Photo by Roger Younce

Jamestown Holiday Rentals

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Holiday Rentals in Jamestown

High ceiling house close to downtown
4.0 out of 10, (1)
"The house was not in a good neighborhood. Major issues: Chained dog barked all night, the washing machine didn’t work, had to call to find the linens which were stored in a file cabinet in a bedroom, showed up during check in time and cleaning staff was still there, hardly any dishes on site so forget about cooking a meal there. Place was a disappointment at best, especially for the overall cost."
The price is NZ$441
per night
5 Jun - 6 Jun
High ceiling house close to downtown
Bright Greensboro Escape ~ 1 Mi to Downtown
9.6 out of 10, Exceptional, (22)
"I stayed with my son at this property for a week while he swam at the Nationals Swim Meet at the Greensboro swim coliseum. The property was perfect for us--a 10 minute drive from the venue, but in an established, safe neighborhood surrounded by beautiful trees and plentiful walking paths. It is walkable to great local restaurants and coffee shops, and a short drive to great shopping, dining, grocery stores (Trader Joe's, Whole Foods, etc.). Highly recommend. We'll definitely be back!!"
Bright Greensboro Escape ~ 1 Mi to Downtown
Newly renovated home away from home!!!
10.0 out of 10, Exceptional, (41)
"Several friends were in town visiting for an event in Winston-Salem. The house was extremely clean and comfortable. We were able to enjoy the event and relax after in a great space."
The price is NZ$371
per night
4 Jun - 5 Jun
Newly renovated home away from home!!!
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Modern Bungalow | Game Room | Fire Pit | Grill
9.8 out of 10, Exceptional, (11)
"House was great for our family with 2 high schoolers. Very clean and sufficiently stocked. Comfortable beds, comfy couch, lots of counter space in kitchen. Having the outdoor patio space was terrific for enjoying the warm weather while grilling out! We had a great stay!"
The price is NZ$479
per night
4 Jun - 5 Jun
Modern Bungalow | Game Room | Fire Pit | Grill
Updated High Point Retreat w/ Pool & Backyard
10.0 out of 10, Exceptional, (8)
"Check in was easy and our contact person, Beth, was friendly and accommodating. The house was very clean, the kitchen well stocked, and the rooms were well furnished. The location of the house to the university and restaurants was perfect. Thank you to Beth, the cleaners, and the homeowners for a wonderful stay and for allowing us to have our other family member, our dog, with us. You can tell they put a lot of thought into making your visit comfortable. In choosing this home, be mindful of...
Updated High Point Retreat w/ Pool & Backyard
Royal 3 Bedroom House w/ Pool
10.0 out of 10, Exceptional, (2)
"Very nice home and lovely decorations. The beds were comfy, neighborhood is nice, and we were very appreciative that they could accommodate us on short notice."
The price is NZ$710
per night
4 Jun - 5 Jun
Royal 3 Bedroom House w/ Pool
North Carolina Retreat - Deck, Grills & Lake Views
9.8 out of 10, Exceptional, (16)
"Good place to gather as a family"
North Carolina Retreat - Deck, Grills & Lake Views
Cozy Townhome in a Great Location
9.8 out of 10, Exceptional, (9)
"Great place for our Mother’s Day weekend"
Cozy Townhome in a Great Location
The Red Door Cabin
10.0 out of 10, Exceptional, (5)
"Serenity without isolation"
The Red Door Cabin
Cozy Home in Central Location, Gboro & High Point!
10.0 out of 10, Exceptional, (28)
"This is such a cute house that is so conveniently located to downtown Greensboro. The house was very clean and had everything you could need to have a fabulous, fun weekend with friends!"
The price is NZ$439
per night
16 Jun - 17 Jun
Cozy Home in Central Location, Gboro & High Point!
Quaint 2 bed 1 bath cottage style home
9.4 out of 10, Exceptional, (18)
"Property owner had excellent communication right up to the time we walked in the door. The property was perfect. Clean, well stocked. Very quiet area. HIGHLY recommended."
The price is NZ$394
per night
16 Jun - 17 Jun
Quaint 2 bed 1 bath cottage style home
Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt
9.8 out of 10, Exceptional, (14)
"Nice, quiet neighborhood. Host was excellent communicator"
Hot Tub Heated NOW Salt Pool Private Resort Stay Mins to HPU & DT Furniture Mkt
Unique, All-Encompassing Family Farmstead!
10.0 out of 10, Exceptional, (13)
"Excellent property very quiet and peaceful...perfect!"
Unique, All-Encompassing Family Farmstead!
The Farmhouse Retreat near Furniture Mkt and HPU
9.8 out of 10, Exceptional, (29)
"Great location to HPU. Recommend for any family coming to see the school or students."
The price is NZ$532
per night
17 Jun - 18 Jun
The Farmhouse Retreat near Furniture Mkt and HPU
Charming Remodeled 4 Bedroom Home in Downtown High Point
10.0 out of 10, Exceptional, (44)
"The house was beautiful and had so many provisions not listed, right down to shampoo that we had forgotten. The host.was very accommodating and let us check in early on Friday. We come here every year. We will definitely be back to this house next year and we're actually thinking about returning this summer trying to find some open dates that she has. Thank you, we had a wonderful time!"
Charming Remodeled 4 Bedroom Home in Downtown High Point
Great High Point Location adj to JH Adams Inn- Newly Renovated
10.0 out of 10, Exceptional, (47)
"Great area great place "
Great High Point Location adj to JH Adams Inn- Newly Renovated
Shalimar Estates @ Emerywood and Downtown/HPU
The price is NZ$1,870
per night
4 Jun - 5 Jun
Shalimar Estates @ Emerywood and Downtown/HPU
Chic & Cozy Greensboro Home, 2 Mi to Dtwn!
9.6 out of 10, Exceptional, (29)
"Wonderful experience and Beth is the best host! Very attentive. Thank you!"
Chic & Cozy Greensboro Home, 2 Mi to Dtwn!
Walden Cabin Experience
10.0 out of 10, Exceptional, (15)
"It was.. AWESOME! It was so cool! John and his wife were amazing, went thru everything with me. Just an incredibly cool experience. Ill be going back!!! Thanks, Dirk R."
The price is NZ$224
per night
4 Jun - 5 Jun
Walden Cabin Experience
Lovely 3 Bedroom Home Near Downtown Greensboro
10.0 out of 10, Exceptional, (2)
"I would Highly Recommend staying here! Very convenient to High Point Market, quiet neighborhood, and close to a ton of great local restaurants! Very clean and had everything that you’d need for a great evening after a long day at Market."
Lovely 3 Bedroom Home Near Downtown Greensboro
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See all available properties in Jamestown
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.

Other types of properties in Jamestown you may be interested in

Marriott Greensboro Downtown
4.0 star property
8.4 out of 10, Very good, (957)
"Good location to walk downtown and the Grasshopper baseball stadium."
The price is NZ$310
per night
4 Jul - 5 Jul
Marriott Greensboro Downtown
Holiday Inn Greensboro Coliseum, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Rooms"
The price is NZ$209
per night
9 Jun - 10 Jun
Holiday Inn Greensboro Coliseum, an IHG Hotel
Sheraton Greensboro at Four Seasons
3.5 star property
8.6 out of 10, Excellent, (1013)
"The propery is nice, quiet,clean, shoping center ,convention center on the side is really nice"
The price is NZ$248
per night
16 Jun - 17 Jun
Sheraton Greensboro at Four Seasons
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jamestown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jamestown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Jamestown. Seeing all the best attractions is bound to make you fall in love with Jamestown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Jamestown short-term rentals, that won’t be hard to do.

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?

Midcentury Poolside Retreat Near Greensboro/High Point: This highly rated holiday home rental in Jamestown is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Jamestown?

With 17 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.

Recent reviews of Jamestown properties
Expedia verified reviews