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Our top choices for Simpsonville vacation homes
1. Southern Charm Townhome
Southern Charm TownhomeSimpsonville
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and safe location. Super cute interior decorations and comfortable. Also a great location for us to visit family who are local. Absolutely would stay again."
Brianna F.
The price is CA $156
CA $526 total
includes taxes & fees
Nov 9 - Nov 10
2. 3/2 Retreat, Walk to DT Simpsonville, Fire Pit
3/2 Retreat, Walk to DT Simpsonville, Fire PitSimpsonville
The price is CA $209
CA $578 total
includes taxes & fees
Nov 18 - Nov 19
3. Historic 3BR with Porch & Fire Pit near Downtown
Historic 3BR with Porch & Fire Pit near DowntownSimpsonville
9.0 out of 10, Wonderful, (9 reviews)
"Close to town easy walk to dinner"
Gary g.
The price is CA $193
CA $539 total
includes taxes & fees
Nov 9 - Nov 10
4. HOT TUB, Community Pool, AC, 5-Bedroom Oasis in Simpsonville
HOT TUB, Community Pool, AC, 5-Bedroom Oasis in SimpsonvilleSimpsonville
10.0 out of 10, Exceptional, (2 reviews)
"Lovely house! Everything was exactly as described and it was the perfect location for a girls’ weekend trip! The beds were all comfortable and the common areas were spacious with lots of seating options. We will definitely book again!"
Meghann P.
The price is CA $292
CA $600 total
includes taxes & fees
Nov 5 - Nov 6
5. Spacious 5-BR Retreat in Simpsonville, SC – Perfect for Gatherings & Getaways
Spacious 5-BR Retreat in Simpsonville, SC – Perfect for Gatherings & GetawaysSimpsonville
9.8 out of 10, Exceptional, (14 reviews)
"Large house which fit our needs"
colleen b.
The price is CA $346
CA $496 total
includes taxes & fees
Nov 5 - Nov 6
6. Luxury Retreat & Heated Pool Downtown Simpsonville
Luxury Retreat & Heated Pool Downtown SimpsonvilleSimpsonville
9.8 out of 10, Exceptional, (18 reviews)
"This house was great including a great pool area, comfortable beds and linens, great outdoor pizza oven, wonderful ceiling fans (inside and out), and a great game area upstairs! We were a family ranging in ages from 27- 82 and everyone enjoyed themselves. Lots to do in the area and close to Greenville."
Tammy L.
The price is CA $394
CA $697 total
includes taxes & fees
Nov 5 - Nov 6
7. Entire Duplex with Backyard Firepit | Sleeps 12 | Great for Groups and Families!
Entire Duplex with Backyard Firepit | Sleeps 12 | Great for Groups and Families!Simpsonville
The price is CA $386
CA $997 total
includes taxes & fees
Nov 5 - Nov 6
8. Cozy Mauldin Hill by Brick and Home
Cozy Mauldin Hill by Brick and HomeSimpsonville
9.8 out of 10, Exceptional, (6 reviews)
"This house was perfect for us, close to everything, and very comfortable!"
Jessica A.
The price is CA $589
CA $888 total
includes taxes & fees
Nov 20 - Nov 21
9. Drury Heights - Cozy & Stylish Getaway
Drury Heights - Cozy & Stylish GetawayMauldin
The price is CA $217
CA $504 total
includes taxes & fees
Nov 8 - Nov 9
10. Hot Tub & Mini Golf · Fenced Yard · Covered Patio for Groups · Sleeps8 · Pets OK
Hot Tub & Mini Golf · Fenced Yard · Covered Patio for Groups · Sleeps8 · Pets OKGreenville
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The house was cute, and the host thought of everything. Our little pups enjoyed the backyard, and we enjoyed the outdoor seating areas. Thank you!!!"
Shelley S.
The price is CA $186
CA $675 total
includes taxes & fees
Nov 5 - Nov 6
11. Private pickleball court, game room, sunroom & pool — near Greenville
Private pickleball court, game room, sunroom & pool — near GreenvilleMauldin
10.0 out of 10, Exceptional, (12 reviews)
"Very clean plenty of space in a quiet neighborhood FAMILY & YOUNG ONES enjoyed themselves."
Michael J.
The price is CA $469
CA $1,123 total
includes taxes & fees
Nov 9 - Nov 10
12. Spacious 4-bedroom house in serene Greenville with AC
Spacious 4-bedroom house in serene Greenville with ACGreenville
The price is CA $248
CA $418 total
includes taxes & fees
Nov 8 - Nov 9
13. Family Poolside Oasis & Guest Suite 5BR/4BA & YARD
Family Poolside Oasis & Guest Suite 5BR/4BA & YARDGreenville
10.0 out of 10, Exceptional, (5 reviews)
"House was accommodating for our large group "
Sterling N.
The price is CA $342
CA $934 total
includes taxes & fees
Nov 9 - Nov 10
14. Hope on the Enoree River w/ Fire Pit & Chef's Kitchen
Hope on the Enoree River w/ Fire Pit & Chef's KitchenWoodruff
10.0 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay here! The owner was quick with responses, check in was super easy and the kids loved going down to the river to play and fish! The house was so clean and all the “extras” that they provide were fantastic! If we are back in the area, we will definitely stay here again!!"
Allison S.
15. Greenville 3BR Retreat | Screened Porch | 4.85*
Greenville 3BR Retreat | Screened Porch | 4.85*Greenville
The price is CA $334
CA $781 total
includes taxes & fees
Nov 7 - Nov 8
16. Apt. near Downtown Greenville (2BR/1BA, 3 beds)
Apt. near Downtown Greenville (2BR/1BA, 3 beds)Greenville
10.0 out of 10, Exceptional, (12 reviews)
"It was clean and quiet..I will stay here again. "
Kimberly S.
The price is CA $132
CA $215 total
includes taxes & fees
Nov 18 - Nov 19
17. The Blue Bungalow by Unity Park - Newly Renovated
The Blue Bungalow by Unity Park - Newly RenovatedWoodside Cotton Mill Village Historic District
9.8 out of 10, Exceptional, (114 reviews)
"Fully equipped, comfortable beds…everything to make for an enjoyable stay. "
Ron E.
The price is CA $103
CA $300 total
includes taxes & fees
Nov 17 - Nov 18
18. Charming Greenville Home • Near Downtown & GSP
Charming Greenville Home • Near Downtown & GSPGreenville
The price is CA $189
CA $461 total
includes taxes & fees
Nov 5 - Nov 6
19. Modern 2-room apartment • Perfect for Work & Family — 6 Minutes from Downtown Greenville
Modern 2-room apartment • Perfect for Work & Family — 6 Minutes from Downtown GreenvilleGreenville
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay in this super cute home! It was perfect for what we needed while attending a conference in town for a few days. We really appreciated the heads up about the construction in the neighborhood from the host."
Anonymous traveller
The price is CA $161
CA $310 total
includes taxes & fees
Nov 17 - Nov 18
20. The Westfield - Cozy Downtown Greer Retreat
The Westfield - Cozy Downtown Greer RetreatGreer
9.4 out of 10, Exceptional, (11 reviews)
"Very nice place! Everything was just what we needed. Perfect size for 3 people. Location was very convenient being able to walk downtown to some nice restaurants. Would definitely stay again!!"
Julie M.
The price is CA $90
CA $238 total
includes taxes & fees
Dec 2 - Dec 3
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.
Learn more about Simpsonville
Heritage Park's amphitheater hosts summer concerts where locals spread blankets under starry skies. Explore the charming downtown district, then cycle the Swamp Rabbit Trail connecting to nearby Greenville's vibrant food scene.
Top reviews in Simpsonville
Holiday Inn Express & Suites Greenville SE - Simpsonville by IHG
Holiday Inn Express & Suites Greenville SE - Simpsonville by IHGSimpsonville
10/10 Excellent
The mattress was a bit uncomfortable but the pillows were very comfortable
Cindy
