Jamestown Holiday Rentals

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Our top choices for Jamestown holiday rentals

Theater, heated pool/hot tub near HPU/Market

Theater, heated pool/hot tub near HPU/Market
Jamestown
7.4 out of 10, Good, (8 reviews)
"Owner was easy to communicate with and very responsive. House is older, so if you are expecting top of the line this isn't your place, but if you want a great location, space for a large family with pets, and entertainment this your spot."
United States
MC S.
The price is NZ$605
includes taxes & fees
7 Apr - 8 Apr
Theater, heated pool/hot tub near HPU/Market

ZenCaza: Perfect Blend of Retreat and Getaway-Prime 5-Bed with Lux King Ensuite

ZenCaza: Perfect Blend of Retreat and Getaway-Prime 5-Bed with Lux King Ensuite
Jamestown
10.0 out of 10, Exceptional, (10 reviews)
"Excellent stay for graduation."
United States
Stewart C.
The price is NZ$1,365
includes taxes & fees
31 Mar - 1 Apr
ZenCaza: Perfect Blend of Retreat and Getaway-Prime 5-Bed with Lux King Ensuite

Cazenitah: The Ideal Getaway, Corporate 3BR in Prime Location and Neighborhood

Cazenitah: The Ideal Getaway, Corporate 3BR in Prime Location and Neighborhood
Jamestown
10.0 out of 10, Exceptional, (1 review)
"Betty’s place is very good. At the last minute, I had to find a new location for a birthday dinner To host some family members. The house is much bigger than we thought it would have been. It has all the amenities that you could ask for. Betty was easy to communicate with and her home is extremely clean and comfortable."
United States
Rehshetta W.
The price is NZ$1,216
includes taxes & fees
30 Mar - 31 Mar
Cazenitah: The Ideal Getaway, Corporate 3BR in Prime Location and Neighborhood

Quaint 2 bed 1 bath cottage style home

Quaint 2 bed 1 bath cottage style home
Kernersville
9.0 out of 10, Wonderful, (43 reviews)
"Nice house. Comfortable. Host was easy to talk to. Will stay again if in the area."
United States
Greg C.
The price is NZ$360
includes taxes & fees
29 Mar - 30 Mar
Quaint 2 bed 1 bath cottage style home

Got Cabin Fever? - Grumpy Ol' Goat

Got Cabin Fever? - Grumpy Ol' Goat
Pleasant Garden
8.8 out of 10, Excellent, (16 reviews)
"Charming cabin and the property/grounds overall was fantastic! Teri (host) was very welcoming and gracious. We will stay again, when back in the area to visit!"
United States
Travis T.
The price is NZ$355
includes taxes & fees
28 Mar - 29 Mar
Got Cabin Fever? - Grumpy Ol' Goat

Quiet, newly renovated. Near everything!

Quiet, newly renovated. Near everything!
Winston-Salem
10.0 out of 10, Exceptional, (23 reviews)
"The property was clean, and comfortable in a nice neighborhood close to amenities."
United States
Maria H.
The price is NZ$455
includes taxes & fees
1 Apr - 2 Apr
Quiet, newly renovated. Near everything!

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is NZ$841
includes taxes & fees
7 Apr - 8 Apr
Cozy Cottage: Nature-filled Winston-salem Retreat!

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
Winston-Salem
9.6 out of 10, Exceptional, (8 reviews)
"It was perfect for our needs! Ty so much for a great place to stay!"
United States
Bobby
The price is NZ$448
includes taxes & fees
3 Apr - 4 Apr
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Winston-Salem
10.0 out of 10, Exceptional, (1 review)
The price is NZ$432
includes taxes & fees
29 Mar - 30 Mar
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds

Walden Cabin Experience

Walden Cabin Experience
Stokesdale
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful family, memorable visit.Highly recommend "
United States
Vicky Z.
The price is NZ$237
includes taxes & fees
12 Apr - 13 Apr
Walden Cabin Experience

The Ardmore Executive Suite

The Ardmore Executive Suite
3.5 star property
Winston-Salem
6.0 out of 10, (3 reviews)
"Very clean and nice setup "
United States
Nicholas
The price is NZ$271
includes taxes & fees
8 Apr - 9 Apr
The Ardmore Executive Suite

⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕

⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
Greensboro
9.6 out of 10, Exceptional, (35 reviews)
"Home was very clean with lots of "extras" provided. It was good place for our visit, especially with the fenced yard for our dog. Convenient location for restaurants, groceries, etc."
United States
Jamie K.
The price is NZ$538
includes taxes & fees
4 Apr - 5 Apr
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕

Newly renovated condo near PTI Airport.

Newly renovated condo near PTI Airport.
Greensboro
10.0 out of 10, Exceptional, (8 reviews)
"Place was great. Quiet neighborhood . Would definitely recommend this spot to friends."
United States
kim w.
The price is NZ$470
includes taxes & fees
28 Mar - 29 Mar
Newly renovated condo near PTI Airport.

La Casita .

La Casita .
Winston-Salem
10.0 out of 10, Exceptional, (2 reviews)
"Overall a great place to stay. Super cozy! "
United States
Darren L.
The price is NZ$308
includes taxes & fees
31 Mar - 1 Apr
La Casita .

The Red Door Cabin

The Red Door Cabin
Winston-Salem
10.0 out of 10, Exceptional, (21 reviews)
"Perfect place to stay off the beaten path. Beautiful cabin for a weekend getaway. "
United States
John F.
The price is NZ$461
includes taxes & fees
3 Apr - 4 Apr
The Red Door Cabin

The Hot Tub Hideaway

The Hot Tub Hideaway
Winston-Salem
9.6 out of 10, Exceptional, (31 reviews)
"It was a good stay"
United States
Kim R.
The price is NZ$457
includes taxes & fees
29 Mar - 30 Mar
The Hot Tub Hideaway

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Winston-Salem
9.6 out of 10, Exceptional, (18 reviews)
"Wonderful stay! "
United States
Hannah J.
The price is NZ$412
includes taxes & fees
29 Mar - 30 Mar
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Quietude Place · Stylish 2 Bedroom House with Full Kitchen near HPU

Quietude Place · Stylish 2 Bedroom House with Full Kitchen near HPU
High Point
10.0 out of 10, Exceptional, (17 reviews)
"This was a great stay. The host always provides a nice clean stay, with wonderful amenities. I will definitely stay here again."
United States
Salena L.
The price is NZ$428
includes taxes & fees
29 Mar - 30 Mar
Quietude Place · Stylish 2 Bedroom House with Full Kitchen near HPU

Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.

Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.
Walnut Cove
9.2 out of 10, Wonderful, (13 reviews)
"Such a cute little place that makes you feel like you are home! She has everything here you could have forgotten at home. Peaceful clean and conveniently located close to anything you need"
United States
Candis
The price is NZ$385
includes taxes & fees
29 Mar - 30 Mar
Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.

Close to Downtown-Primary on Main-Fast Internet

Close to Downtown-Primary on Main-Fast Internet
Greensboro
9.4 out of 10, Exceptional, (39 reviews)
"Cute and cozy, great location, host was accessible and made sure we were taken care of, would recommend to anyone wanting a home away from home!"
Canada
Vanina W.
The price is NZ$446
includes taxes & fees
13 Apr - 14 Apr
Close to Downtown-Primary on Main-Fast Internet
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

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$237 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?

Theater, heated pool/hot tub near HPU/Market: This highly rated holiday home rental in Jamestown offers a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals are there in Jamestown?

With 25 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.