Vacation rentals in Rockingham

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Top-rated vacation rentals in Rockingham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Southern Pines

4.97 out of 5 average rating, 209 reviews

Historic 1921 Southern Pines Carriage House

Modern convenience & Roaring 20's charm at this Tudor Revival Carriage House surrounded by 1 acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Private entrance, patio & living space on a secluded property a mile from downtown Southern Pines' shops & 5 miles from Pinehurst. Enjoy area golf courses or stop in when visiting Penick Village or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO parties, NO ILLEGAL DRUGS.

Apr 5 – 12

R1,750 ZAR per night
Guest favorite

Farm stay in Vass

4.94 out of 5 average rating, 126 reviews

Peaceful Horse Farm Retreat

Anahata is a quiet farm retreat dedicated to peace and healing. You’ll stay in our Hunt Box - a spacious studio apartment over the barn with pasture view and fully equipped kitchen. There is space to roam and animals to greet. Please read the full listing prior to booking to ensure that this is the right place for you. For more pics, check out our Insta @anahatafarm. NO third-party bookings - please do not book this room unless you will be the one staying here. NO SMOKING. All are welcome here.

Jul 12 – 19

R1,978 ZAR per night
Guest favorite

Apartment in Laurinburg

4.98 out of 5 average rating, 328 reviews

Chauffeur’s Apartment on Historic Property

Be our guest in our cozy and comfortable apartment that has everything needed for a relaxing stay. Enjoy the former chauffeur's quarters located on the grounds of our listed historic property with a view of the tranquil courtyard garden of the Manor House. The kitchen is complete and the comfortable full-sized bed should provide a good night's rest. Downtown is within walking distance. There are multiple seating areas to enjoy the gardens on the one acre grounds shared with the main property.

May 29 – Jun 5

R1,982 ZAR per night

Popular amenities for Rockingham vacation rentals

Other great vacation rentals in Rockingham

Guest favorite

Apartment in Hamlet

4.91 out of 5 average rating, 57 reviews

Lovely 2-bedroom apartment near downtown Hamlet

Aug 4 – 11

R2,107 ZAR per night
Guest favorite

Home in Ellerbe

5.0 out of 5 average rating, 6 reviews

the Loblolly getaway

May 24 – 31

R1,869 ZAR per night
Guest favorite

Home in Rockingham

4.93 out of 5 average rating, 41 reviews

Completely Renovated 3-Bedroom Brick Home

May 4 – 11

R3,414 ZAR per night
Guest favorite

Home in Rockingham

5.0 out of 5 average rating, 11 reviews

Spacious & Cozy Home New Kitchen & Bathrooms

Aug 14 – 21

R3,865 ZAR per night
Superhost

Home in Rockingham

4.81 out of 5 average rating, 52 reviews

Spacious 3 bedroom house 6 acres with water view

Feb 15 – 22

R4,768 ZAR per night
Guest favorite

Cabin in Morven

5.0 out of 5 average rating, 47 reviews

Sneedsboro Cabin

Dec 12 – 19

R1,781 ZAR per night
Guest favorite

Cottage in Mount Gilead

4.9 out of 5 average rating, 29 reviews

Cute Private Home Close to Tillery-Boat & Pets OK!

Nov 16 – 23

R1,603 ZAR per night
Guest favorite

Home in Cheraw

4.9 out of 5 average rating, 49 reviews

Brown’s Guest House

Aug 6 – 13

R2,293 ZAR per night
Guest favorite

Condo in Jackson Springs

4.94 out of 5 average rating, 62 reviews

Charming Condo with Golf View, steps from pool.

Jul 23 – 30

R2,007 ZAR per night
Guest favorite

Cottage in Chesterfield

5.0 out of 5 average rating, 63 reviews

Kindred Shanty ~ Rural House In Chesterfield

Nov 25 – Dec 2

R2,038 ZAR per night
Superhost

Home in Chesterfield

4.88 out of 5 average rating, 8 reviews

“ I’m Going to Carolina”

Jan 16 – 23

R1,968 ZAR per night
Superhost

Home in Laurel Hill

4.8 out of 5 average rating, 5 reviews

NC Charm: Laurel Hill Hideaway

Aug 28 – Sep 4

R1,809 ZAR per night

Destinations to explore