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Vacation Homes in Greensboro

Our top choices for Greensboro vacation homes

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

9.8 out of 10, Exceptional, (24)
"We loved this property and hopefully will be back next year. Was amazing having room to spread out and such a nice clean house! "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

9.4 out of 10, Exceptional, (28)
"It was a great option for our Lacrosse weekend!"
Lee's Place Brand New 2BR Townhouse w/free parking

Delaware Turf Bungalow’s Sister!

10.0 out of 10, Exceptional, (1)
"This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was...
Delaware Turf Bungalow’s Sister!

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

9.6 out of 10, Exceptional, (22)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal Beach)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.6 out of 10, Exceptional, (12)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is SAR 938
SAR 1,547 total
includes taxes & fees
19 Sep - 20 Sep
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"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

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"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

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

10.0 out of 10, Exceptional, (2)
"Located in a quiet area. Beautiful place. Wish we could have stayed longer. An information sheet/welcome booklet could have been helpful in learning how to start the fireplace and the wifi info."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

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

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is SAR 739
SAR 1,670 total
includes taxes & fees
1 Oct - 2 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Guest suite in the woods with private entry

10.0 out of 10, Exceptional, (43)
"Great location and very clean! Would stay again"
Guest suite in the woods with private entry

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (9)
"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, (61)
"Wonderful setting, cabin feel with modern amenities. Really enjoyed the quiet, the pool, hot tub, and trails. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

10.0 out of 10, Exceptional, (5)
"We rented for my daughter’s graduation from Washington college. Wonderful home that was decorated great with a perfect location!!! "
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (5)
"This property was in a great location for attending the Waterfowl festival. The host thought about each detail and our stay was more than comfortable. "
Cozy 2BR Home near Idlewild Park

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (9)
"This is a place that I we can’t wait to go back to!! Everything was so unique and done up with thought. You have to go and read the beautiful story behind the “Tree House” "
Luxury Treehouse with Large Deck

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

10.0 out of 10, Exceptional, (93)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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