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Best Vacation rentals and Airbnb offers in Greensboro, MD
9.4 9 reviews
Greensboro, MD
08/05 – 08/16
$263/nighttotal: $2893 (11 )
Relaxation Haven On The Shore Near Choptank River
2 4
apartment , Greensboro
This Greensboro apartment rental is conveniently located near Tuckahoe State Park, Olive Branch Lodge Park, Adkins Arboretum, and Martinak State Park, all within a 6-10 mile radius. This two-bedroom, one-bathroom unit sleeps six guests and features a fully equipped kitchen, fireplace, washer/dryer, DVD player, and a balcony overlooking the on-site garden, offering easy access to area parks.
9.8 12 reviews
Greensboro, MD
08/05 – 08/16
$496/nighttotal: $5456 (11 )
Turnbridge Manor
5 4
apartment , Denton
This waterfront home is located in downtown Denton, Maryland's Eastern Shore, less than 60 minutes from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. It has earned excellent user ratings for its comfort and amenities. The apartment features 5 bedrooms and 3 bathrooms, comfortably accommodating up to 10 guests. It offers a blend of modern amenities and historic charm, including a garden, parking, internet access, and a fully equipped kitchen.
Greensboro, MD
08/05 – 08/16
$212/nighttotal: $2332 (11 )
The Ridgely House-an Eastern Shore Escape
4 4
apartment , Ridgely
This newly renovated 4-bedroom house is located in Ridgely, Maryland, offering proximity to Tuckahoe State Park and Adkins Arboretum, and a short drive to St. Michaels and Easton. This rental property accommodates up to 6 guests and features a newly renovated kitchen with a dishwasher, air conditioning, complimentary Wi-Fi, and a spacious backyard with bicycles available for guest use.
10 3 reviews
Greensboro, MD
08/05 – 08/16
$238/nighttotal: $2618 (11 )
Relaxation Haven On The Shore By Choptank River
1 4
gîte , Greensboro
This charming cottage in Greensboro, Eastern Shore, offers a tranquil setting amidst nature, despite being close to amenities. With excellent user, location, and cleanliness ratings, it has 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests. The apartment features a fully equipped kitchen, comfortable beds, a cozy living area, and outdoor garden areas for camping, a firepit altar, and meditation or Tai Chi. Guided meditation sessions are available upon request, adding to the apartment's wellness ambiance.
9.9 98 reviews
Greensboro, MD
08/05 – 08/16
$356/nighttotal: $3916 (11 )
Turnbridge Manor - Waterfront Historic House
5 4
apartment , Denton
This waterfront rental is located in downtown Denton, Maryland's Eastern Shore, less than an hour from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. This apartment has received excellent ratings for cleanliness, location, and user experience. This five-bedroom, three-bathroom home can accommodate up to 10 guests. The apartment offers a blend of modern amenities and historic charm, with features like gas fireplaces, multiple outdoor spaces, and a kitchen with a separate entrance.
10 7 reviews
Greensboro, MD
08/05 – 08/16
$316/nighttotal: $3476 (11 )
Frosty Acres Choptank River Farm
1 4
gîte , Greensboro
This Greensboro-area waterfront rental is situated on 60 acres along the Choptank River on Maryland's Eastern Shore, near Ridgely, and boasts a rich history as former land of the Choptank River Native Indians. The three-bedroom, two-bathroom Victorian house sleeps five, offers a private boat launch (up to 25 feet), BBQ facilities, kayaking, fishing, swimming, a designated tent camping area, and walking trails throughout the property.
9.9 107 reviews
Greensboro, MD
08/05 – 08/16
$283/nighttotal: $3113 (11 )
Adorable 2-bedroom Bungalow Near Easton, Denton
1 4
house , Queen Anne
This charming Queen Anne 2-bedroom bungalow is situated in a quiet neighborhood near Easton, Denton, offering easy access to both urban amenities and natural attractions. Just a short drive from Killens Pond Water Park and within a reasonable driving distance of Sandy Point State Park and Chesapeake Exploration Center, this vacation rental boasts excellent user, location, and cleanliness ratings. The bungalow's inviting interior creates a warm and welcoming atmosphere, with a fully equipped kitchen, modern amenities, and a private outdoor space where guests can relax and enjoy the surrounding views. With a floor area of 140 square feet, the bungalow comfortably accommodates up to 4 guests, making it an ideal choice for families or small groups seeking a cozy and convenient vacation rental in Queen Anne.
Wigwam Lodge, a Goldsboro cabin rental near the Choptank River (5 minutes), Denton (20 minutes), and an hour from the beach, offers a convenient location with easy parking. This 1500-square-foot log home features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, jacuzzi, and fast Wi-Fi.
10 28 reviews
Greensboro, MD
08/05 – 08/16
$316/nighttotal: $3476 (11 )
Adorable Two-bedroom Retreat Close To Easton, Denton, Centreville
2 4
apartment , Queen Anne
This Queen Anne vacation home sits 0.7 miles from Tuckahoe State Park and within 9 miles of Adkins Arboretum, Triple Creek Winery, Daniel Crouse Memorial Park, and the Caroline Public Library, offering a peaceful rural retreat. The two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen, private balcony, garden, barbecue grills, and free Wi-Fi; enjoy nearby outdoor recreation and wine tasting.
Greensboro, MD
08/05 – 08/16
$319/nighttotal: $3509 (11 )
Come Stay At Lyford Landing Farm.relax While Being Embraced By Farm Fields.
3 4
cottage , Williston
This 1400 sq ft cottage in Denton is located in a rural area adjacent to a river, offering proximity to the Museum of Rural Life and the Avalon Theatre. This 3-bedroom, 2-bathroom house accommodates up to 6 guests and features air conditioning, internet, and a kitchen with a microwave and dishwasher, with nearby opportunities for kayaking, water skiing, and cycling.
9.9 134 reviews
Greensboro, MD
08/05 – 08/16
$136/nighttotal: $1496 (11 )
Cozy 2 Bedroom Home On Wooded Private Lane
1 4
apartment , Greensboro
This Greensboro rental, a tranquil Eastern Shore home on a quiet country lane, offers easy access to Easton, Dover, Chestertown, Rehoboth Beach, Denton, and Ocean City. The two-bedroom, two-bathroom house features a full kitchen with a fridge, freezer, microwave, and dishwasher; it accommodates four guests and includes a garden, air conditioning, internet access, and pet-friendly options (with prior permission and additional deposit).
10 9 reviews
Greensboro, MD
08/05 – 08/16
$185/nighttotal: $2035 (11 )
Welcome To Harmony House!
1 4
apartment , Denton
This Denton house rental, conveniently located near Highway 404, offers easy access to Denton's attractions. The three-bedroom, one-bathroom home sleeps four guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus high-speed Wi-Fi and parking.
Our Favorite Family-Friendly Vacation Rentals in Greensboro, MD
Make family travel to Greensboro, MD seamless with spacious vacation rentals located just minutes from top city attractions.
9.8 12 reviews
Greensboro, MD
08/05 – 08/16
$496/nighttotal: $5456 (11 )
Turnbridge Manor
5 4
apartment , Denton
This waterfront home is located in downtown Denton, Maryland's Eastern Shore, less than 60 minutes from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. It has earned excellent user ratings for its comfort and amenities. The apartment features 5 bedrooms and 3 bathrooms, comfortably accommodating up to 10 guests. It offers a blend of modern amenities and historic charm, including a garden, parking, internet access, and a fully equipped kitchen.
10 3 reviews
Greensboro, MD
08/05 – 08/16
$238/nighttotal: $2618 (11 )
Relaxation Haven On The Shore By Choptank River
1 4
gîte , Greensboro
This charming cottage in Greensboro, Eastern Shore, offers a tranquil setting amidst nature, despite being close to amenities. With excellent user, location, and cleanliness ratings, it has 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests. The apartment features a fully equipped kitchen, comfortable beds, a cozy living area, and outdoor garden areas for camping, a firepit altar, and meditation or Tai Chi. Guided meditation sessions are available upon request, adding to the apartment's wellness ambiance.
9.4 9 reviews
Greensboro, MD
08/05 – 08/16
$263/nighttotal: $2893 (11 )
Relaxation Haven On The Shore Near Choptank River
2 4
apartment , Greensboro
This Greensboro apartment rental is conveniently located near Tuckahoe State Park, Olive Branch Lodge Park, Adkins Arboretum, and Martinak State Park, all within a 6-10 mile radius. This two-bedroom, one-bathroom unit sleeps six guests and features a fully equipped kitchen, fireplace, washer/dryer, DVD player, and a balcony overlooking the on-site garden, offering easy access to area parks.
9.9 107 reviews
Greensboro, MD
08/05 – 08/16
$283/nighttotal: $3113 (11 )
Adorable 2-bedroom Bungalow Near Easton, Denton
1 4
house , Queen Anne
This charming Queen Anne 2-bedroom bungalow is situated in a quiet neighborhood near Easton, Denton, offering easy access to both urban amenities and natural attractions. Just a short drive from Killens Pond Water Park and within a reasonable driving distance of Sandy Point State Park and Chesapeake Exploration Center, this vacation rental boasts excellent user, location, and cleanliness ratings. The bungalow's inviting interior creates a warm and welcoming atmosphere, with a fully equipped kitchen, modern amenities, and a private outdoor space where guests can relax and enjoy the surrounding views. With a floor area of 140 square feet, the bungalow comfortably accommodates up to 4 guests, making it an ideal choice for families or small groups seeking a cozy and convenient vacation rental in Queen Anne.
Wigwam Lodge, a Goldsboro cabin rental near the Choptank River (5 minutes), Denton (20 minutes), and an hour from the beach, offers a convenient location with easy parking. This 1500-square-foot log home features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, jacuzzi, and fast Wi-Fi.
9.8 12 reviews
Greensboro, MD
08/05 – 08/16
$496/nighttotal: $5456 (11 )
Turnbridge Manor
5 4
apartment , Denton
This waterfront home is located in downtown Denton, Maryland's Eastern Shore, less than 60 minutes from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. It has earned excellent user ratings for its comfort and amenities. The apartment features 5 bedrooms and 3 bathrooms, comfortably accommodating up to 10 guests. It offers a blend of modern amenities and historic charm, including a garden, parking, internet access, and a fully equipped kitchen.
9.9 107 reviews
Greensboro, MD
08/05 – 08/16
$283/nighttotal: $3113 (11 )
Adorable 2-bedroom Bungalow Near Easton, Denton
1 4
house , Queen Anne
This charming Queen Anne 2-bedroom bungalow is situated in a quiet neighborhood near Easton, Denton, offering easy access to both urban amenities and natural attractions. Just a short drive from Killens Pond Water Park and within a reasonable driving distance of Sandy Point State Park and Chesapeake Exploration Center, this vacation rental boasts excellent user, location, and cleanliness ratings. The bungalow's inviting interior creates a warm and welcoming atmosphere, with a fully equipped kitchen, modern amenities, and a private outdoor space where guests can relax and enjoy the surrounding views. With a floor area of 140 square feet, the bungalow comfortably accommodates up to 4 guests, making it an ideal choice for families or small groups seeking a cozy and convenient vacation rental in Queen Anne.
9.9 134 reviews
Greensboro, MD
08/05 – 08/16
$136/nighttotal: $1496 (11 )
Cozy 2 Bedroom Home On Wooded Private Lane
1 4
apartment , Greensboro
This Greensboro rental, a tranquil Eastern Shore home on a quiet country lane, offers easy access to Easton, Dover, Chestertown, Rehoboth Beach, Denton, and Ocean City. The two-bedroom, two-bathroom house features a full kitchen with a fridge, freezer, microwave, and dishwasher; it accommodates four guests and includes a garden, air conditioning, internet access, and pet-friendly options (with prior permission and additional deposit).
Frequently Asked Questions about vacation rentals in Greensboro, MD
What other towns or cities can be easily accessed from Greensboro, MD?
Greensboro is located on Maryland's Eastern Shore, so you can easily access other towns and cities in the area. You can drive to Cambridge, MD, in about 20 minutes, or to Easton, MD, in about 45 minutes. If you want to visit Baltimore, MD, it's about a two-hour drive.
What are the best Airbnb and vacation rentals in Greensboro, MD?
What amenities are commonly available in vacation rentals in Greensboro, MD?
Vacation rentals in Greensboro usually offer a range of amenities, including kitchens, laundry facilities, and outdoor spaces. Many rentals also have Wi-Fi, cable TV, and air conditioning. Some rentals may even have private docks or swimming pools.
What are the most popular Airbnbs in Greensboro, MD?
What time of year is best to rent a vacation rental Greensboro, MD?
The best time to visit Greensboro depends on your interests. If you want to enjoy the warm weather and go swimming, boating, or fishing, then summer is the best time to visit. If you prefer cooler weather and want to see the fall foliage, then autumn is a good option. Spring is also a nice time to visit, as the weather is mild and the flowers are in bloom.
What are the best rentals for families and kids in Greensboro, MD?
What are the local dishes in Greensboro, MD region?
The Eastern Shore is known for its seafood, so you'll find plenty of crab cakes, oysters, and fish on the menus in Greensboro. You can also find other local specialties, such as Eastern Shore chicken, which is a type of fried chicken. If you're looking for something sweet, try a Smith Island cake, a layered cake with a rich chocolate frosting.
What are the best rentals or Airbnbs with a jacuzzi in Greensboro, MD?
Find the Best Vacation Rentals with Balconies in Greensboro, MD
Enjoy stunning views from your private terrace when you book one of these vacation rentals in Greensboro, MD.
9.9 107 reviews
Greensboro, MD
08/05 – 08/16
$283/nighttotal: $3113 (11 )
Adorable 2-bedroom Bungalow Near Easton, Denton
1 4
house , Queen Anne
This charming Queen Anne 2-bedroom bungalow is situated in a quiet neighborhood near Easton, Denton, offering easy access to both urban amenities and natural attractions. Just a short drive from Killens Pond Water Park and within a reasonable driving distance of Sandy Point State Park and Chesapeake Exploration Center, this vacation rental boasts excellent user, location, and cleanliness ratings. The bungalow's inviting interior creates a warm and welcoming atmosphere, with a fully equipped kitchen, modern amenities, and a private outdoor space where guests can relax and enjoy the surrounding views. With a floor area of 140 square feet, the bungalow comfortably accommodates up to 4 guests, making it an ideal choice for families or small groups seeking a cozy and convenient vacation rental in Queen Anne.
9.4 9 reviews
Greensboro, MD
08/05 – 08/16
$263/nighttotal: $2893 (11 )
Relaxation Haven On The Shore Near Choptank River
2 4
apartment , Greensboro
This Greensboro apartment rental is conveniently located near Tuckahoe State Park, Olive Branch Lodge Park, Adkins Arboretum, and Martinak State Park, all within a 6-10 mile radius. This two-bedroom, one-bathroom unit sleeps six guests and features a fully equipped kitchen, fireplace, washer/dryer, DVD player, and a balcony overlooking the on-site garden, offering easy access to area parks.
Top Dog-Friendly Vacation Rentals in Greensboro, MD
Travel with ease to Greensboro, MD with pet-friendly rentals located near local dog parks and scenic city walks.
9.9 134 reviews
Greensboro, MD
08/05 – 08/16
$136/nighttotal: $1496 (11 )
Cozy 2 Bedroom Home On Wooded Private Lane
1 4
apartment , Greensboro
This Greensboro rental, a tranquil Eastern Shore home on a quiet country lane, offers easy access to Easton, Dover, Chestertown, Rehoboth Beach, Denton, and Ocean City. The two-bedroom, two-bathroom house features a full kitchen with a fridge, freezer, microwave, and dishwasher; it accommodates four guests and includes a garden, air conditioning, internet access, and pet-friendly options (with prior permission and additional deposit).
9.9 98 reviews
Greensboro, MD
08/05 – 08/16
$356/nighttotal: $3916 (11 )
Turnbridge Manor - Waterfront Historic House
5 4
apartment , Denton
This waterfront rental is located in downtown Denton, Maryland's Eastern Shore, less than an hour from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. This apartment has received excellent ratings for cleanliness, location, and user experience. This five-bedroom, three-bathroom home can accommodate up to 10 guests. The apartment offers a blend of modern amenities and historic charm, with features like gas fireplaces, multiple outdoor spaces, and a kitchen with a separate entrance.
9.8 12 reviews
Greensboro, MD
08/05 – 08/16
$496/nighttotal: $5456 (11 )
Turnbridge Manor
5 4
apartment , Denton
This waterfront home is located in downtown Denton, Maryland's Eastern Shore, less than 60 minutes from the beach, 35 minutes from historic St. Michaels, and minutes from the Harriet Tubman Byway. It has earned excellent user ratings for its comfort and amenities. The apartment features 5 bedrooms and 3 bathrooms, comfortably accommodating up to 10 guests. It offers a blend of modern amenities and historic charm, including a garden, parking, internet access, and a fully equipped kitchen.
10 9 reviews
Greensboro, MD
08/05 – 08/16
$185/nighttotal: $2035 (11 )
Welcome To Harmony House!
1 4
apartment , Denton
This Denton house rental, conveniently located near Highway 404, offers easy access to Denton's attractions. The three-bedroom, one-bathroom home sleeps four guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus high-speed Wi-Fi and parking.