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Compare 382 Vacation Homes in Rockingham with updated reviews, rates, and availability.

Beautiful 1920's Craftsman-Downtown Southern Pines
Kitchen area

Beautiful 1920's Craftsman-Downtown Southern Pines

10.0 out of 10, Exceptional, (54)
"We've stayed here several times. It is a wonderful place to stay when visiting family at Penick. We're able to walk up to visit and also stroll into town for dinner, music, entertainment, etc. This house is a gem! We'll be back."
The price is SAR 507
SAR 1,177 total
includes taxes & fees
3 Dec - 4 Dec
Beautiful 1920's Craftsman-Downtown Southern Pines
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Welcome to Enchanted Escape - a beautiful 1917 bungalow and 2 tiny homes.

Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,

10.0 out of 10, Exceptional, (102)
"Great"
The price is SAR 1,457
SAR 4,116 total
includes taxes & fees
25 Nov - 26 Nov
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Golfers Dream at Pinehurst No. 6 with Pool Table
Spacious Living Room

Golfers Dream at Pinehurst No. 6 with Pool Table

10.0 out of 10, Exceptional, (39)
"Great property clean and great location "
Golfers Dream at Pinehurst No. 6 with Pool Table
Peaceful Southern Pines Home w/ Pool + Yard!
Southern Pines Vacation Rental | 4BR | 3.5BA | 2,560 Sq Ft | Stairs Required

Peaceful Southern Pines Home w/ Pool + Yard!

9.4 out of 10, Exceptional, (30)
"My family and I thoroughly enjoyed our stay here. Pristine, spacious and comfortable. "
Peaceful Southern Pines Home w/ Pool + Yard!
Upstairs at the Estate - Across from SP Golf Club

Upstairs at the Estate - Across from SP Golf Club

9.8 out of 10, Exceptional, (20)
"Great location for this well appointed and super comfortable property!"
The price is SAR 297
SAR 717 total
includes taxes & fees
24 Nov - 25 Nov
Upstairs at the Estate - Across from SP Golf Club
Country retreat home away from the hustle and bustle of city life.
Exterior

Country retreat home away from the hustle and bustle of city life.

9.4 out of 10, Exceptional, (8)
"We stayed here for a wedding nearby. The communication with Bernadette was excellent. We had everything we needed at the house and more. Food lion was a very short drive as well. House was very clean, AC going and set up upon arrival. Neighborhood was quaint and quiet. We would stay again if ever in the area."
The price is SAR 514
SAR 1,182 total
includes taxes & fees
15 Dec - 16 Dec
Country retreat home away from the hustle and bustle of city life.
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
bright and airy open concept living space

The 19th Hole: Sleeps 10. Pool Table, Fire Pit

10.0 out of 10, Exceptional, (21)
"A group of ladies attending golf camp . The property was well worth the money. We enjoyed the peace and quiet neighborhood. "
The price is SAR 845
SAR 1,879 total
includes taxes & fees
24 Nov - 25 Nov
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Idyllic Pinehurst Home, Near Golf Course!
Pinehurst Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,600 Sq Ft

Idyllic Pinehurst Home, Near Golf Course!

9.6 out of 10, Exceptional, (17)
"Nice VRBO. My only suggestion would be a new couch for the living room. "
Idyllic Pinehurst Home, Near Golf Course!
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
Interior

Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!

10.0 out of 10, Exceptional, (18)
"Ideal location with all the extras! If you want to tweak your swing or play another round you can use the simulator. If you are sore or need a recharge, get in the hot tub. Want to have some fun, play on the golden tee or just watch the golfers as they approach the green. Great house!"
Luxury Golf Simulator, Golden Tee, Shuffleboard, Hot Tub and Stunning Views!
New! Epic 12 Bed Golf Vacation - Chipping Inn

New! Epic 12 Bed Golf Vacation - Chipping Inn

2.5 star property
10.0 out of 10, Exceptional, (3)
"Great place and clean as can be"
New! Epic 12 Bed Golf Vacation - Chipping Inn
Lake Escape on Lake Tillery / Gated Community / High Speed Internet
Pool

Lake Escape on Lake Tillery / Gated Community / High Speed Internet

10.0 out of 10, Exceptional, (114)
"Amazing property. So perfectly decorated and it felt like a home away from home. From the cute kitchen to the nice warm fireplace. Can't wait to come back! "
Lake Escape on Lake Tillery / Gated Community / High Speed Internet
Lakefront Tillery Getaway- Pontoon Boat for Rent and Pet Friendly
Welcome to Lakewood Shores!

Lakefront Tillery Getaway- Pontoon Boat for Rent and Pet Friendly

10.0 out of 10, Exceptional, (44)
"Everything was great. Having one key that fit every lock was a convenience that was much appreciated. My girlfriend fell in love with the stray/neighborhood cat would appear whenever there was food present. "
Lakefront Tillery Getaway- Pontoon Boat for Rent and Pet Friendly
1025 Diamondhead: 5 BR, 3 BA House in Pinehurst, Sleeps 12

1025 Diamondhead: 5 BR, 3 BA House in Pinehurst, Sleeps 12

10.0 out of 10, Exceptional, (70)
"Great house would definitely rent again"
1025 Diamondhead: 5 BR, 3 BA House in Pinehurst, Sleeps 12
Gorgeous Pinehurst No 6 Home w/ Two Patios!
Living area

Gorgeous Pinehurst No 6 Home w/ Two Patios!

10.0 out of 10, Exceptional, (24)
"The home was “as advertised “ and we all had a great time!!"
Gorgeous Pinehurst No 6 Home w/ Two Patios!
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Living area

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

9.8 out of 10, Exceptional, (7)
"The house was more than adequate for us. We got more than we expected. Clean, comfortable and located near to the golf courses."
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Palmer House - Pet Friendly

Palmer House - Pet Friendly

9.4 out of 10, Exceptional, (15)
"We enjoyed our stay at the Palmer House this past weekend. It is a comfortable, well laid out, and well equipped house. The shared bathroom toilet is missing a nut to secure the toilet seat. This allowed the seat to slide when used but we were still able to use the unit. The light on the garage door opener was burned out so we swapped it out with a bulb from the light fixture over the dining area table. It seems odd this was the only light switch we could find even though there a fluorescent...
Palmer House - Pet Friendly
The Mulligan!
Game room

The Mulligan!

9.8 out of 10, Exceptional, (14)
"The house was wonderful. It accommodated all of us quite well."
The price is SAR 369
SAR 1,641 total
includes taxes & fees
8 Dec - 9 Dec
The Mulligan!
Lake Tillery- Beautiful sunrises, large screened porch, and newly renovated home
Beautiful Sunrise on Lake Tillery, NC

Lake Tillery- Beautiful sunrises, large screened porch, and newly renovated home

9.8 out of 10, Exceptional, (63)
"it was a great week getaway for relaxing and spent time with the family"
Lake Tillery- Beautiful sunrises, large screened porch, and newly renovated home
Irons & Woods of Pinehurst

Irons & Woods of Pinehurst

10.0 out of 10, Exceptional, (27)
" This place was great for a buddies golf trip. Plenty of space of in a really good and central location. Booking properties managed by a management can always be a gamble, but they were really communicative before the checkin process and made everything very easy. "
Irons & Woods of Pinehurst
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Exterior

Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

10.0 out of 10, Exceptional, (35)
"The house is perfectly located for a Pine Needles, Mid Pines, Southern Pines golf trip. The town of Southern Pines has lots of good dining options just a walk or short drive away. "
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
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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Other property types in Rockingham

Luxurious, peaceful and cozy townhome in the heart of Pinehurst
Spacious Living Room

Luxurious, peaceful and cozy townhome in the heart of Pinehurst

10.0 out of 10, Exceptional, (45)
"We made a last-minute decision to go play golf in Pinehurst and I checked to see if this property was available on the days we wanted, and it was! We stayed here before and loved it so much that we wanted to stay again. It's only 5 minutes to Pinehurst and it's perfect for two. We will be staying again in the future! Thanks again."
Luxurious, peaceful and cozy townhome in the heart of Pinehurst
Golfers Dream at Pinehurst No. 6 with Pool Table
Spacious Living Room

Golfers Dream at Pinehurst No. 6 with Pool Table

10.0 out of 10, Exceptional, (39)
"Great property clean and great location "
Golfers Dream at Pinehurst No. 6 with Pool Table
Large House w/ Private pool - perfect for Golfing Groups (12) beds
Pool

Large House w/ Private pool - perfect for Golfing Groups (12) beds

10.0 out of 10, Exceptional, (68)
"This property is perfectly set-up to handle a large group of family members, groups of families, or a large group of golfers coming to enjoy the great golf options in Pinehurst, like us. We had 12 guys as par of our golfing group. There was plenty of space, beds for everyone, and an unbelievable set of amenities to entertain us when we were not golfing. From the pool, to the pool table, ping pong, arcade games, and the large family room with a big screen tv, this house had it all. The...
Large House w/ Private pool - perfect for Golfing Groups (12) beds
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.