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Jamestown Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Jamestown vacation rentals

Exterior
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit
4.0 star property
Winston-Salem
8.0 out of 10, Very Good, (1)
"House was clean and amenities were good. House is in a great location. Be aware that there is another rental unit downstairs that may have other parties occuppying."
United States
Elizabeth
The price is ￥19,518
￥45,541 total
includes taxes & fees
Jan 14 - Jan 15, 2026
King Beds Hot Tub Arcade Grill & Firepit
In-room dining
Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade
4.0 star property
Winston-Salem
8.0 out of 10, Very Good, (1)
"The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt...
United States
Rami
The price is ￥24,733
￥48,005 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Heated Pool King Bed Jacuzzi Bath Arcade
BBQ/picnic area
Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry

Exec Suite King Bed Hot Tub Gym Laundry
4.0 star property
Kernersville
The price is ￥29,879
￥45,474 total
includes taxes & fees
Dec 28 - Dec 29
Exec Suite King Bed Hot Tub Gym Laundry
House (3 Bedrooms) | Interior
Bright & Elegant Home in High Point w/ Deck!

Bright & Elegant Home in High Point w/ Deck!

Bright & Elegant Home in High Point w/ Deck!
3.0 star property
High Point
The price is ￥19,049
￥65,854 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Bright & Elegant Home in High Point w/ Deck!
Fridge, microwave, oven, stovetop
Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub
3.5 star property
Winston-Salem
The price is ￥27,243
￥69,927 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Arcade Kid Friendly Firepit Grill HotTub
Exterior
The Ardmore Executive Suite

The Ardmore Executive Suite

The Ardmore Executive Suite
3.5 star property
Winston-Salem
6.0 out of 10, (3)
"Very clean and nice setup "
United States
Nicholas
The price is ￥25,646
￥40,723 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Ardmore Executive Suite
Children's activities
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
3.0 star property
Kernersville
6.0 out of 10, (4)
"The house was very nice. Very well kept up. Enjoyed the atmosphere. Hope to stay there again. Great experience. 😃"
United States
Troy
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee
House | Terrace/patio
Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub
3.5 star property
Winston-Salem
The price is ￥23,608
￥65,558 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Winston Sleeps 16 - 2 Kitchens Hot Tub
Seasonal outdoor pool, pool umbrellas, sun loungers
KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic

KingBed Hot Tub BBQ Games Hypoallergenic
3.5 star property
Kernersville
4.8 out of 10, (3)
"We ended up not staying because after i booked they listed all the fees. You have to check in by 8 pm but is listed as 2:30am and there is a $20 per person per day fee to use the pool. And you have to give a 48 hr notice to even use the pool and i booked last minute so that would have been a waste too. To use the hot tub its $100 extra but that is the only thing listed before you book. It would not have been worth the 3.5 hr drive we were going to make. "
United States
Tiffany
The price is ￥19,792
￥34,077 total
includes taxes & fees
Dec 28 - Dec 29
KingBed Hot Tub BBQ Games Hypoallergenic
House (3 Bedrooms) | Interior
Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is ￥24,826
￥71,015 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Cottage: Nature-filled Winston-salem Retreat!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jamestown Hotel Reviews

Proximity Hotel

Proximity Hotel

10/10 Excellent
"Room was spotless and staff was amazing. We'll definitely stay there again!"
Claude 2-night trip
Posted 19 hours ago
Proximity Hotel

Find out more about Jamestown

Search for holiday rentals in Jamestown on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamestown using one of the methods below:

  • View our selection of featured holiday rentals in Jamestown
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  • Enter your travel dates to view the best deals on holiday rentals in Jamestown while they last

Look no further and take a look at our great range of rental properties in Jamestown!

Frequently asked questions

Can I find vacation rentals in Jamestown?

Yes, there are vacation rentals in Jamestown close to High Point City Lake Park, or you can go with a more secluded option if you're looking for extra privacy while you relax. Jamestown is known for its shopping and restaurants.

What are some of the best vacation home rentals that Jamestown has to offer?

Theater, heated pool/hot tub near HPU/Market: Visitors give good reviews to this Jamestown vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub. Another good choice for your trip to Jamestown is Arlington Oasis | Sport Court, HotTub, Golf, Games.

How many vacation rentals are there in Jamestown?

With 22 Expedia vacation rentals, you're sure to find just the right place for your Jamestown stay.

What’s there to see and do in Jamestown?

While exploring the area, visit family-friendly sights like High Point City Lake Park, or get outside and enjoy nature at Guilford Courthouse National Military Park. Other places in town to visit include Castle McCulloch and World's Largest Highboy Dresser.

What’s a vacation rental in Jamestown like?

Vacation rentals are privately owned properties you can book for a long or short time in Jamestown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.