Family-friendly holiday rentals in Jamestown

Spacious 7BR Home for 21 Guests

Escape to our fully renovated 7-bed, 4.5-bath Jamestown retreat, perfect for up to 21 guests. Ideal for large families, groups, and corporate stays, sports groups, this spacious home features a game room, screened porch with ping-pong, and a chef’s kitchen on a private half-acre lot. Walk to downtown Jamestown restaurants, bakery, brewery, nightlife, and shopping. 7 mi to HP Market, 4 mi to Sedgefield CC, 10 mi to GSO Coliseum/Aquatic Center, 5 mi to HPU, 10 mi to UNCG, and 12 mi to PTI Airport.

Clean, comfy, walk to downtown

Your visit to Jamestown will be comfortable in a clean, well-stocked home. Just a walk to Jamestown and its restaurants, entertainment and stores. Enjoy the large, dog-friendly fenced yard and covered patio with outdoor seating and grill. All important amenities are included, such as, coffee/tea station, laundry and strong WIFI. The home is surrounded by family neighborhoods (quiet hours 11pm-7am) and trail heads for strolls or hiking. Easy drive to Greensboro, HighPoint, Winston and Asheboro.

Stylish Hamilton Lakes Loft w/Terrace & Park View

Private 2-level Mid-Century style loft in quiet and prestigious family neighborhood w/separate entrance & large private terrace overlooking parkland. The Loft is at one end of our MCM ranch. Upstairs Loft sleeps 3. Large lower level includes living & dining area, 55" smart TV, microwave, mini fridge, toaster oven, coffee bar, and full bath w/walk-in shower. Three miles of trails start across the street; 5-minute walk to Lake Hamilton. Third & 4th guests (must be under 18) are $30 each per night.

Arya’s cottage with a loft & jacuzzi

Adults only, 18&older. No smoking or vaping allowed inside or on premises. Up to 2 dogs welcome for an additional fee. Peaceful cottage, centrally-located on an active equestrian farm with rv sites as well. From your loft bedroom overlook beautiful rolling pastures with horses and goats. See our beautiful horses in training or take a stroll on our walking trails or through the woods on the 41 acres, read a book, sit around your fire pit, soak in the private jacuzzi, or head 6 miles to downtown.

Sunset Hills Carriage House! King Bed

Industrial Chić Abode in Beautiful Sunset Hills! Close to Everything with all the comforts of home. The Carriage House offers a private self contained guesthouse located behind our house ( 485 sq ft studio ) Safe upscale neighboorhood. Comfy King Bed! We have a pullout Queen sofa bed available for extra guests! 2 car max, NO SMOKING OR PETS! Walkable to UNCG and 2 minutes from everywhere you want to be! Close to Lindley Park favorites at the corner, UNCG, Downtown and Greensboro Coliseum.

Tree Haven

Escape to a peaceful, wooded retreat in this unique 2 bedroom/1 bath space nested under the hosts’ residence in Greensboro, NC. Enjoy a private driveway and entrance, and a covered porch with a swing. Ideal for work or play, the space features fast internet, a smart TV, a well appointed kitchenette, custom woodwork for a modern rustic feel, and a backyard with a fire pit for relaxing evenings. This tranquil hideaway offers space, comfort, and privacy in a quiet residential neighborhood.

Pet-Friendly High Point Stay with Fenced Backyard!

Perfect for couples, small families, business travelers, and HPU visitors, Emeryview II offers comfort, convenience, and a prime High Point location. Our cozy 2-bedroom, 1-bath home features a fully equipped kitchen, comfortable living area, fast WiFi, driveway parking for 2 cars, and a fenced backyard. Whether you're visiting High Point University, attending Furniture Market, or exploring the Triad, you'll enjoy easy access to downtown High Point and the area's top destinations.

Jamestown Cottage

Great location, immaculately clean, and tastefully decorated in a natural, light pallet. I would call it a romantic cottage. The back yard offers privacy, fire pit, and water feature. Walk to Jamestown's trendy restaurants and downtown entertainment. Adjacent to 33 acres of undeveloped land that delivers nature's serenity. Rest well on the luxury hybrid mattress. Well stocked kitchen with many accessories. High speed fiber optic wi-fi. Best suited for a couple, or 2 guests.

Stylish Comfy Home Centrally Located to Triad Area

This is a great place for your next getaway. Whether you’re in town for a family reunion, visiting a child @college, a business group, or wedding , this home is a great place to stay! Great stylish place! You’ll love this space with it's four bedrooms. One of which is perfect for children but can accommodate one/two adults as well. The house is located in a quiet neighborhood close to great restaurants, shopping, Greensboro and Winston Salem. Perfect for your next trip.

Gorgeous tiny house .

PLEASE READ BEFORE BOOKING Maximum Occupancy: 2 GUESTS (Including Children) check in is at 4:00 PM. Check out at 11:00 AM. Enjoy a simple, peaceful stay in our centrally located tiny house. We're just 15 minutes from UNC Greensboro, High Point University, the Greensboro Coliseum, Four Seasons Mall, Friendly Center, Piedmont Triad International Airport (GSO) and both Downtown Greensboro and High Point. Downtown Jamestown and Greensboro topgolf only 5 minutes away.

A Suite Get-A-Way Your Home Away from Home

LOCATION-LOCATION-LOCATION Located in Greensboro at Jamestown/Sedgefield Very convenient to High Point/Furniture Market, Winston-Salem, Burlington & all Piedmont Triad area venues and 18 Universities & Colleges. Only minutes to: Interstates: I-85, I-40, I-73, I-74, I-785, I-840, and Highways: 421, 29, 70, 220, 311. Comfortable guest suite/apartment with 600+ sq. feet of living space, private entrance, patio, and parking A perfect home away from home!

2-BR, 1-Bath Unit with Game Room & Free Parking

Fully furnished 2BR, 1BA completely private basement unit featuring a cozy living area, game room with pool table, darts, and Xbox, plus a backyard firepit. Includes 2 dedicated parking spaces. Amenities: Smart TV & Netflix Coffee machine, microwave, toaster & air fryer Mini fridge, music system, iron & ironing board Note: Please note that this unit does not include a kitchen. Note: It is Complete Private Unit with a separate entrance and Exit.