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Greensboro Holiday Rentals

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Our top choices for Greensboro holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (122 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is NZ$268
includes taxes & fees
24 Aug - 25 Aug
First Floor Studio Apartment in Historic Chestertown

2. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is NZ$210
includes taxes & fees
15 Sept - 16 Sept
Guest Suite for up to 2 in a Victorian on the Chester River

3. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is NZ$343
includes taxes & fees
21 Sept - 22 Sept
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

4. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is NZ$294
includes taxes & fees
20 Sept - 21 Sept
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

5. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is NZ$162
includes taxes & fees
26 Aug - 27 Aug
Cozy Room in Dover

6. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,020
includes taxes & fees
27 Aug - 28 Aug
Turnbridge Manor

7. Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! "
United States
Shaine L.
The price is NZ$369
includes taxes & fees
2 Sept - 3 Sept
Cozy Unit in Milford, Delaware -Close to DE Turf

8. Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our family while at a lacrosse tournament. It was close to the field and very comfortable. Having two full bathrooms to get ready for the day was a treat! The property was clean and spacious. Also, the host was also extremely responsive. We will definitely return."
United States
Jill M.
The price is NZ$637
includes taxes & fees
2 Sept - 3 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is NZ$690
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor

10. Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
10.0 out of 10, Exceptional, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is NZ$509
includes taxes & fees
23 Aug - 24 Aug
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

11. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"We had an absolutely wonderful stay at this adorable glamping camper oasis while in town for the NASCAR All-Star Race weekend. The camper and property were spotless, beautifully maintained, and it has so many thoughtful amenities that made our stay comfortable and relaxing.The heated pool was amazing after a long day, and the entire atmosphere was peaceful, welcoming, and fun. The hosts were incredibly friendly, gracious, and accommodating throughout our stay. You can truly tell they take...
United States
Roberta J.
The price is NZ$405
includes taxes & fees
6 Sept - 7 Sept
Mini Aruba RV/Glamping Tent

12. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
8.6 out of 10, Excellent, (15 reviews)
"Theme decor was awesome. Location was a quick stroll downtown. Very busy street so use a white noise app on your phone if street noise is an issue."
United States
Dee Z. B.
The price is NZ$463
includes taxes & fees
25 Aug - 26 Aug
Poe Themed Home Close to Beaches and DE Turf

13. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is NZ$706
includes taxes & fees
28 Aug - 29 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

14. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is NZ$471
includes taxes & fees
23 Aug - 24 Aug
Secluded Cottage in Middle of Chestertown

15. Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Milford
8.8 out of 10, Excellent, (6 reviews)
The price is NZ$464
includes taxes & fees
25 Aug - 26 Aug
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

16. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is NZ$576
includes taxes & fees
30 Aug - 31 Aug
Newly restored apartment in the heart of Chestertown

17. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is NZ$806
includes taxes & fees
1 Sept - 2 Sept
Wren Retweet- Country Estate in Center of C’Town
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.
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Top Greensboro Hotel Reviews

Find out more about Greensboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greensboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greensboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Greensboro. Seeing all the best attractions is bound to make you fall in love with Greensboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Greensboro short-term rentals, that won’t be hard to do.

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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This highly rated holiday home rental in Greensboro is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Abbott's Mill Nature Center. In the wider area, you’ll find Tuckahoe State Park and Harrington Raceway and Casino.

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.