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Greensboro Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Greensboro holiday rentals

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is HK$2,825
HK$4,783 total
includes taxes & fees
29 Oct - 30 Oct
Turnbridge Manor
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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, (29 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 HK$534
HK$982 total
includes taxes & fees
19 Oct - 20 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is HK$777
HK$1,247 total
includes taxes & fees
19 Oct - 20 Oct
First Floor Studio Apartment in Historic Chestertown
A kitchen with wooden cabinets, a dining table, and a refrigerator.

4. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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.
Family Retreat at Lansdowne Manor
A bedroom with a bunk bed, a single bed, a desk, and a chair.

5. 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 HK$706
HK$1,672 total
includes taxes & fees
4 Nov - 5 Nov
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

6. 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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is HK$746
HK$1,250 total
includes taxes & fees
22 Oct - 23 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

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

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
9.6 out of 10, Exceptional, (4 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 HK$932
HK$1,759 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Unit in Milford, Delaware -Close to DE Turf
A modern living space with a dining area, sofa, and kitchen.

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 HK$613
HK$2,660 total
includes taxes & fees
19 Oct - 20 Oct
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A patio area with outdoor seating, string lights, and potted plants.

9. 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, (17 reviews)
"The owner thought of many amenities that I haven't seen before like breakfast bars and oatmeal packets. Very much appreciated."
United States
Sharon
The price is HK$1,271
HK$2,160 total
includes taxes & fees
17 Oct - 18 Oct
Poe Themed Home Close to Beaches and DE Turf
A wooden cabin with a porch, a rocking chair, and a table.

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, (2 reviews)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is HK$1,491
HK$2,429 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A modern kitchen with a large island, bar stools, and pendant lighting.

11. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
Spacious 5 Bedroom w/Pool, Patio and Theater
A deck with outdoor furniture, a potted plant, and a house in the background.

12. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is HK$1,727
HK$2,429 total
includes taxes & fees
22 Oct - 23 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

13. 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 HK$1,441
HK$2,150 total
includes taxes & fees
26 Oct - 27 Oct
Secluded Cottage in Middle of Chestertown
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

14. 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
9.4 out of 10, Exceptional, (12 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
The price is HK$1,583
HK$2,557 total
includes taxes & fees
19 Oct - 20 Oct
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A spacious living area with a dining table, sofa, and a kitchen in the background.

15. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is HK$1,766
HK$2,764 total
includes taxes & fees
18 Oct - 19 Oct
Newly restored apartment in the heart of Chestertown
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

16. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
Welcome to the secluded waterfront oasis
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

17. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
The price is HK$1,876
HK$4,291 total
includes taxes & fees
18 Oct - 19 Oct
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A hallway with wooden flooring, a door on the right, and a window at the end.

18. 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 HK$2,390
HK$3,777 total
includes taxes & fees
27 Oct - 28 Oct
Wren Retweet- Country Estate in Center of C’Town
A patio with a table and chairs, an umbrella, and a covered grill.

19. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
The price is HK$3,296
HK$5,744 total
includes taxes & fees
19 Oct - 20 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
A balcony with a view of a grassy field, a white fence, and a building with a grey roof.

20. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
The price is HK$2,755
HK$5,713 total
includes taxes & fees
18 Oct - 19 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
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

Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

10/10 Excellent
"Very clean staff always friendly. Didn't eat breakfast this time but very limited"
Phyllis 1-night trip
Posted 2 hours ago
Microtel Inn & Suites by Wyndham Dover

Find out more about Greensboro

Search for holiday rentals in Greensboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Greensboro using one of the methods below:

  • View our selection of featured holiday rentals in Greensboro
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  • Enter your travel dates to view the best deals on holiday rentals in Greensboro while they last

Look no further and take a look at our great range of rental properties in Greensboro!

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 Saulsbury Road Park. In the wider area, you’ll find Tuckahoe State Park and Martinak 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.