Jamestown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Jamestown holiday rentals

Pool

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 HK$1,559
HK$2,689 total
includes taxes & fees
13 Apr - 14 Apr
Theater, heated pool/hot tub near HPU/Market
Interior

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 HK$3,454
HK$6,455 total
includes taxes & fees
31 Mar - 1 Apr
ZenCaza: Perfect Blend of Retreat and Getaway-Prime 5-Bed with Lux King Ensuite
Interior

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

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 HK$893
HK$1,850 total
includes taxes & fees
13 Apr - 14 Apr
Quaint 2 bed 1 bath cottage style home
Exterior

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 HK$1,022
HK$1,595 total
includes taxes & fees
30 Mar - 31 Mar
Got Cabin Fever? - Grumpy Ol' Goat
Fridge, microwave, oven, stovetop

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 HK$909
HK$2,053 total
includes taxes & fees
1 Apr - 2 Apr
Quiet, newly renovated. Near everything!
Interior

Cozy Cottage: Nature-filled Winston-salem Retreat!

Cozy Cottage: Nature-filled Winston-salem Retreat!
3.0 star property
Winston-Salem
The price is HK$1,488
HK$3,822 total
includes taxes & fees
30 Mar - 31 Mar
Cozy Cottage: Nature-filled Winston-salem Retreat!
Smart TV, fireplace

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 HK$1,121
HK$2,010 total
includes taxes & fees
3 Apr - 4 Apr
Charming 2-bedroom cabin with WiFi in brilliant Winston-Salem
2 bedrooms, iron/ironing board, WiFi, bed sheets

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 HK$744
HK$1,907 total
includes taxes & fees
12 Apr - 13 Apr
Modern 2BR Retreat | 85” TV Ultra-Comfy king Beds
Property grounds

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 HK$783
HK$1,077 total
includes taxes & fees
17 Apr - 18 Apr
Walden Cabin Experience
Private kitchen

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 Ardmore Executive Suite
Exterior

⭐️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 HK$1,324
HK$2,446 total
includes taxes & fees
4 Apr - 5 Apr
⭐️CASA MARIA⭐️⛳️📚🏥🏟🌮🐕
Interior

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 HK$1,057
HK$2,155 total
includes taxes & fees
30 Mar - 31 Mar
Newly renovated condo near PTI Airport.
Outdoor dining

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 HK$533
HK$1,398 total
includes taxes & fees
30 Mar - 31 Mar
La Casita .
Exterior

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 HK$1,245
HK$2,062 total
includes taxes & fees
3 Apr - 4 Apr
The Red Door Cabin
1 bedroom

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 HK$1,245
HK$2,080 total
includes taxes & fees
5 Apr - 6 Apr
The Hot Tub Hideaway
Exterior

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 HK$881
HK$1,854 total
includes taxes & fees
30 Mar - 31 Mar
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.
Fridge, microwave, oven, stovetop

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 HK$822
HK$1,948 total
includes taxes & fees
1 Apr - 2 Apr
Quietude Place · Stylish 2 Bedroom House with Full Kitchen near HPU
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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 HK$1,097
HK$1,855 total
includes taxes & fees
5 Apr - 6 Apr
Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.
Interior

Close to Downtown-Primary on Main-Fast Internet

Close to Downtown-Primary on Main-Fast Internet
Greensboro
9.4 out of 10, Exceptional, (40 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 HK$790
HK$1,967 total
includes taxes & fees
6 Apr - 7 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamestown Hotel Reviews

Proximity Hotel

Proximity Hotel

10/10 Excellent
"Staff were professional and very helpful "
Emmanuel 1-night trip
Posted 1 hour 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
  • Use the map to find apartments and other holiday homes in the Jamestown neighbourhood you prefer
  • 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 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.