Search Vacation Homes in Greensboro

  • 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

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 79 Vacation Homes in Greensboro with updated reviews, rates, and availability.

Lee's Place Brand New 2BR Townhouse w/free parking

9.4 out of 10, Exceptional, (20)
"Very enjoyable stay!"
Lee's Place Brand New 2BR Townhouse w/free parking

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

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

10.0 out of 10, Exceptional, (86)
"My family (9 of us ages 30-63) stayed at the sunset house for what have been our 30th family vacation. This house was perfect. Great location to St Michael’s, Easton and Oxford made for "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

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

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

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.8 out of 10, Exceptional, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"
Stylish Home on the Choptank River (with Tidal Beach)

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (25)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"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. "
Gorgeous Creek Side Ranch-Style Estate With Dock

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

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Modern Country Home with Pool and Game Room

9.4 out of 10, Exceptional, (6)
"Nice place. Well accommodated."
Modern Country Home with Pool and Game Room

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (11)
"Perfect for a family wedding weekend"
River Front, Private Single Family Home

Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf

10.0 out of 10, Exceptional, (7)
"Great location, and beautiful property. Nicely equipped."
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf

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

9.8 out of 10, Exceptional, (9)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Private Yard: Pet-Friendly Home in Dover

10.0 out of 10, Exceptional, (12)
"Quiet location, clean and big. "
Private Yard: Pet-Friendly Home in Dover

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
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.
Don't see what you're looking for?
See all available properties in Greensboro
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Greensboro

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

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

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

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

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private 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.