Greensboro Vacation Rentals

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Vacation Rentals in Greensboro

Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, 18 reviews
"My husband, son and myself stayed for 7 nights. Walk in shower lower level worked great. Theres also a full bath upstairs. Location was quiet, but not too far from food stores and restaurants."
-A travelers cottage - A place to rest after a busy day.
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
10.0 out of 10, Exceptional, 3 reviews
"Beautiful location. Very quiet and relaxing."
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Guest suite in the woods with private entry
10.0 out of 10, Exceptional, 35 reviews
"I would highly recommend a stay in their home. They were awesome when it came to communicating with us when then app was having issues. Very quiet location, we all got a great nights sleep. It was very convenient for us while we were in town for a tournament at the DE Turf Complex, about a twenty minute ride. "
Guest suite in the woods with private entry
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 53 reviews
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is CA $151
CA $225 total
includes taxes & fees
Jul 3 - Jul 4
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, 4 reviews
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Grandma's Cottage
10.0 out of 10, Exceptional, 80 reviews
"Grandma’s Cottage was exactly what we needed ! It was very quiet, with many nice hiking trails, fishing spots, stores & restaurants just a short drive away. The cottage was so clean & comfortable, with a beautiful lake setting. Everything we needed and more was provided. Helen & TJ were great hosts & take great pride in maintaining Grandma’s Cottage. They were very friendly & right next door if we needed anything…yet gave us our privacy. We’ve already booked a return trip. You won’t be...
Grandma's Cottage
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, 1 review
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
10.0 out of 10, Exceptional, 13 reviews
"Was looking for spot while son was at DE Turf for weekend lacrosse tournament . This quaint spot was perfect for our stay. 25min to DETurf , 15min to restaurants , and the quiet comfort was great! Hopefully available in Oct !!!"
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, 3 reviews
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
The price is CA $1,198
CA $3,007 total
includes taxes & fees
Jul 18 - Jul 19
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 3 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
10.0 out of 10, Exceptional, 11 reviews
"Location was great for what we had planned. Clean and well cared for. Great communication with the host. Would stay again!"
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, 22 reviews
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Gorgeous Creek Side Ranch-Style Estate With Dock
9.4 out of 10, Exceptional, 3 reviews
"This house is perfect for family gatherings! The backyard is wonderful with a beautiful dock and beautiful landscaping. We ate all our meals out on the deck. The house was very clean and very accommodating."
The price is CA $279
CA $1,055 total
includes taxes & fees
Jun 23 - Jun 24
Gorgeous Creek Side Ranch-Style Estate With Dock
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, 14 reviews
"We had a wonderful time in Grasonville. The property was very clean and well maintained. Views from the home were serene as most rooms have views of the water which we absolutely loved. Another perk of the home is its proximity to surrounding attractions. Our group felt like we were secluded enough but could easily get something in town if needed. We didn’t need much since the home was well stocked. When we contacted the host about a question, they responded quickly. We would definitely stay...
Grasonville Home w/ Private Pool on the Water
Home away from home
7.6 out of 10, Good, 5 reviews
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, 25 reviews
"The home is clean, comfortable, and has a gorgeous outdoor living space right on the water. We even had my son's wedding day party prep photos taken here. We would definitely stay here again."
Stylish Home on the Choptank River (with Tidal Beach)
Blue Room in Delaware
8.0 out of 10, Very good, 1 review
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, 78 reviews
"Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Don't see what you're looking for?
See all available properties in Greensboro
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.

Greensboro Vacation Rental Travel Info

Other types of properties in Greensboro you may be interested in

Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,407 reviews
"Harry goes beyond his way to help with guests. The staff is extremely friendly and helpful. The hotel could use an upgrade. "
The price is CA $92
CA $123 total
includes taxes & fees
Jul 1 - Jul 2
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, 1,003 reviews
"It was a good place to stay for a couple of nights. "
The price is CA $122
CA $134 total
includes taxes & fees
Jun 24 - Jun 25
Microtel Inn & Suites by Wyndham Dover
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, 1,004 reviews
" the customer service was great for me checking in and far as advice on where to get something to eat and far as showing me where the casino was I like the professionalism that they show"
The price is CA $111
CA $121 total
includes taxes & fees
Jun 25 - Jun 26
Red Roof Inn & Suites Dover Downtown
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.

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?

Hidden gem with water and golf course views! Bike ride to downtown!: You might like this vacation home rental near Greensboro. It is located next to a golf course and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and a spa tub.

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 Tuckahoe State Park. In the larger area, you’ll find Harrington Raceway and Casino and Killens Pond 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.

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