Holiday rentals with a fireplace in Richmond County

"Perched in Pinehurst"

Planning a visit to beautiful Pinehurst, NC? Welcome to Perched in Pinehurst, a cozy and thoughtfully appointed first-floor condo located less than half a mile from the iconic Pinehurst Resort. Perfectly situated between Golf Course #5 and the Harness Track, this charming retreat offers convenience and peaceful surroundings. Attending an event at The Fair Barn? You’re directly across the street — no driving required. Golf, shops, restaurants, and village attractions are all just minutes away.

The Tee and Tea House

The Tee & Tea House is a golfer’s retreat just 3 miles from Pinehurst Resort, Pinehurst No. 2, and the Historic Village. Spacious on two levels, it features a golf-viewing den upstairs and a large, open entertainment area downstairs ideal for gathering, watching golf, playing cards or preparing meals with dining seats for 10. Owners from the UK provide premium teas and coffees for a unique morning ritual. A two-car garage makes it easy to store clubs, clean shoes, and prep for early tee times.

Near Pinehurst Resort | Golf Retreat | Pool Table

Looking for a quiet golf getaway near Pinehurst without the crowds? This serene Jackson Springs retreat offers the best of both worlds—privacy, nature, and easy access to the Sandhills’ top destinations. Tucked beneath mature longleaf pines on a quiet street, this 3-bedroom, 2.5-bath home backs up to a former golf course (now a peaceful walking path) creating a calm, nature-filled backdrop you’ll feel the moment you arrive. Mornings here start with coffee on the deck and the sound of birds.

A Cozy Retreat on No. 5

Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.

Caddy Shack #2 Golfers come back year after year!

Caddy Shack #2 is a great vacation experience for groups of up to 12. Enjoy free Wifi, play Ping Pong, Shuffleboard, Arcade (130 classic games including 29 Golden Tee Courses), Foosball and Custom Corn Hole. The fully equipped cottage is centrally located in the quiet Village 2 miles from historic Pinehurst #2, pubs, dining and entertainment and within minutes to 30+ championship golf courses. To accommodate your group up to 24 guests, check out our adjacent house - Caddy Shack 1.

The Porch House

Escape to this peaceful, fully-furnished home nestled in a quiet, family-friendly neighborhood surrounded by towering pine trees and ample shade. Perfectly located near premier golf courses, scenic outdoor trails, neighborhood playground, recreation area with a lake, and the iconic Rockingham Speedway. Unwind on the inviting porch, perfect for morning coffee or explore the local area with all it has to offer. This home offers the ideal blend of relaxation and adventure.

The Pinehurst Paradise Pool Home

Your family will be close to everything when you stay at this centrally-located home. Only minutes from the Pinehurst Resort & C.C. and village! I have been told my home is happy, fun, cozy, homey yet very clean and accommodating. Enjoy swimming in the pool, chipping golf balls on to the floating green, playing corn hole, and watching the outdoor TV while grilling out or lounging in a pool float! There is a covered gazebo with curtains and a gas fire pit.

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay & Play Retreat! Completely renovated for ultimate comfort, this modern home is the perfect base for your next adventure. You are just 8 miles from iconic Pinehurst No. 2, 10 miles from the Carolina Horse Park, 14 miles from Rockingham Dragway, and 16 miles from Fort Liberty. Enjoy world-class golf and endless dining options all within a 10-mile radius of this stylish getaway. As you can tell from our reviews, you won't be disappointed!

Captain’s Choice

With full renovations completed in 2023, our condo is centrally located and only steps away from the golf course(s) and just across the street from the Pinehurst Harness Track and Fair Barn. Take a leisurely stroll to the Pinehurst Resort, the Village and the Village Green for unique shopping, dining and entertainment. And finally, the charming communities of Southern Pines and Aberdeen are only a few miles away and are worth exploring!

Pinehurst No. 1 - Secluded golf front retreat

One of a kind private golf front home on Pinehurst course #1 with no adjacent neighbors and incredible golf views. The property is located on the end of it's own street and is the perfect location for a golf getaway. Just minutes to Pinehurst Resort, Mid-Pines, Pine Needles and other great golf courses in the area. Enjoy local fine dining, pubs, shopping, and galleries nearby in the Village of Pinehurst or Southern Pines.

Sarah's House

Kick back and relax in this calm, stylish space. Close proximity to major restaurants, stores, highways 73/74, US Route 1 and 220. Perfect location for Rockingham Motor and Drag Speedways. Whole house, comfort for the entire family. Brand new home renovation and furnishings. A gem and rare find for transient or long-term guests. You will absolutely love this place.

The Suite Spot

This centrally located suite is the perfect spot for your next visit to Pinehurst. Come and enjoy the views from the back covered porch, book a tee time at one of Pinehurst’s world renowned golf courses, soak up some North Carolinian vitamin D and then take a dip in the pool, or simply stay indoors and let The Suite Spot be your sweet respite from the world.