Greensboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Greensboro vacation rentals

A two-story house with a porch, two windows, and a door.

1. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is CA $318
CA $496 total
includes taxes & fees
Dec 1 - Dec 2
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $95
CA $163 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
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.

3. 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 CA $505
CA $823 total
includes taxes & fees
Nov 9 - Nov 10
Turnbridge Manor
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $133
CA $212 total
includes taxes & fees
Nov 29 - Nov 30
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.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $139
CA $211 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A modern living space with a dining area, sofa, and kitchen.

6. 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 CA $93
CA $418 total
includes taxes & fees
Nov 8 - Nov 9
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A bedroom with a bunk bed, a single bed, a desk, and a chair.

7. 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 CA $165
CA $345 total
includes taxes & fees
Nov 10 - Nov 11
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

8. 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 CA $167
CA $302 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Unit in Milford, Delaware -Close to DE Turf
A kitchen with wooden cabinets, a dining table, and a refrigerator.

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 CA $322
CA $377 total
includes taxes & fees
Nov 10 - Nov 11
Family Retreat at Lansdowne Manor
A single-story house with a garage, a front lawn, and a driveway.

10. A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford

A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford
Milford
The price is CA $210
CA $402 total
includes taxes & fees
Nov 9 - Nov 10
A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford
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.
The price is CA $266
CA $413 total
includes taxes & fees
Nov 29 - Nov 30
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A patio area with outdoor seating, string lights, and potted plants.

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, (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 CA $229
CA $358 total
includes taxes & fees
Nov 8 - Nov 9
Poe Themed Home Close to Beaches and DE Turf
A garden path leading to a wooden building with a rustic appearance.

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 CA $257
CA $368 total
includes taxes & fees
Nov 8 - Nov 9
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, (13 reviews)
"Great experience! I had a few questions, and the owners responded within MINUTES!"
United States
Jenn K.
The price is CA $251
CA $396 total
includes taxes & fees
Nov 9 - Nov 10
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

15. 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 CA $278
CA $389 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Living area

16. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is CA $315
CA $565 total
includes taxes & fees
Nov 11 - Nov 12
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A modern kitchen with a large island, bar stools, and pendant lighting.

17. 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.
The price is CA $432
CA $990 total
includes taxes & fees
Nov 30 - Dec 1
Spacious 5 Bedroom w/Pool, Patio and Theater
A spacious living area with a dining table, sofa, and a kitchen in the background.

18. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 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 CA $315
CA $451 total
includes taxes & fees
Nov 8 - Nov 9
Newly restored apartment in the heart of Chestertown
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

19. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $378
CA $437 total
includes taxes & fees
Nov 10 - Nov 11
Family Friendly Cozy 3 Bedroom Duplex
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

20. 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, (5 reviews)
"Host was great"
United States
mark o.
The price is CA $338
CA $842 total
includes taxes & fees
Nov 20 - Nov 21
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
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

A spacious lobby with a central fountain, marble flooring, and columns with greenery.
Bally's Dover Casino Resort

Bally's Dover Casino Resort

Bally's Dover Casino Resort
Dover

10/10 Excellent

The staff are extremely helpful and informative and friendly.
Canada
Howard
Reviewed August 31, 2026
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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greensboro vacation rentals we have selected for you start as low as CA $93 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 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.