Holiday Homes in Jackson Springs

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Apartments
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Condos
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Jackson Springs holiday homes

A wooden dock extending into a calm lake surrounded by trees with autumn foliage.

1. Ultimate Golf Trip House - Pool & Pickleball

Ultimate Golf Trip House - Pool & Pickleball
Foxfire
10.0 out of 10, Exceptional, (4 reviews)
"Awesome place!"
United States
Brendan T.
The price is €1,394
includes taxes & fees
15 Nov - 16 Nov
Ultimate Golf Trip House - Pool & Pickleball
Miscellaneous

2. The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
10.0 out of 10, Exceptional, (23 reviews)
"My husband and I had a wonderful stay in this home. The house had everything we needed and the location was great!"
United States
Kathy B.
The price is €211
includes taxes & fees
7 Dec - 8 Dec
The McCaskill Cottage in the Village of Pinehurst!
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

3. Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Taylortown
8.0 out of 10, Very good, (7 reviews)
"Really pretty place. The loft was very very small. I’m 5’4” and had to bend at the waist to get to the bed. Wish the front door had a way to cover it (full see through glass). The beds and couch were very comfortable. House was clean and decorated very nicely. Bathroom is a dream!!"
United States
Matthew C.
The price is €130
includes taxes & fees
7 Dec - 8 Dec
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

4. Isle of the Pines, 1 mile from The Village of Pinehurst!

Isle of the Pines, 1 mile from The Village of Pinehurst!
Pinehurst
10.0 out of 10, Exceptional, (38 reviews)
"Great place, great location, great hosts."
United States
Aaron Z.
The price is €356
includes taxes & fees
19 Nov - 20 Nov
Isle of the Pines, 1 mile from The Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

5. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (43 reviews)
"Great location to get to all of the golf courses we played. Plenty of room for the 6 of us. Host very attentive."
United States
James N.
The price is €390
includes taxes & fees
6 Dec - 7 Dec
The Mulligan!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

6. Polo & Pine Retreat

Polo & Pine Retreat
Pinehurst
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and looked exactly like the pictures. It was a great value and we enjoyed our stay."
United States
kevin t.
The price is €327
includes taxes & fees
7 Dec - 8 Dec
Polo & Pine Retreat
Living area

7. Beautiful 1 Bed Condo on Pinehurst Course No.5!

Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pinehurst
9.0 out of 10, Wonderful, (18 reviews)
"Enjoyed our time here!"
United States
Scot W.
The price is €226
includes taxes & fees
13 Nov - 14 Nov
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A modern outdoor living area with wicker furniture, a glass coffee table, and a large window offering a view of trees.

8. The Tin Cup on Pinehurst #5

The Tin Cup on Pinehurst #5
Pinehurst
9.8 out of 10, Exceptional, (43 reviews)
"Perfect spot for short trip to pinehurst"
United States
Douglas R.
The Tin Cup on Pinehurst #5
A spacious living area with a wooden coffee table, a sofa, and a dining table. There is a green-framed window and a wall-mounted artwork.

9. Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!

Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Pinehurst
10.0 out of 10, Exceptional, (52 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
The price is €284
includes taxes & fees
1 Dec - 2 Dec
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

10. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (103 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is €380
includes taxes & fees
16 Nov - 17 Nov
NEW! Pinehurst Eight Sleeps 10!
A spacious living room with a blue sofa, a dining area with a wooden table, and a kitchen with modern appliances.

11. A Home in One ⛳️ Sleeps 10 & 🎱 Table!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (44 reviews)
"Great house and location. "
United States
Billy P.
The price is €384
includes taxes & fees
16 Nov - 17 Nov
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

12. Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Pinehurst
8.8 out of 10, Excellent, (18 reviews)
"a little dated but excellent location"
United States
Anonymous traveller
The price is €207
includes taxes & fees
13 Dec - 14 Dec
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
A wooden deck with a view of a lake and trees, a bench, and a table.

13. Cozy 1-bedroom 1 bath barndominium on 60 acre farm

Cozy 1-bedroom 1 bath barndominium on 60 acre farm
Ellerbe
The price is €182
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom 1 bath barndominium on 60 acre farm
A rustic wooden cabin with a black door, a window with colorful mugs, and a welcome mat on the deck.

14. Loft Cottage on Ridge<br>? Short & Extended Stays?

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
9.8 out of 10, Exceptional, (48 reviews)
"Great location in the middle of town but still quiet. It was just what we needed for the weekend. We visit the area regularly and would book again!"
United States
Yasmine G.
The price is €123
includes taxes & fees
13 Dec - 14 Dec
Loft Cottage on Ridge<br>? Short & Extended Stays?
A covered outdoor patio with a fire pit, seating area, and a grill.

15. Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf

Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
Pinehurst
9.4 out of 10, Exceptional, (19 reviews)
"Great place for a family or golf getaway! "
United States
Mike S.
The price is €352
includes taxes & fees
7 Dec - 8 Dec
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
A spacious sunroom with a sectional sofa, large windows, and a ceiling fan.

16. Pinehurst Retreat - Near No. 2

Pinehurst Retreat - Near No. 2
Pinehurst
10.0 out of 10, Exceptional, (15 reviews)
"Great property! "
United States
Anonymous traveller
The price is €377
includes taxes & fees
18 Nov - 19 Nov
Pinehurst Retreat - Near No. 2
A modern kitchen with white cabinets, a granite countertop, and three grey bar stools.

17. Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!

Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
Pine Hurst
10.0 out of 10, Exceptional, (53 reviews)
"Great host, great house. Plenty of amenities. This was our third time staying at this location, we will be back"
United States
Randy F.
The price is €388
includes taxes & fees
19 Nov - 20 Nov
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
A single-story house with a gray exterior, white trim, and a front porch.

18. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is €155
includes taxes & fees
15 Nov - 16 Nov
Walkable Cottage, Pet Friendly with Fenced Patio
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

19. The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit

The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit
Pinehurst
10.0 out of 10, Exceptional, (33 reviews)
"Great place. Would stay again. "
United States
Keir S.
The price is €413
includes taxes & fees
15 Nov - 16 Nov
The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit
A modern living room with a fireplace, grey sofas, a coffee table, and a flat-screen TV mounted on the wall.

20. Spacious Retreat w/ Game Room and Modern Amenities

Spacious Retreat w/ Game Room and Modern Amenities
Pinehurst
9.4 out of 10, Exceptional, (3 reviews)
"Great place to stay."
United States
Larry H.
The price is €646
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat w/ Game Room and Modern Amenities
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 reviews in Jackson Springs

A spacious kitchen with dark wooden cabinets, a marble island, and a central island with a sink. There are multiple pendant lights and a large window providing natural light.
Homewood Suites by Hilton Olmsted Village (near Pinehurst)

Homewood Suites by Hilton Olmsted Village (near Pinehurst)

Homewood Suites by Hilton Olmsted Village (near Pinehurst)
Pinehurst

8/10 Good

whether was amazing, a paradise for Golfer.
Ireland
Anonymous traveller
Reviewed August 17, 2019
Homewood Suites by Hilton Olmsted Village (near Pinehurst)