1k from Sherwood center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1263
Average price / night
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Tilghman Island Retreat By Knapps Narrows!
Tilghman Island Retreat By Knapps Narrows!
House
MD, USA
3.3k from Sherwood center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
8.0

Good

1 reviews

$274
Average price / night
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Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
House
Sherwood, MD, 21665, United States
1.3k from Sherwood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

150 reviews

$332
Average price / night
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Crepe Myrtle
Crepe Myrtle
House
Tilghman, MD, USA
3.6k from Sherwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$572
Average price / night
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6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
House
Sherwood, MD, 21665, United States
1.7k from Sherwood center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$1239
Average price / night
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Tranquil Waters
Tranquil Waters
House
Tilghman, MD, USA
3.6k from Sherwood center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1897
Average price / night
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Amazing Waterfront Views, Private Pool and Dock
Amazing Waterfront Views, Private Pool and Dock
House
Sherwood, MD, 21665, United States
2.3k from Sherwood center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
New to Booking
$1404
Average price / night
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Neavitt Cottage
Neavitt Cottage
House
Neavitt, MD, USA
4.1k from Sherwood center

Parking, Security/Safety, Internet, Pet Friendly, Child Friendly

1 Bedroom8 Guests
New to Booking
$765
Average price / night
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Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
House
Sherwood, MD, 21665, United States
2.7k from Sherwood center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$537
Average price / night
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Clearview
Clearview
House
Tilghman Island, MD, USA
4.3k from Sherwood center

Parking, Pool, Security/Safety, Hot Tub, Internet, Wellness Facilities, Pet Friendly

1 Bedroom6 Guests
New to Booking
$765
Average price / night
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Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
House
Bozman, MD, 20815, United States
2.9k from Sherwood center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$1138
Average price / night
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St Michaels Area Cottage - Walk to Water and Marina
St Michaels Area Cottage - Walk to Water and Marina
House
Neavitt, MD, USA
4.5k from Sherwood center

Internet, Pet Friendly, Parking, Kitchen, Wheelchair Accessible, Child Friendly

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$175
Average price / night
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Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities
Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities
House
Tilghman Island, MD, 21671, United States
3.1k from Sherwood center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$311
Average price / night
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The Weekender
The Weekender
House
Mount Pleasant, MD, USA
5.6k from Sherwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$441
Average price / night
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Tilghman | Pool | Private Dock | Pet Friendly
Tilghman | Pool | Private Dock | Pet Friendly
House
Tilghman, MD, 21671, United States
3.2k from Sherwood center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms8 Guests
New to Booking
$782
Average price / night
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Dragonfly Cove
Dragonfly Cove
House
Mount Pleasant, MD, USA
5.9k from Sherwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
New to Booking
$590
Average price / night
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Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
House
Bozman, MD, 21612, United States
3.2k from Sherwood center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

95 reviews

$598
Average price / night
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Brand-New Pool! Waterfront Bozman Village Home
Brand-New Pool! Waterfront Bozman Village Home
House
MD, USA
6.0k from Sherwood center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs

4 Bedrooms8 Guests
New to Booking
$494
Average price / night
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BOOK NOW FOR SPRING & SUMMER DATES.
BOOK NOW FOR SPRING & SUMMER DATES.
House
Tilghman Island, MD, 21671, United States
3.2k from Sherwood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.6

Exceptional

49 reviews

$499
Average price / night
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Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD
Cottage 1A-Charming 1-bedroom cottage on the water, minutes from St Michaels MD
Cottage
Bozman, MD, 21612, United States
3.3k from Sherwood center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

6 reviews

$311
Average price / night
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GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD
House
Bozman, MD, 21612, United States
3.3k from Sherwood center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$682
Average price / night
Check Availability
Pet-Friendly Summer Retreat on Tilghman
Pet-Friendly Summer Retreat on Tilghman
House
Tilghman Island, MD, 21671, United States
3.4k from Sherwood center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

12 reviews

$315
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Sherwood.

Stay Near Sherwood's Top Attractions

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Sherwood Vacation Rentals on the Map

Frequently Asked Questions

You can explore 102 verified vacation rentals in Sherwood. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Sherwood vary depending on the season, property size, and location. Rates typically start from around $175 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Sherwood include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Sherwood welcome pets. Currently, 30 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Sherwood often include amenities such as Internet, Fireplace/Heating, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.