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Five Points Vacation Rentals

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  • Upfront pricing

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Five Points vacation rentals

Interior

Near Carolina Horse Park Family Friendly 4BR Home w/ Poker Room & Bocce

Near Carolina Horse Park Family Friendly 4BR Home w/ Poker Room & Bocce
Raeford
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful property! I look forward to staying there again for the next horse show. "
United States
Kathryn G.
$411 nightly
The price is $439
Aug 10 - Aug 11
Total with taxes and fees
Near Carolina Horse Park Family Friendly 4BR Home w/ Poker Room & Bocce
Desk, iron/ironing board, WiFi (free), bed sheets

The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (63 reviews)
"Clean and comfortable. Hosts were very helpful and friendly. Will definitely stay here again"
United States
Andrew
$226 nightly
The price is $255
Aug 11 - Aug 12
Total with taxes and fees
The Lucky Lie - Entire Condo in Pinehurst
Private kitchen

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, (17 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
$269 nightly
The price is $304
Jul 21 - Jul 22
Total with taxes and fees
The McCaskill Cottage in the Village of Pinehurst!
1 bedroom, desk, iron/ironing board, free WiFi

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, (84 reviews)
"Great all around stay, best feature of this place is location. You can walk right over to Pinehurst Golf Club, their dining options, etc. "
United States
JD A.
$180 nightly
The price is $203
Aug 5 - Aug 6
Total with taxes and fees
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Dining

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, (70 reviews)
"Comfortably furnished and a great location. Perfect for our needs!"
United States
Jenni F.
$243 nightly
The price is $275
Aug 3 - Aug 4
Total with taxes and fees
The Perfect Lie in Pinehurst! A golfer's paradise!
Dining

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, (50 reviews)
"Perfect location, perfect size....simple furnishings, but exactly what we needed for the trip!"
United States
Sue M.
$237 nightly
The price is $268
Jul 15 - Jul 16
Total with taxes and fees
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
Dining

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, (18 reviews)
"Great place for a short golf getaway "
United States
Jay G.
$302 nightly
The price is $341
Aug 3 - Aug 4
Total with taxes and fees
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
WiFi (free), bed sheets

Located in # 6 golf community, close to First Health Moore Regional Hospital.

Located in # 6 golf community, close to First Health Moore Regional Hospital.
Pinehurst
10.0 out of 10, Exceptional, (75 reviews)
"It was a great place to stay. I would definitely recommend to anyone. Host very friendly and helpful! "
United States
Krystal B.
$135 nightly
The price is $153
Jul 15 - Jul 16
Total with taxes and fees
Located in # 6 golf community, close to First Health Moore Regional Hospital.
Interior

19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Pinehurst
9.0 out of 10, Wonderful, (62 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property is very well located in connection to many nice restaurants and shopping opportunities as well as it being quiet and low key which was great for us"
United States
Rita C.
$193 nightly
The price is $207
Jul 16 - Jul 17
Total with taxes and fees
19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Exterior detail

The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (18 reviews)
"This is a favorite place for us to stay when in Southern Pines. It is lovely, comfortable, the host is very helpful and the location is great. "
United States
Tracey W.
$186 nightly
The price is $209
Jul 15 - Jul 16
Total with taxes and fees
The Cottage at Knollwood Manor
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Taylortown
$131 nightly
The price is $148
Jul 15 - Jul 16
Total with taxes and fees
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
TV

House in the Pines - Tiny Home Near Southern Pines

House in the Pines - Tiny Home Near Southern Pines
Vass
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy! Beat our expectations and then some. 2 mini splits so temperature control can be adjusted in the bedroom and in the living room (we liked that). Felt like home and the area and property are beautiful! Host was extremely responsive and friendly. We had a wonderful experience 👍 Thank you!"
United States
Robert
$202 nightly
The price is $229
Jul 15 - Jul 16
Total with taxes and fees
House in the Pines - Tiny Home Near Southern Pines
Fridge, microwave, oven, stovetop

Lakeside Condo on Pinehurst #5

Lakeside Condo on Pinehurst #5
Pinehurst
10.0 out of 10, Exceptional, (52 reviews)
"Great location, spotless, easy check in and wonderful communication. "
United States
Josh H.
$265 nightly
The price is $300
Aug 12 - Aug 13
Total with taxes and fees
Lakeside Condo on Pinehurst #5
Property grounds

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

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
10.0 out of 10, Exceptional, (38 reviews)
"The kitchen was fully equipped and very clean. The place was nicely furnished and comfortable! Host was very helpful and provided easy check in/out directions and recommendations for dining and entertainment!We thoroughly enjoyed our stay!"
United States
Jerri H.
$157 nightly
The price is $164
Aug 3 - Aug 4
Total with taxes and fees
Loft Cottage on Ridge<br>? Short & Extended Stays?
Property grounds

Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm

Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm
Southern Pines
9.8 out of 10, Exceptional, (76 reviews)
"Overnight stay, beautiful horse ranch in the country"
United States
gAil h.
$195 nightly
The price is $220
Jul 20 - Jul 21
Total with taxes and fees
Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm
TV

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.
$219 nightly
The price is $247
Jul 15 - Jul 16
Total with taxes and fees
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Fridge, microwave, oven, stovetop

NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.6 out of 10, Exceptional, (97 reviews)
"Almost new home. Very clean and well supplied. Great access to the Pinehurst/Southern Pines area. Nice quiet neighborhood. "
United States
Timothy L.
$458 nightly
The price is $518
Jul 20 - Jul 21
Total with taxes and fees
NEW! Pinehurst Eight Sleeps 10!
Dining

The Mulligan Manor - 1BR/1BA Condo in Pinehurst

The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (19 reviews)
"Great stay!"
United States
Chris F.
$232 nightly
The price is $262
Jul 15 - Jul 16
Total with taxes and fees
The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Exterior

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)
"The condo was perfect for our stay. Very comfortable, clean and well supplied. It is a 10-20 minute drive anywhere, not to mention the view of hole 18 on the red course. We loved being right in front of the pickle ball courts as well, which we definitely enjoyed. "
United States
Kim C.
$240 nightly
The price is $271
Jul 15 - Jul 16
Total with taxes and fees
Quiet Condo on Golf Course with EV Plug near Pinehurst
Living area

Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.4 out of 10, Exceptional, (8 reviews)
"Great stay"
United States
Lauren
$171 nightly
The price is $193
Jul 19 - Jul 20
Total with taxes and fees
Studio Seven at Pine Valley
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 Five Points Hotel Reviews

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

10/10 Excellent
"It wS a nice place to stay. Close to family."
Tina 2-night trip
Posted 5 hours ago
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Find out more about Five Points

Everything you need to know about Five Points 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 Five Points 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 Five Points vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Five Points vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Five Points. 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 Five Points 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 $203 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 Five Points rentals

At Expedia, we put the best Five Points 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 Five Points 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 Five Points 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 Five Points. 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 Five Points?

Yes, we give you a choice of vacation rentals close to popular points of interest in Five Points, or you can select a secluded option if you want a relaxing place to stay. Five Points is known for its golf courses.

What are some of the best vacation rentals in Five Points?

Beautiful 1920's Craftsman-Downtown Southern Pines: Visitors like this Five Points vacation home rental. It 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 3 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 Five Points?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Five Points stay.

What can I see and do in Five Points?

While you're exploring the area, Pinehurst Lake and Sandhills Horticultural Gardens are a couple of picturesque spots to get outside and enjoy nature. Carolina Horse Park and Deercroft Golf Course are other places to visit while you're in town.

What are vacation rentals like in Five Points?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Five Points. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for small groups.