
Holiday houses in Windsor Park
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Top-rated holiday rentals in Windsor Park
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Miss Nancy's Place
Come enjoy your stay in this charming Centry plus old home located in the beautiful Historic District of Cheraw. Come see why this town was labeled "the prettiest place in Dixie" by General Sherman during his occupation of Cheraw in 1865. The front porch with rockers and a porch swing are a guest favorite. Quiet neighborhood where neighbors greet you with a wave as they walk their dogs. Centrally located within walking distance to downtown and locally owned restaurants, antique stores, gym, ect

Gorgeous Southern Home in Cheraw
Planning your next family reunion or friendly getaway? This beautiful and historic 5,354 sq. ft. 5-bedroom, 3.5-bath Cheraw vacation rental is the one for you. Featuring 5 living areas, a fully equipped kitchen, and a private fenced in yard, this lovely abode offers plenty of space for your group to spread out and feel at home. Be sure to pack your hiking boots or golf shoes and explore Cheraw State Park. Spend your evenings playing board games in front of any fireplace or enjoy the fire pit.

Tiny Guest House By Fishing Pond
Enjoy the sounds of nature when you stay in this unique place. Country setting, but close enough to a lot of activities. Close to Charlotte and Charlotte motor Speedway. Wineries, PNC pavilion. Great Wolf Lodge and Concord mills. Enjoy visiting the goats and chickens. They love animal crackers and you’ll find some by the gate to give them. We are earth friendly using plant based cleaning products. We have waterless dry toilet. We are a working farm and offer farm fresh eggs when available.

Cozy hunt box on 220 acre farm.
Cozy 2 b 1 b apartment. Split floor plan w/ familyroom/kitchen combo. Kitchen has small fridge, microwave, Keurig, dishes & utensils. Bathroom has a custom vessel sink & tile shower w/ rain water head. Everyone raves about the shower! Pets are welcome. Dog training space w/ a pond and 1 pasture maybe available for horses at an additional cost. (all animals must be UTD on shots & horses must have neg Coggins). We are located close to H Copper Black, Chesterfield, Cheraw & Hartsville.

Historic one bedroom apartment in Chesterfield
Just one block from the Chesterfield County Courthouse and Main St., walking distance to several bars and restaurants. This unit has a colonial Charleston vibe with a queen size rice bed set. The living room is furnished Victorian with smart tv (wi-fi), and the full bath and kitchen are black and white reminiscent of 1920. Both kitchen and bath have new fixtures and appliances. Totally refurbished in 2022, with tall ceilings and hardwood floors. Washer and Dryer access available.

Burchs Carriage House
Private carriage house sitting adjacent to the most historic estate home in the lovely town of Society Hill. Separate entrance for guests which accommodates large horse trailers. Property caters to all animals! Kitchenette (microwave, toaster oven and hot plate), washer/dryer, Apple TV and wifi. Continental breakfast, wine/snacks provided. BBQ grill also. 2 stalls with paddocks. 12 x 12 and 10 x 12. Rooms are as they would be at your own home, separate from each other. See photo 13.

The Cottage at Dream Acres & Petting Zoo I-95/I-20
The Cottage at Dream Acres is situated with its own private drive on our 8 acre working horse farm located near Florence SC at the I-20/ I-95 corridor, 5 mins off the highway. We are the 1/2 way point between NY & FL. Relax and unwind from a long roadtrip or take a weekend farm-stay getaway. All the amenities of a larger home with the convenience of a smaller space! Family Friendly; sleeps up to 4, newly renovated in 2020, petting zoo, outdoor fire pit, tree swing, picnic table!

Tranquil Dirt Road Living
Take it easy at this unique and tranquil getaway. We are located in a country setting away from the hustle and bustle of busy life. It is located near the headquarters of H Cooper Black Preseve where dogs and horses abound; Near Moree Sportsman Preserve,Camp Coker and Cheraw State Park where you can enjoy watersports, golf, and other outdoor fun. Whether you come for the sporting or relaxation you can rest your head here at our tranquil and comfortable retreat amongst the pines.

A-Frame of Mind & 30 min from city
Unplug and unwind at our beautifully renovated A-frame cabin, tucked away in the peaceful Mint Hill area—just 30 minutes from the city. Surrounded by nature, this one-of-a-kind getaway offers the perfect blend of rustic charm and modern comfort. Enjoy fresh air, cozy fires, and starry nights in a peaceful, nature-filled setting. Whether you're looking for a romantic weekend, a quiet family escape, or just a break from the everyday, this tranquil retreat is ready to welcome you.

Farm Cottage in Laurinburg
Cozy farm house right on the edge of town. This 2 king bedroom home offers ensuite bathrooms, and a full open living and kitchen space. Enjoy the peace & quiet of The Gilchrist Farm with the convenience of being close to local amenities. Front porch rocking chairs and a backyard firepit invite you to relax at sunset. Dog friendly home. Only 2.5 miles to Downtown, 3.5 miles to central dining/shopping (Starbucks, Walmart, etc.), 5 miles to Scotia Village.

Lloyd’s Country Cottage - Cheraw
Looking for a country retreat? THIS IS IT! Conveniently located between Cheraw and Chesterfield. Ample yard for recreational vehicles/trailers. Fiber optic high speed internet, perfect for remote workers. Close to many area attractions! Cheraw State Park, H. Cooper Black, Great PeeDee River, Moree’s Hunting Preserve, Darlington Speedway, Club MX, Hartsville Water Park, Camp Coker and Lake Robinson. We are thrilled to share our home with you!

Enchanting Treehouse with Modern Amenities
Perched on 20 acres along Catfish Creek, this enchanting tree house allows you to appreciate nature from a birds eye view. Whether it’s kayaking, canoeing, or exploring along the creek; relaxing in the hammocks and swings; engaging in a board game; or roasting marshmallows at the fire pit, Amenities include a full kitchen with full bath, outdoor shower, booth seating in dining table for up to 8, 2 bunk beds and loft style sleeping.
Popular amenities for Windsor Park holiday rentals
Other great holiday rentals in Windsor Park

Little Cottage on Tillery

Spacious 3 bd Home with Office, GameRoom & Balcony

Clean Cozy Cottage near I-20 & I-95

'Cardinals Retreat'

The Pinecone Retreat - Only 1 mile from i95

Ted's Place, R'ham's Premiere Home away from Home!

The 19th Hole– Your Pinehurst Golf Getaway Awaits!

Lu's Hideaway @ Lakeshore Haven
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