Greensboro Vacation Rentals

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Aug 29 - Aug 31
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Oct 17 - Oct 19

Browse Select Greensboro Vacation Homes

Our top choices for Greensboro vacation homes

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

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

9.8 out of 10, Exceptional, (22)
"It was a awesome great comfy 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
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (18)
"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
Cozy cottage on the Miller farm.
Exterior

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (229)
"Awesome place. "
Cozy cottage on the Miller farm.
Peaceful Queenstown Home w/ Deck & Grill!
Interior

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Enjoyed this lovely and comfortable home tucked away in a private location close to amenities. "
Peaceful Queenstown Home w/ Deck & Grill!
Luxury Treehouse with Large Deck
Interior

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (8)
"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
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Property grounds

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

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

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Modern Country Home with Pool and Game Room
Property grounds

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
Guest suite in the woods with private entry
Exterior

Guest suite in the woods with private entry

10.0 out of 10, Exceptional, (42)
"Great location and very clean! Would stay again"
Guest suite in the woods with private entry
Grasonville Home w/ Private Pool on the Water
Pool

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

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $347
CA $581 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Estate w Private Pier, Game Room & Bar
Game room

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (30)
"Overall, our stay was fantastic. The weather was absolutely magnificent the entire stay."
Waterfront Estate w Private Pier, Game Room & Bar
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

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

10.0 out of 10, Exceptional, (81)
"Loved our stay!"
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina

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

10.0 out of 10, Exceptional, (89)
"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
Poe Themed Home Close to Beaches and DE Turf
Outdoor dining

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 CA $225
CA $386 total
includes taxes & fees
Aug 24 - Aug 25
Poe Themed Home Close to Beaches and DE Turf
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Property grounds

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

9.8 out of 10, Exceptional, (10)
"We loved our stay! "
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
RELAX- Eastern Shore Creek Home - 6 Guests
Smart TV, fireplace

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (3)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
RELAX- Eastern Shore Creek Home - 6 Guests
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

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 CA $273
CA $622 total
includes taxes & fees
Aug 25 - Aug 26
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Exterior detail

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
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Great stay, very clean!"
Boyce II and Michelle 1-night trip
Posted 2 days ago
Bally's Dover Casino Resort