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Top Holiday Rentals in Greensboro

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (90)
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
-A travelers cottage - A place to rest after a busy day.
TV
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, (18)
"My husband, son and myself stayed for 7 nights. Walk in shower lower level worked great. Theres also a full bath upstairs. Location was quiet, but not too far from food stores and restaurants."
-A travelers cottage - A place to rest after a busy day.
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Property grounds
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
10.0 out of 10, Exceptional, (3)
"Beautiful location. Very quiet and relaxing."
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
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Guest suite in the woods with private entry
Exterior
Guest suite in the woods with private entry
10.0 out of 10, Exceptional, (35)
"This is a really lovely property located about 15 miles south of the Delaware turf. It was quiet, clean and very comfortable. There were two queen size beds to sleep in nice size, bathroom, coffee, service in the room, as well as a decent size refrigerator, and a microwave. it is a family home there are, some comfort noises like children foot but overall, I really liked staying here and having the opportunity to get away from the typical hotel environment."
Guest suite in the woods with private entry
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (53)
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (60)
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is £133
per night
17 Jun - 18 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, (4)
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Grandma's Cottage
Exterior
Grandma's Cottage
10.0 out of 10, Exceptional, (79)
"We had a wonderful long weekend stay at Grandma's Cottage. We had traveled from Lancaster County, Pa in an antique vehicle for a car show at the Dover Speedway. Although our daily commute was aprox 25 minutes, it was worth the drive to the Cottage. We spent our evenings at the Dining table eating, playing games and enjoying the view of the Lake. The stillness of the property and the ducks floating up and down the Lake reminded us to just be still and enjoy peace and quiet from our normal...
Grandma's Cottage
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
Interior
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
10.0 out of 10, Exceptional, (13)
"Was looking for spot while son was at DE Turf for weekend lacrosse tournament . This quaint spot was perfect for our stay. 25min to DETurf , 15min to restaurants , and the quiet comfort was great! Hopefully available in Oct !!!"
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Fridge, microwave, oven, stovetop
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
Property grounds
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
10.0 out of 10, Exceptional, (11)
"Location was great for what we had planned. Clean and well cared for. Great communication with the host. Would stay again!"
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
Private pier and pool at this waterfront Chestertown home
Aerial view
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, (22)
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Gorgeous Creek Side Ranch-Style Estate With Dock
Fridge, microwave, oven, stovetop
Gorgeous Creek Side Ranch-Style Estate With Dock
9.0 out of 10, Wonderful, (2)
"Beautiful, comfortable house on huge creek front lot. Even better than the pictures! Communication was very easy, we loved the yard and landscaping. Great bird watching from the deck or through the huge picture windows. Highly recommend!"
The price is £610
per night
20 Jun - 21 Jun
Gorgeous Creek Side Ranch-Style Estate With Dock
Grasonville Home w/ Private Pool on the Water
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (14)
"We had a wonderful time in Grasonville. The property was very clean and well maintained. Views from the home were serene as most rooms have views of the water which we absolutely loved. Another perk of the home is its proximity to surrounding attractions. Our group felt like we were secluded enough but could easily get something in town if needed. We didn’t need much since the home was well stocked. When we contacted the host about a question, they responded quickly. We would definitely stay...
Grasonville Home w/ Private Pool on the Water
Home away from home
Interior
Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Stylish Home on the Choptank River (with Tidal Beach)
Property grounds
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, (25)
"The home is clean, comfortable, and has a gorgeous outdoor living space right on the water. We even had my son's wedding day party prep photos taken here. We would definitely stay here again."
Stylish Home on the Choptank River (with Tidal Beach)
Blue Room in Delaware
1 bedroom, iron/ironing board, Internet
Blue Room in Delaware
8.0 out of 10, Very good, (1)
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (77)
"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Don't see what you're looking for?
See all available properties in Greensboro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Greensboro Holiday Rental Travel Info

Popular accommodation
Greensboro apartments
Known landmarks
Tuckahoe State Park, Martinak State Park and Museum of Rural Life
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Greensboro you may be interested in

Bally's Dover Casino Resort
Front of property
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1391)
"I liked the Price."
The price is £74
per night
1 Jul - 2 Jul
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
Exterior
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, (1004)
"Excellent staff and clean room, wish it had ice machine but everything was great!"
The price is £77
per night
17 Jun - 18 Jun
Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, (1004)
"This was a very clean and comfortable place to stay. Extra bonus that they do not charge for pets. Staff was friendly and helpful. I would definitely recommend this place "
The price is £70
per night
17 Jun - 18 Jun
Red Roof Inn & Suites Dover Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Greensboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greensboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greensboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greensboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greensboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greensboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greensboro holiday rentals we have selected for you start as low as £133 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greensboro rentals

At Expedia, we put the best Greensboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greensboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greensboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greensboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Greensboro?

Yes, there are holiday rentals close to the most popular sights in Greensboro, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in Greensboro. Make sure you have time to check out the waterfront and coffee shops during your trip.

What are some of the best holiday rentals that Greensboro has to offer?

Hidden gem with water and golf course views! Bike ride to downtown!: This holiday home rental outside Greensboro is located next to a golf course, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and 1 hot tub.

What can I see and do in Greensboro?

Explore the area and family-friendly sights such as Delaware State Fairgrounds, or get out into nature at a spot like Tuckahoe State Park. In the wider area, you’ll find Harrington Raceway and Casino and Killens Pond State Park.

What are holiday rentals like in Greensboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greensboro. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.

Recent reviews of Greensboro properties
Expedia verified reviews

Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

5/5 Excellent
"Excellent staff and clean room, wish it had ice machine but everything was great!"
A verified traveller stayed at Microtel Inn & Suites by Wyndham Dover
Posted 18 hours ago
Microtel Inn & Suites by Wyndham Dover