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Jamestown Vacation Rentals

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Our top choices for Jamestown vacation rentals

Theater, heated pool/hot tub near HPU/Market

Theater, heated pool/hot tub near HPU/Market
2.0 star property
Jamestown
7.8 out of 10, Good, (6)
"Over all, we had a great stay."
United States
Rebecca H.
$259 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
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, (9)
"Excellent stay for graduation."
United States
Stewart C.
$984 nightly
The price is $1,109
Jan 5 - Jan 6, 2026
Total with taxes and fees
ZenCaza: Perfect Blend of Retreat and Getaway-Prime 5-Bed with Lux King Ensuite

Walden Cabin Experience

Walden Cabin Experience
Stokesdale
10.0 out of 10, Exceptional, (25)
"Wonderful family, memorable visit.Highly recommend "
United States
Vicky Z.
$115 nightly
The price is $127
Jan 5 - Jan 6, 2026
Total with taxes and fees
Walden Cabin Experience

Updated 1BR cottage on private acre+ lot

Updated 1BR cottage on private acre+ lot
Winston-Salem
10.0 out of 10, Exceptional, (18)
"Cutest little place. It was just right for us and the hosts were very responsive."
United States
Wilmarie C.
$115 nightly
The price is $129
Jan 13 - Jan 14, 2026
Total with taxes and fees
Updated 1BR cottage on private acre+ lot

Quaint 2 bed 1 bath cottage style home

Quaint 2 bed 1 bath cottage style home
Kernersville
9.0 out of 10, Wonderful, (41)
"Rough on the outside, clean and well maintained on the inside. Per night cost is low so a very good value."
United States
Arthur F.
$200 nightly
The price is $226
Jan 2 - Jan 3, 2026
Total with taxes and fees
Quaint 2 bed 1 bath cottage style home

Spacious Renovated 3-bedroom with WiFi and AC in tranquil Greensboro

Spacious Renovated 3-bedroom with WiFi and AC in tranquil Greensboro
2.0 star property
Greensboro
10.0 out of 10, Exceptional, (11)
"Great location clean and gorgeous home"
United States
Deondrikk M.
$282 nightly
The price is $318
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious Renovated 3-bedroom with WiFi and AC in tranquil Greensboro

Charming clean 3 bedroom house, big bedrooms with king beds in Greensboro

Charming clean 3 bedroom house, big bedrooms with king beds in Greensboro
Greensboro
10.0 out of 10, Exceptional, (4)
"It was nice and quiet I would totally stay here again."
United States
Manuela G.
$202 nightly
The price is $228
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming clean 3 bedroom house, big bedrooms with king beds in Greensboro

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)
"Wonderful stay! "
United States
Hannah J.
$188 nightly
The price is $212
Jan 2 - Jan 3, 2026
Total with taxes and fees
Log Cabin on Main St. In the ❤️ of Winston Salem. Sleeps 4 comfortably.

Charming 1 bedroom 1926 apt in historic Lindley Park is close to everything.

Charming 1 bedroom 1926 apt in historic Lindley Park is close to everything.
Lindley Park
10.0 out of 10, Exceptional, (13)
"Very nice experience, cool space, very nice host."
United States
Dustin
$165 nightly
The price is $186
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 1 bedroom 1926 apt in historic Lindley Park is close to everything.

Bright & Elegant Home in High Point w/ Deck!

Bright & Elegant Home in High Point w/ Deck!
3.0 star property
High Point
$394 nightly
The price is $422
Jan 4 - Jan 5, 2026
Total with taxes and fees
Bright & Elegant Home in High Point w/ Deck!

Spacious Townhouse In High Point Near HPU & Furniture Market

Spacious Townhouse In High Point Near HPU & Furniture Market
2.0 star property
High Point
9.0 out of 10, Wonderful, (10)
"Close to everything but in a quiet area. Highly recommend"
United States
Frederick W.
$270 nightly
The price is $296
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious Townhouse In High Point Near HPU & Furniture Market

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, (15)
"Very Nice. Overall great experience. "
United States
Lucas H.
$215 nightly
The price is $228
Jan 1 - Jan 2, 2026
Total with taxes and fees
Quietude Place · Stylish 2 Bedroom House with Full Kitchen near HPU

Jude's cozy & convenient downtown studio Apt.

Jude's cozy & convenient downtown studio Apt.
High Point
9.2 out of 10, Wonderful, (11)
"Lovely place, host, and location in town!"
United States
Samir B.
$104 nightly
The price is $117
Jan 6 - Jan 7, 2026
Total with taxes and fees
Jude's cozy & convenient downtown studio Apt.

3 mins from Downtown - PS5, King Bed & EV Charger

3 mins from Downtown - PS5, King Bed & EV Charger
2.0 star property
Winston-Salem
8.8 out of 10, Excellent, (13)
"Super comfortable accommodation! Cute suite close to downtown. Perfect spot. "
United States
Christina H.
$172 nightly
The price is $194
Jan 1 - Jan 2, 2026
Total with taxes and fees
3 mins from Downtown - PS5, King Bed & EV Charger

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, (11)
"Great stay, and just a short walk across the street to The Hillbilly Hideaway for a great breakfast!"
United States
Chris S.
$198 nightly
The price is $211
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 3-bedroom cottage with AC, WiFi in serene Walnut Cove.

The Wooded Grand High Point

The Wooded Grand High Point
High Point
8.0 out of 10, Very Good, (4)
"Clean rooms and house Quiet location Perfect for 2-3 people "
United States
Anne
$270 nightly
The price is $273
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Wooded Grand High Point

Cozy 2bd/1bth +80" TV Movie Room

Cozy 2bd/1bth +80" TV Movie Room
Lindley Park
10.0 out of 10, Exceptional, (2)
"Great setting and close access. Very comfortable rooms and super clean!"
United States
Laura W.
$202 nightly
The price is $228
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy 2bd/1bth +80" TV Movie Room

Little White House Studio w/ Full Kitchen

Little White House Studio w/ Full Kitchen
2.0 star property
Old Irving Park
9.0 out of 10, Wonderful, (17)
"The hosts were responsive and the place was just perfect. It was great fun walking around the neighborhood."
United States
Jennifer C.
$193 nightly
The price is $208
Jan 1 - Jan 2, 2026
Total with taxes and fees
Little White House Studio w/ Full Kitchen

Charming 3-bedroom house in delightful McLeansville with AC, WiFi

Charming 3-bedroom house in delightful McLeansville with AC, WiFi
2.0 star property
McLeansville
10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed our time! Thank you!"
United States
Padonda W.
$307 nightly
The price is $346
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming 3-bedroom house in delightful McLeansville with AC, WiFi

Oasis within a short walk to uptown

Oasis within a short walk to uptown
High Point
10.0 out of 10, Exceptional, (5)
"Great house near HPU. Safe and secure and the fenced in yard was fantastic. "
United States
Jennifer G.
$199 nightly
The price is $211
Jan 4 - Jan 5, 2026
Total with taxes and fees
Oasis within a short walk to uptown
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jamestown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Jamestown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $205 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jamestown rentals

At Expedia, we put the best Jamestown vacation 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 vacation.

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 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.