Holiday rentals with a fireplace in Richmond County

Hot Tub * King Bed * Putting Green * Amazing Golf

Welcome to The Stay and Play Retreat! We’re centrally located minutes away from some of the areas greatest attractions such as Pinehurst No. 2 (8 Miles), Rockingham Dragway (14 miles), Carolina Horse Park (10 miles), and Fort Bragg (16 miles) . We're also surrounded by many beautiful golf courses including Pinehurst & Legacy Golf Links. A wide variety of dining options within 11 miles of this completely renovated home that has been created specifically for your comfort, relaxation & enjoyment.

"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.

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.

The Ultimate Golf Trip House - Pool & Pickleball

Escape to Foxfire in the Pinehurst area and enjoy a luxury lakefront estate built for large groups and unforgettable stays. With a pool, hot tub, sauna, cold plunge, golf simulator, game room, pickleball/basketball court, and 2 full kitchens, there’s something for everyone. Sleeping up to 24 guests across 12 beds, this retreat also features a private dock, putting greens, fire pit, outdoor pizza oven, and multiple decks overlooking the lake—perfect for relaxing and making memories.

Pinehurst Golf Retreat | Near Cradle & Resort

Breathe in the calm of Pinehurst at this updated 3BD/2BA condo beside Course No. 5 — just minutes from the Pinehurst Village, Pinehurst Fair Barn and world-class golf. Perfect for families and golf groups alike! Enjoy a fully stocked kitchen, cozy living space with a basket of games, and thoughtful family touches like a high chair and pack ’n play. Spend your days exploring the greens, shopping in the Village and watch the sunset through the pines from your private patio.

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.

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!

Best Golf Trip Rental in Pinehurst

Location!! Walk to Resort /Cradle/ Thistle Du. Updated Everything! New Beds, New Sheets, New Furniture, New Bathrooms, 2 new 70 inch Smart TVs, Fire Fit, Pool Table, Grill, Card Table, Great Views of the 16 green/17th Tee on #1 course. Close to CCNC/ Mid Pines/ Pine Needles/ Forrest Creek. This Cottage offers everything you want in a Pinehurst Golf Trip. FOLLOW: @longleafcottage on IG **no RVS or Trailers allowed**

Par In The Pines

Forget your worries in this spacious and serene space. Completely remodeled and waiting for you to come and enjoy. This unit offers 2 large decks for enjoying the scenery overlooking the Foxfire golf course. Only 6.8 miles to the Pinehurst Clubhouse and Pinehurst Village. Come and enjoy amazing golf courses, shopping, restaurants and all the historic Sandhills area has to offer.

Super comfy and cozy, one bedroom studio.

Our little oasis has everything you need - your own private entrance, a super comfortable, king-size bed, the biggest, most luxurious shower you've ever seen, and a kitchenette that includes a mini-fridge, a microwave, and a combination toaster oven, air fryer, and a coffee maker. We are confident that you will not be able to find a better stay anywhere in the area.

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.