Family-friendly holiday rentals in Jamestown

The Woodfern House | 7BR, 4.5BA | Sleeps 21

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.

Indoor spaces · Family · Check-in

Charming Newly Renovated Starmount Forest Home

Starmount Forest is a quiet upscale neighborhood in the heart of Greensboro. Located just half a mile from upscale dinning and shopping In Friendly Center. This Spacious 2300 sq ft home features an inviting open floor plan with a large kitchen, den, living room and sunroom. The Kitchen is fully equipped with stainless appliance and everything you need to cook your favorite meal. New Furnishings throughout, master bath boasts large walk in shower, and every bedroom is equipped with a smart TV.

Family · Kitchen · Laundry

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.

Indoor spaces · Family · Wi-Fi

Downtown Jamestown, quiet, clean and spacious!

Location is key! A block from quaint Jamestown's food and entertainment 5 miles from Furniture Market, 4 miles from HPU, 8 miles from downtown Greensboro or coliseum area and less than 20 miles from Winston. Adorable ranch, recently updated and has all the comforts of home. Pet friendly with fully fenced backyard. Both business travelers and families will enjoy the safe , quiet neighborhood. It is walking distance to dining, coffee shop, bakery, entertainment, parks and trails.

Family · Kitchen · Checkout

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.

Indoor spaces · Family · Layout

Westbury Wonderful - Your cozy home away from home

Relax with the whole family at this cozy, peaceful place to stay. This 3 BR / 2 BA home offers a comfortable, quiet place to stay during your visit to the Greensboro area. Minutes away from restaurants, shopping, event venues and world-class golf, Westbury Wonderful is sure to be your home away from home! Proximity: High Point University: 4 miles UNCG: 11 miles Coliseum: 11 miles Wesley Long Hospital: 13 miles Greensboro Airport: 14 miles NC A&T: 16 miles NC Zoo: 30 miles

Family · Indoor spaces · Access

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.

Indoor spaces · Family · Wi-Fi

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.

Kitchen · Family · Sleep quality

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.

Family · Indoor spaces · Hospitality

Like living in the country, but right in town...

Your family will be close to everything when you stay at this centrally-located place. Downtown and High Point University are only a 5 minute drive. Newly refurbished Craftsman home dates back to 1928, with all new kitchen appliances, washer/dryer, and new HVAC system. Home sits on a nice wooded 1.5 acre lot, away from the road. All the comforts of home - plus a wonderful front porch to relax on and enjoy the scenery.

Kitchen · Indoor spaces · Quiet

Madison Suite

This newly renovated house is nestled in the middle of High Point. You can walk to restaurants, bars, shopping, and other attractions including the ballpark, children's museum, farmers market, and more! 5 min walk to Sweet Old Bills, 83 Custom Shop, Brown Truck brewery, Monkee’s and Wynnie’s boutiques, and many other shops and restaurants! This special place is close to everything, making it easy to plan your visit.

Indoor spaces · Family · Laundry

Bright High Point Home | Lake Access | BBQ

Spacious 𝗛𝗶𝗴𝗵 𝗣𝗼𝗶𝗻𝘁, 𝗡𝗖 retreat conveniently located near High Point University and the Furniture Market. Perfect for families, groups, and pets, featuring a fenced yard, cozy fire pit, two Smart TV dens, and a fully equipped kitchen. Enjoy a comfortable, convenient stay with everything you need to relax and make lasting memories. ☀ Fast Wi-Fi ☀ BBQ Grill ☀ Lake Access ☀ Patio

Kitchen · Family · Hospitality