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Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

Theater, heated pool/hot tub near HPU/Market

2.0 star property
8.0 out of 10, Very good, (3)
"very clean and property owners very responsive and helpful… enjoyed my stay thank you"
The price is NZ$584
includes taxes & fees
28 Sept - 29 Sept
Theater, heated pool/hot tub near HPU/Market

Arlington Oasis | Sport Court, HotTub, Golf, Games

9.6 out of 10, Exceptional, (7)
"House was perfect for our group size and allowed my co-workers to connect. Plenty of room for everyone. "
Arlington Oasis | Sport Court, HotTub, Golf, Games

InTown Suites Extended Stay Greensboro NC - Airport

2.0 star property
6.2 out of 10, (665)
"Front desk was handled very beautifully."
InTown Suites Extended Stay Greensboro NC - Airport

⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

9.8 out of 10, Exceptional, (61)
"Home was clean, great location. "
The price is NZ$545
includes taxes & fees
9 Oct - 10 Oct
⭐️ Amelia’s Retreat ⭐️ @ Greensboro 🐕🏥🏙🏊‍♀️🛍🍔🥂 Close

The Hot Tub Hideaway

9.6 out of 10, Exceptional, (24)
"Stay is awesome!"
The price is NZ$464
includes taxes & fees
28 Sept - 29 Sept
The Hot Tub Hideaway

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

3.0 star property
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. 😃"
Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Family Fun Home 2 Bedroom 1 Bathroom close to Downtown Greensboro

10.0 out of 10, Exceptional, (15)
"Had a nice stay, and I like how much they've tried to cater to the family element, LOTs of entertainment options. Only suggestion is that they might want to get someone to read over their literature. "
The price is NZ$547
includes taxes & fees
30 Sept - 1 Oct
Family Fun Home 2 Bedroom 1 Bathroom close to Downtown Greensboro

King Beds Hot Tub Arcade Grill & Firepit

4.0 star property
The price is NZ$462
includes taxes & fees
14 Oct - 15 Oct
King Beds Hot Tub Arcade Grill & Firepit

Cozy 2-bedroom bungalow in lovely Winston-Salem

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay and loved the house. Great location for our needs."
The price is NZ$451
includes taxes & fees
1 Oct - 2 Oct
Cozy 2-bedroom bungalow in lovely Winston-Salem

The Cabin - Fire Pit, Pool Table, Spacious

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great house in perfect location!"
The price is NZ$1,083
includes taxes & fees
29 Sept - 30 Sept
The Cabin - Fire Pit, Pool Table, Spacious

Discover "RusticParaiso": Spacious Elegance and Serene Urban Countryside Retreat

10.0 out of 10, Exceptional, (20)
"Wonderful home, great host!"
The price is NZ$2,099
includes taxes & fees
29 Sept - 30 Sept
Discover "RusticParaiso": Spacious Elegance and Serene Urban Countryside Retreat

Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

10.0 out of 10, Exceptional, (47)
"Lovely space... super clean and cozy, close to everything in Winston-Salem but secluded enough. We will be definitely staying here again when we come back next year."
The price is NZ$408
includes taxes & fees
7 Oct - 8 Oct
Cozy King Blue H2O Staycation , Stock Tank Pool, Hot Tub, Fire Pit Pets OK!

Walden Cabin Experience

10.0 out of 10, Exceptional, (24)
"Wonderful family, memorable visit.Highly recommend "
The price is NZ$219
includes taxes & fees
28 Sept - 29 Sept
Walden Cabin Experience

NEWLY RENOVATED- Long Term Stay.

2.0 out of 10, (3)
"very dirty. If you have allergies or asthmatic do not stay there you will die smell cigarettes everywhere people are smoking all over the place."
The price is NZ$180
includes taxes & fees
1 Oct - 2 Oct
NEWLY RENOVATED- Long Term Stay.

Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

10.0 out of 10, Exceptional, (4)
"We stayed for over two months in the summer & it was a perfect, cozy apartment. Parking was always available and it’s walking distance from downtown WS and the Historic District. "
The price is NZ$382
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom condo in Downtown Winston-Salem, free parking!

Cute 3 Bedroom Home centrally located in the Triad.

9.8 out of 10, Exceptional, (12)
"Loved the place, was very clean and looked exactly like the photos, beds were super comfortable, was very easy to check in"
Cute 3 Bedroom Home centrally located in the Triad.

Beautiful family home great location in Greensboro

8.6 out of 10, Excellent, (18)
"My family had a great stay during a visit to a university nearby. It was great and we plan to stay again. "
Beautiful family home great location in Greensboro

Spacious 4 bdrm 2.5 ba townhome w/2 car garage in Reedy Fork area of Greensboro

9.2 out of 10, Wonderful, (7)
"Clean and well accommodating "
The price is NZ$670
includes taxes & fees
28 Oct - 29 Oct
Spacious 4 bdrm 2.5 ba townhome w/2 car garage in Reedy Fork area of Greensboro

The Ardmore Executive Suite

3.5 star property
6.0 out of 10, (3)
"Very clean and nice setup "
The price is NZ$419
includes taxes & fees
29 Sept - 30 Sept
The Ardmore Executive Suite

WEST END WHISPER 3 minute walk or drive to Everything. Prime location.

10.0 out of 10, Exceptional, (2)
"Fantastic location, super clean and convenient to all Winston-Salem attractions, walking distance for most, including Reynolda and WFU. Host is available and guests can park in front of the unit. "
WEST END WHISPER 3 minute walk or drive to Everything. Prime location.
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

Find out more about Jamestown

Find out more about Jamestown

Everything you need to know about Jamestown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamestown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jamestown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamestown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamestown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamestown holiday rentals we have selected for you start as low as NZ$219 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jamestown rentals

At Expedia, we put the best Jamestown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamestown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamestown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamestown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Jamestown?

Yes, there are holiday rentals in Jamestown close to High Point City Lake Park, or you can select a more secluded option if you're looking for a relaxing stay. Jamestown is known for its shopping and restaurants.

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

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee: This holiday home rental outside of Jamestown is located near the airport, and has a patio, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals are there in Jamestown?

With 22 Expedia holiday rentals, you're guaranteed 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 Oak Hollow Lake. Other places in town to visit include Castle McCulloch and Mendenhall Homeplace.

What’s a holiday rental in Jamestown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jamestown. Holiday rentals feature extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips or small group gatherings.