Holiday rentals in Jamestown

4.95 out of 5 average rating, 145 reviews

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.

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An aerial view of the property reveals a spacious two-family home with a well-maintained lawn and landscaped area. A wooden staircase leads to The Sky Deck, while the serene lake is visible in the background, surrounded by trees.

4.98 out of 5 average rating, 120 reviews

2 bed/2 bath with LR, DR, Kitchen, Laundry & Deck

Enter from The Sky Deck, a 3 story high deck. 2 bed, 2 bath, 1000 square ft space with full kitchen, living room, dining room & laundry. All new furnishings/appliances. No shared space. Complete privacy. Professionally decorated. Newly added lighted makeup mirrors and full length mirrors in each bathroom/bedroom. Stone patio on lake. 5 miles to Furniture Market and High Point Hospital. 10 miles to Greensboro Coliseum! Built in 2019 above my home. Parties/additional guests are not allowed.

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A welcoming front porch features a custom daybed swing adorned with black and white cushions. Lush greenery is visible along the edges, while a doormat reading 'You're Exactly Where You Need to Be' adds a personal touch. Lanterns and potted plants complete the inviting space.

4.97 out of 5 average rating, 230 reviews

<5min to HPU & Market *The Historic Escape*

We are 𝐉𝐨𝐡𝐧𝐬𝐭𝐨𝐧 𝐄𝐬𝐜𝐚𝐩𝐞𝐬 and we welcome you to 𝐓𝐡𝐞 𝐇𝐢𝐬𝐭𝐨𝐫𝐢𝐜 𝐄𝐬𝐜𝐚𝐩𝐞! Originally The "Louis Johnson Diffee House", located in the popular historic district! 3 BR, 2.5 bath & 3 porches, with the front porch offering a custom daybed swing! Conveniently located and walking distance to many restaurants such as Sweet Old Bills BBQ, Christina Gray’s, & an award winning craft brewery, Brown Truck Brewery! Mins to HPU, HP Market, and the new Rockers Baseball Stadium!

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Guest suite in Greensboro

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.

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4.97 out of 5 average rating, 189 reviews

4.97 out of 5 average rating, 95 reviews

An outdoor fire pit is surrounded by several Adirondack chairs, set against the backdrop of a modern Scandinavian home. The structure features large windows and a spacious deck, illuminated by soft lighting under a dusk sky, with lush trees framing the scene.

Home in Greensboro

Poplar House

Enjoy a stylish experience at this centrally-located home. Minutes to everything in Greensboro, High Point and Jamestown. Located in the prestigious Sedgefield Community. This is a modern Scandinavian new-build with all the vibes. This home has 4 bedrooms & a small private nursery. A fully stocked kitchen for you and your crew, cozy hang out spaces indoors and out. Relax in a private back yard with a fire pit or enjoy a moment with friends and family on one of multiple decks.

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A single-story ranch house with a welcoming front porch. Surrounding greenery includes mature trees and well-maintained shrubs. A spacious lawn is visible, providing a serene outdoor environment. A car is parked in the driveway, indicating easy access to the home.

4.98 out of 5 average rating, 225 reviews

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.

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4.96 out of 5 average rating, 197 reviews

A cozy living area is highlighted by a light-toned sofa and a decorative coffee table, both featuring neutral accessories. A charming lamp stands near the seating, and a small holiday display is presented on the table, adding a festive touch to the organized space.

Cottage in Jamestown

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.

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4.92 out of 5 average rating, 360 reviews

Guest house in Jamestown

Beautiful Duplex

PLEASE READ BEFORE BOOKING Maximum Occupancy: 2 GUESTS (Including Children) check in is at 3:00 PM. Check out at 10:00 AM. Enjoy a simple, peaceful stay in our centrally located duplex . 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.

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4.95 out of 5 average rating, 110 reviews

The living area features large, arched windows allowing abundant natural light, complemented by a cozy sectional sofa arranged around a central coffee table. A flat-screen TV is mounted above the fireplace. A staircase leads to the upper level, visible in the background.

Home in Greensboro

7 BR on PGA Tour’s Sedgefield CC range Hot Tub

3 story, 7 BR house 250 yards from Sedegefield’s clubhouse overlooking the historic driving range. 2020 kitchen renovation. 2021 back deck expansion with brand new hot tub cleaned after each guest. Modern house complete with pool table, ping pong table, & game room. Your kids will love it. Master bathroom has jacuzzi tub. Twin over Full bunks in two rooms means there are 10 beds for use. 5 car limit. Additional parking available nearby upon request.

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A charming Craftsman home, built in 1928, is surrounded by a lush lawn and mature trees. The front porch, adorned with a welcoming heart decoration, features white railings and overlooks vibrant shrubs. An American flag stands proudly in the front yard, enhancing the tranquil setting.

4.92 out of 5 average rating, 239 reviews

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.

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4.99 out of 5 average rating, 169 reviews

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.

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The exterior of the home features a two-story brick façade, complemented by a well-manicured lawn and colorful flower beds. A flag is displayed on the front porch, while a driveway leads to a spacious garage. Trees provide a natural backdrop to the property.

4.82 out of 5 average rating, 101 reviews

Cheerful 4 bedroom home in quiet neighborhood.

Come stay in this charming home located in desirable Jamestown. Why get a hotel when you can enjoy the space, comfort, and amenities of a home? There is a bedroom and full bathroom located on the main level. Relax on the back patio by the fire pit, or grill out on the gas grill. This home is Walking distance to downtown Jamestown shopping and dining.

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Popular amenities for Jamestown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Jamestown

4.94 out of 5 average rating, 63 reviews

Townhouse in Greensboro

Bridford & Co.

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Superhost

A charming two-story home is presented with a spacious front porch supported by white columns. Well-maintained landscaping features shrubs and flowers, creating an inviting entry. The driveway leads to a two-car garage on the side, and lush green grass enhances the overall appeal of the property.

4.7 out of 5 average rating, 61 reviews

spacious | gatherings | 5 bdrm | whole house

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5.0 out of 5 average rating, 24 reviews

Quiet, Open, King bed, w/on suite Close 2 HPU & FM

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4.94 out of 5 average rating, 16 reviews

The Tour-it House/2 bed walk to downtown/greenway

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Superhost

An overhead view captures the spacious outdoor area featuring a heated pool, surrounded by lounge chairs. A stone fire-pit is positioned in the corner, while the large lawn area offers ample space for outdoor activities. The house, with a well-defined layout, complements the inviting landscape.

4.74 out of 5 average rating, 70 reviews

Hot tub | Fire-pit | Pool Table | Heated Pool

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4.94 out of 5 average rating, 53 reviews

Tranquil Jamestown culdesac home

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5.0 out of 5 average rating, 5 reviews

The dream tiny house

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