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Greensboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Greensboro vacation 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)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Sep 30 - Oct 1
Total with taxes and fees
Turnbridge Manor
A bedroom with a bunk bed, a single bed, a desk, and a chair.

2. 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.
$170 nightly
The price is $172
Sep 30 - Oct 1
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

3. 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, (28 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.
$118 nightly
The price is $125
Sep 30 - Oct 1
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
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.
$260 nightly
The price is $287
Sep 30 - Oct 1
Total with taxes and fees
Family Retreat at Lansdowne Manor
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

5. 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, (11 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$181 nightly
The price is $186
Oct 6 - Oct 7
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (127 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
$144 nightly
The price is $159
Oct 1 - Oct 2
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A modern living space with a dining area, sofa, and kitchen.

7. 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.
$305 nightly
The price is $325
Sep 30 - Oct 1
Total with taxes and fees
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

8. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
$248 nightly
The price is $255
Oct 12 - Oct 13
Total with taxes and fees
Mini Aruba RV/Glamping Tent
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

9. 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.
$219 nightly
The price is $224
Sep 30 - Oct 1
Total with taxes and fees
Cozy Unit in Milford, Delaware -Close to DE Turf
A patio area with outdoor seating, string lights, and potted plants.

10. 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, (16 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.
$268 nightly
The price is $275
Sep 30 - Oct 1
Total with taxes and fees
Poe Themed Home Close to Beaches and DE Turf
A wooden cabin with a porch, a rocking chair, and a table.

11. 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.
$301 nightly
The price is $310
Sep 30 - Oct 1
Total with taxes and fees
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

12. 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.
$264 nightly
The price is $274
Sep 30 - Oct 1
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

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
$508 nightly
The price is $538
Sep 30 - Oct 1
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A modern kitchen with a large island, bar stools, and pendant lighting.

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

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
$662 nightly
The price is $673
Sep 30 - Oct 1
Total with taxes and fees
Spacious 5 Bedroom w/Pool, Patio and Theater
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

15. 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.
$501 nightly
The price is $512
Sep 30 - Oct 1
Total with taxes and fees
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A deck with outdoor furniture, a potted plant, and a house in the background.

16. 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.
$290 nightly
The price is $307
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A spacious living area with a dining table, sofa, and a kitchen in the background.

17. 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)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$302 nightly
The price is $334
Oct 5 - Oct 6
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
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.
$463 nightly
The price is $481
Oct 6 - Oct 7
Total with taxes and fees
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
$732 nightly
The price is $732
Sep 30 - Oct 1
Total with taxes and fees
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
$711 nightly
The price is $728
Sep 30 - Oct 1
Total with taxes and fees
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"I only interacted with front desk staff at check-in and check out they were very pleasant. The hotel itself was just ok. Lobby was beautiful, but the rooms are dated. Just ok for a night."
Frances 1-night trip
Posted 8 hours ago
Bally's Dover Casino Resort

Find out more about Greensboro

Everything you need to know about Greensboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greensboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greensboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Greensboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greensboro rentals

At Expedia, we put the best Greensboro vacation 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 vacation.

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 vacation rentals in Greensboro?

Yes, we offer vacation rentals near the most popular points of interest in Greensboro, or you can select a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in Greensboro. Make sure you have time to check out the waterfront and coffeehouses during your trip.

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

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This Greensboro vacation home rental is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can immerse yourself in your vacation.

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 larger area, you’ll find Tuckahoe State Park and Martinak State Park.

What are vacation rentals like in Greensboro?

Vacation rentals are private accommodations you can stay in for a short or long stay in Greensboro. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.