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Greensboro Vacation Rentals

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Our top choices for Greensboro vacation rentals

1. 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 CA $558
CA $921 total
includes taxes & fees
Aug 27 - Aug 28
Turnbridge Manor

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, (26 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 CA $95
CA $174 total
includes taxes & fees
Sep 10 - Sep 11
Guest Suite for up to 2 in a Victorian on the Chester River

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $138
CA $221 total
includes taxes & fees
Aug 12 - Aug 13
First Floor Studio Apartment in Historic Chestertown

4. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is CA $82
CA $134 total
includes taxes & fees
Aug 15 - Aug 16
Cozy Room in Dover

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
9.8 out of 10, Exceptional, (10 reviews)
"The pictures were accurate. Our host communicated with us in a timely manner. Everything was as it said it was going to be everything in the house worked and made sense. We really enjoyed our stay. We definitely will be staying at this location again when we come in into Dover."
United States
Laura
The price is CA $138
CA $228 total
includes taxes & fees
Sep 10 - Sep 11
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

6. 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 $112
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

7. 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 CA $477
CA $599 total
includes taxes & fees
Sep 8 - Sep 9
Family Retreat at Lansdowne Manor

8. 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 CA $314
CA $488 total
includes taxes & fees
Aug 20 - Aug 21
Newly restored apartment in the heart of Chestertown

9. 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, (15 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 CA $348
CA $588 total
includes taxes & fees
Aug 13 - Aug 14
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

10. Milford Quiet Coastal Retreat 3br Sleeps 8 3 Bedroom Home

Milford Quiet Coastal Retreat 3br Sleeps 8 3 Bedroom Home
3.0 star property
Milford
The price is CA $357
CA $893 total
includes taxes & fees
Sep 2 - Sep 3
Milford Quiet Coastal Retreat 3br Sleeps 8 3 Bedroom Home

11. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is CA $201
CA $330 total
includes taxes & fees
Sep 9 - Sep 10
Mini Aruba RV/Glamping Tent

12. 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 $173
CA $542 total
includes taxes & fees
Sep 9 - Sep 10
Luxury 2 bedroom Apt. Near DE Turf & Beaches!

13. 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 CA $238
CA $397 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

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 CA $256
CA $391 total
includes taxes & fees
Aug 24 - Aug 25
Secluded Cottage in Middle of Chestertown

15. 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 CA $447
CA $681 total
includes taxes & fees
Sep 9 - Sep 10
Wren Retweet- Country Estate in Center of C’Town

16. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
9.0 out of 10, Wonderful, (14 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 CA $226
CA $385 total
includes taxes & fees
Aug 12 - Aug 13
Poe Themed Home Close to Beaches and DE Turf

17. 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 CA $295
CA $424 total
includes taxes & fees
Aug 24 - Aug 25
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

18. 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)
"The unit is tiny but knowing we wouldn’t be spending much time there, it was fine for our use. I liked that we could walk to locations in town. Her directions for use were very clear and precise."
United States
Rebecca N.
The price is CA $175
CA $322 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Unit in Milford, Delaware -Close to DE Turf
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.