Greensboro Holiday Rentals

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Holiday Rentals in Greensboro

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (59)
"We had a fantastic time- the location on the water was gorgeous and loved the hot tub and pool. Extremely quiet and private!"
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Grandma's Cottage

10.0 out of 10, Exceptional, (103)
"5 nights in grandsma cottage and we enjoy every things..."
Grandma's Cottage

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (228)
"Awesome place. "
Cozy cottage on the Miller farm.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (102)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (2)
"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "
The price is NZ$450
includes taxes & fees
18 Aug - 19 Aug
Poe Themed Home Close to Beaches and DE Turf

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"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!"
The price is NZ$377
includes taxes & fees
3 Aug - 4 Aug
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is NZ$263
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (88)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (8)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is NZ$738
includes taxes & fees
28 July - 29 July
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (8)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.8 out of 10, Exceptional, (18)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

9.8 out of 10, Exceptional, (9)
"We loved our stay! "
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

Peaceful living just outside of town

9.8 out of 10, Exceptional, (7)
"We really enjoyed our time there! The children enjoyed the playground set. We truly recommend! We are so grateful. Thank you! "
Peaceful living just outside of town

On-Site Boat Dock: Queenstown Home w/ Pool & Yard!

On-Site Boat Dock: Queenstown Home w/ Pool & Yard!

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is NZ$1,486
includes taxes & fees
3 Aug - 4 Aug
Gorgeous Creek Side Ranch-Style Estate With Dock
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

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?

Cozy cottage on the Miller farm. : This holiday home rental outside of Greensboro offers a private garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Abbott's Mill Nature Center. 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.