Greensboro Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Greensboro

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
10.0 out of 10, Exceptional, (5)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AU$531
includes taxes & fees
30 Sept - 1 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is AU$222
includes taxes & fees
9 Oct - 10 Oct
First Floor Studio Apartment in Historic Chestertown
Grandma's Cottage
10.0 out of 10, Exceptional, (92)
"Beautifully furnished cozy cottage by the Lake! This is my family’s home away from home!! "
Grandma's Cottage
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"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
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (60)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (16)
"We had a great stay! Scott was a fabulous host and answered all of our questions. The location was perfect and the home was well equipped for all of our needs. Will definitely be back!"
Grasonville Home w/ Private Pool on the Water
Blake House Historic Estate with Private Inn
10.0 out of 10, Exceptional, (17)
"We had such an amazing 5 nights at Blake House. Such a beautiful historic home and incredible setting sitting on a lovely bluff overlooking the Corsica River. We loved the beautiful pool- which was surrounded by the most colorful hydrangeas. We kayaked and saw many osprey, herons, and a bald eagle that fit our 4th of July get together! The beds were very comfortable, the kitchen gorgeous and well stocked - the fire pit on the bluff a perfect spot to enjoy the stars at night. We had a one mile...
Blake House Historic Estate with Private Inn
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (96)
"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
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Waterfront family resort Lodge with private pier, game room and bar
9.8 out of 10, Exceptional, (21)
"We stayed at this property over Labor Day weekend. The house and location are truly special. My group would love to stay here again!"
Waterfront family resort Lodge with private pier, game room and bar
Hidden gem with water and golf course views! Bike ride to downtown!
10.0 out of 10, Exceptional, (29)
"We had a wonderful time! The house was described perfectly. It was clean and comfortable and everything we needed it to be to enjoy our time! "
Hidden gem with water and golf course views! Bike ride to downtown!
Guest suite in the woods with private entry
10.0 out of 10, Exceptional, (38)
"Rather than staying at a noisy hotel, we opted to go with the VRBO while at a lax tourney at the DE turf. The house is located in a quiet area. We ventured into surrounding towns for local restaurants and shopping. (It does take 12-15 min to get anywhere). The accommodations were comfortable and my daughter and I had our own sleeping areas. "
Guest suite in the woods with private entry
Guest Suite for up to 2 in a Victorian on the Chester River
10.0 out of 10, Exceptional, (7)
"Cozy, charming, lovely, many other descriptive words like that. Well kept laid back tiny community. The host was great super nice and helpful. Would totally recommend! "
The price is AU$184
includes taxes & fees
1 Oct - 2 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, (12)
"Everything about our stay was delightful. Not even tropical storm Debby could put a damper on our stay and visit with family in Chestertown. The property is remarkable and the setting incomparable. Stunning sunsets on the Chester River were equaled by the comfort and style of Harbor View Haven."
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
9.6 out of 10, Exceptional, (24)
"It was great!"
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
10.0 out of 10, Exceptional, (24)
"This cozy cabin was a great retreat for my husband and myself. We really enjoyed our stay!"
Cozy tiny cabin with sunrise view! Short drive to beaches and turf.
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
10.0 out of 10, Exceptional, (7)
" Wonderful quiet property with a fully equipped stay. AC, Lighting, bug prevention, kitchen amenities, and linens were huge positives. The water temp/controls were a tad confusing and variable, difficult to tell the cause. Another comfort note would be the ladder rungs to the upper bed - they were extremely difficult and uncomfortable to use. There isn't much room for a ladder, so the selected style is understandable, but for anyone looking for a quick and easy sleeping sleeping arrangement...
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (62)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (22)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.8 out of 10, Exceptional, (7)
"This was a much needed weekend away and we hit the jackpot! Communication with our host was excellent and so accommodating. We searched for a place where we could relax and have fun, and this rental checked all the boxes. Beautifully decorated, picturesque setting, with all the special touches. I would rent this home again and work with this host for any other properties. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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.
Save an average of 15% on thousands of hotels when you're signed in

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, (1742)
"It was hard to find a place to park. Limited parking for handicap. "
The price is AU$136
includes taxes & fees
14 Oct - 15 Oct
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, (1001)
"O"
The price is AU$134
includes taxes & fees
6 Oct - 7 Oct
Microtel Inn & Suites by Wyndham Dover
Comfort Inn & Suites
2.5 star property
8.8 out of 10, Excellent, (1004)
"Great staff"
The price is AU$132
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn & Suites
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.

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?

Hidden gem with water and golf course views! Bike ride to downtown!: This holiday home rental outside Greensboro is located next to a golf course, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and 1 hot 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 wider area, you’ll find Harrington Raceway and Casino and Killens Pond 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.