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Jackson Springs Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Jackson Springs vacation rentals

A large house with a covered porch, stone foundation, and a well-maintained lawn with a golf course in the background.

1. Quiet Condo on Golf Course with EV Plug near Pinehurst

Quiet Condo on Golf Course with EV Plug near Pinehurst
Foxfire
9.4 out of 10, Exceptional, (22 reviews)
"We had a wonderful stay here! The house was very clean, spacious, and had plenty of room for our family of 5. Our children especially loved the convenience of being right next to the pickleball court. The host was extremely accommodating and always quick to respond to any questions we had. We truly enjoyed our stay and would absolutely recommend this rental to anyone looking for a comfortable and family friendly place to stay!"
United States
Britany H.
$242 nightly
The price is $273
Oct 4 - Oct 5
Total with taxes and fees
Quiet Condo on Golf Course with EV Plug near Pinehurst
A wooden dock extending into a calm lake surrounded by trees with autumn foliage.

2. 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.
$1,422 nightly
The price is $1,607
Oct 14 - Oct 15
Total with taxes and fees
Ultimate Golf Trip House - Pool & Pickleball
A modern kitchen with a white island, yellow bar stools, stainless steel appliances, and large windows with curtains.

3. The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
Pinehurst
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
$240 nightly
The price is $271
Oct 5 - Oct 6
Total with taxes and fees
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a large window with a view of the outside.

4. The Perfect Lie in Pinehurst! A golfer's paradise!

The Perfect Lie in Pinehurst! A golfer's paradise!
Pinehurst
9.8 out of 10, Exceptional, (78 reviews)
"Wonderful stay and great experience with our host!"
United States
Matthew D.
$261 nightly
The price is $295
Oct 5 - Oct 6
Total with taxes and fees
The Perfect Lie in Pinehurst! A golfer's paradise!
A lake with houses and a dock.

5. Stunning Lake front views in Pinehurst with a pool!

Stunning Lake front views in Pinehurst with a pool!
Pinehurst
10.0 out of 10, Exceptional, (110 reviews)
"Great place to stay!"
United States
Jody W.
$280 nightly
The price is $316
Oct 25 - Oct 26
Total with taxes and fees
Stunning Lake front views in Pinehurst with a pool!
A modern kitchen with a double sink, a coffee maker, and a variety of snacks on the counter.

6. Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (54 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
$199 nightly
The price is $225
Oct 22 - Oct 23
Total with taxes and fees
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
A living room with a sofa, armchair, coffee table, and a view through a glass door to the outside.

7. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.6 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Lauren
$167 nightly
The price is $189
Oct 5 - Oct 6
Total with taxes and fees
Studio Seven at Pine Valley
A modern kitchen with a central island, stainless steel appliances, and a stone tile floor.

8. Lakeside Condo on Pinehurst #5

Lakeside Condo on Pinehurst #5
Pinehurst
10.0 out of 10, Exceptional, (61 reviews)
"The place has an awesome location.. you can walk to the clubhouse if you wanted to... would definitely recommend this rental and i might do it again at some point "
United States
Jason W.
$268 nightly
The price is $303
Oct 6 - Oct 7
Total with taxes and fees
Lakeside Condo 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, (51 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
$305 nightly
The price is $345
Oct 28 - Oct 29
Total with taxes and fees
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Drum & Quill Public House with outdoor seating and a brick facade.

10. Newly Renovated Property.

Newly Renovated Property.
Pinehurst
10.0 out of 10, Exceptional, (154 reviews)
"Incredible location and value. Would recommend this property to anyone looking to visit Pinehurst"
United States
CRAIG E.
$264 nightly
The price is $298
Oct 6 - Oct 7
Total with taxes and fees
Newly Renovated Property.
A modern bedroom with a bed, a desk, and a balcony with a chair.

11. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (65 reviews)
"Always a wonderful stay!"
United States
Whitney S.
$232 nightly
The price is $262
Nov 2 - Nov 3
Total with taxes and fees
The Lucky Lie - Entire Condo in Pinehurst
A bedroom with a bed, a nightstand, a lamp, a large mirror, a wicker basket, and a view of the outdoors through a sliding door.

12. 3BD Spacious Pinehurst Retreat. Pool & Arcade Games. Near Resort & Fair Barn.

3BD Spacious Pinehurst Retreat. Pool & Arcade Games. Near Resort & Fair Barn.
Pinehurst
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay. Thanks Brittany for all the hospitality!! Everything was great!!!"
United States
Steve L.
$307 nightly
The price is $347
Oct 5 - Oct 6
Total with taxes and fees
3BD Spacious Pinehurst Retreat. Pool & Arcade Games. Near Resort & Fair Barn.
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden dining area with a view of greenery.

13. COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
Pinehurst
10.0 out of 10, Exceptional, (41 reviews)
"Great stay! "
United States
Kendahl M.
$332 nightly
The price is $375
Oct 6 - Oct 7
Total with taxes and fees
COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

14. 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, (37 reviews)
"Amazing place!"
United States
Jeremy
$256 nightly
The price is $289
Oct 6 - Oct 7
Total with taxes and fees
Isle of the Pines, 1 mile from The Village of Pinehurst!
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

15. A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!

A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!
Pinehurst
9.8 out of 10, Exceptional, (88 reviews)
"The place was great. Convenient location and a great house. We had an awesome trip. "
United States
Matt M.
$661 nightly
The price is $746
Oct 4 - Oct 5
Total with taxes and fees
A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!
A dining area with a poker table, chairs, a hanging light fixture, and a view of the outside through large windows.

16. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Pinehurst
9.4 out of 10, Exceptional, (19 reviews)
"Great place for a short golf getaway "
United States
Jay G.
$293 nightly
The price is $331
Oct 15 - Oct 16
Total with taxes and fees
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
A modern living room with a fireplace, a dining area, and a sofa.

17. NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn

NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
Pinehurst
10.0 out of 10, Exceptional, (17 reviews)
"This place was absolutely amazing. I would definitely stay here again. Very clean and comfortable quiet and the location couldn’t have been better."
United States
Angela S.
$288 nightly
The price is $325
Oct 6 - Oct 7
Total with taxes and fees
NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

18. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (99 reviews)
"This is a great house to stay at when in Pinehurst. Our family enjoyed our stay."
United States
Robert D.
$416 nightly
The price is $471
Oct 5 - Oct 6
Total with taxes and fees
NEW! Pinehurst Eight Sleeps 10!
A modern kitchen with a dining area, a flat-screen TV, and a coffee maker.

19. To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (92 reviews)
"I would highly recommend staying here when visiting Pinehurst and Southern Pines. It was one of the best VRBO experiences we have enjoyed."
United States
Jenny I.
$200 nightly
The price is $226
Oct 7 - Oct 8
Total with taxes and fees
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
A spacious living room with a blue sofa, a dining area with a wooden table, and a kitchen with modern appliances.

20. 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.
$416 nightly
The price is $471
Oct 5 - Oct 6
Total with taxes and fees
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
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 Jackson Springs Hotel Reviews

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

10/10 Excellent
"Staff were helpful. Location was good."
Joshua 3-night trip
Posted 9 hours ago
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Find out more about Jackson Springs

Everything you need to know about Jackson Springs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jackson Springs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jackson Springs vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jackson Springs vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jackson Springs. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Jackson Springs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jackson Springs rentals

At Expedia, we put the best Jackson Springs vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Jackson Springs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jackson Springs vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jackson Springs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Jackson Springs?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Jackson Springs, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Jackson Springs has to offer?

Pristine Pinehurst #6 home - Gated backyard - 2 min to courses. Handicap Access: You might want to consider this vacation home rental near Jackson Springs, which is located next to a golf course and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Jackson Springs?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Jackson Springs stay.

What’s there to see and do in Jackson Springs?

While exploring the area, visit family-friendly sights like World Golf Hall of Fame, or get outside and enjoy nature at Pinehurst Lake. In the larger area, you’ll find Foxfire Golf and Country Club and Pinehurst Resort.

What’s a vacation rental in Jackson Springs like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Jackson Springs. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family gatherings.