Wilmington Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Wilmington holiday rentals

A two-story house with a front porch, a central entrance, and a symmetrical window arrangement.

1. Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville
Palmyra
10.0 out of 10, Exceptional, (56 reviews)
"Excellent experience. Very affordable with the highest standards. Many extras included and everything necessary was included to the highest standards. Great place to bring Fido too. Overall an outstanding place to stay!"
United States
David M.
The price is AU$337
includes taxes & fees
12 Nov - 13 Nov
Private Guest Suite by Wineries/Orchards/Cville
A modern kitchen with stainless steel appliances, a dining table with chairs, and a window with blinds.

2. Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
9.2 out of 10, Wonderful, (154 reviews)
"Had a great stay! Everything was as expected and the property was nice."
United States
Jules R.
The price is AU$270
includes taxes & fees
17 Nov - 18 Nov
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Room

3. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Excellent For Couples Getaways!!!"
United States
Jonathan
The price is AU$181
includes taxes & fees
12 Nov - 13 Nov
SONSAK - MONTICELLO
A modern kitchen with a large island, a built-in oven, and a window with curtains.

4. Bluebird Cottage B: Quiet, Firepit, Patio, Games

Bluebird Cottage B: Quiet, Firepit, Patio, Games
Palmyra
10.0 out of 10, Exceptional, (63 reviews)
"A wonderful cottage that meets all of your needs! Clean, quiet and cozy! Highly recommend!"
United States
Jane C.
The price is AU$367
includes taxes & fees
30 Nov - 1 Dec
Bluebird Cottage B: Quiet, Firepit, Patio, Games
A compact kitchen with a stove, oven, coffee maker, and a refrigerator.

5. Pine Grove Apartment: Visit Monticello, wineries, UVA

Pine Grove Apartment: Visit Monticello, wineries, UVA
Troy
9.6 out of 10, Exceptional, (7 reviews)
"Was a great place to lay our heads for the night while we were in town for a wedding very cozy and had everything you could need would highly recommend!"
United States
Jordan
The price is AU$308
includes taxes & fees
16 Nov - 17 Nov
Pine Grove Apartment: Visit Monticello, wineries, UVA
A wooden deck with wicker chairs and a table, surrounded by a wooden railing and greenery.

6. Visit Monticello, Wineries, UVA & More

Visit Monticello, Wineries, UVA & More
Troy
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay! Only a 25 min ride from Charlottesville!"
United States
Camryn S.
The price is AU$689
includes taxes & fees
16 Nov - 17 Nov
Visit Monticello, Wineries, UVA & More
A compact kitchen with a microwave, toaster, and sink. There is a dining area with a table and chairs in the background.

7. The Country Retreat – Cozy Comfort Meets Peaceful Countryside

The Country Retreat – Cozy Comfort Meets Peaceful Countryside
Scottsville
9.4 out of 10, Exceptional, (6 reviews)
"Nice clean place out in the country. We were there for Memorial Day weekend and had a nice relaxing time."
United States
Michael L.
The price is AU$585
includes taxes & fees
16 Nov - 17 Nov
The Country Retreat – Cozy Comfort Meets Peaceful Countryside
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

8. Spacious 4-bedroom building in wonderful Louisa with AC

Spacious 4-bedroom building in wonderful Louisa with AC
Louisa
The price is AU$889
includes taxes & fees
2 Dec - 3 Dec
Spacious 4-bedroom building in wonderful Louisa with AC
Directly Across Historic Michie Tavern

9. Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (36 reviews)
"Perfect for a short stay."
United States
Gaye W.
The price is AU$221
includes taxes & fees
12 Nov - 13 Nov
Unit 5 - Cozy Lower Level Studio Suite
Directly Across Historic Michie Tavern

10. Unit 4 - Luxury King Suite with Private Balcony

Unit 4 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (16 reviews)
"Great location, clean and organized and comfortable. Hope to stay here again. "
United States
Ellie T.
The price is AU$328
includes taxes & fees
1 Dec - 2 Dec
Unit 4 - Luxury King Suite with Private Balcony
Directly Across Historic Michie Tavern

11. Unit 3 - Luxury King Suite with Private Balcony

Unit 3 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (37 reviews)
"These units were very well thought out and comfortable. Bed was great, kitchen stocked with useful tools and basics that were so nice to have at our disposal. It’s clean, modern and our stay was very restful. Checking in and out is a breeze - door code sent to you 15 minutes before check-in. Would definitely go back if we’re ever in the area again."
United States
Linda
The price is AU$328
includes taxes & fees
7 Dec - 8 Dec
Unit 3 - Luxury King Suite with Private Balcony
Directly Across Historic Michie Tavern

12. Unit 1_Expansive Luxury Suite for up to 4 Persons

Unit 1_Expansive Luxury Suite for up to 4 Persons
Charlottesville
10.0 out of 10, Exceptional, (23 reviews)
"Great hosts and beautiful location!"
United States
Mallory B.
The price is AU$538
includes taxes & fees
29 Nov - 30 Nov
Unit 1_Expansive Luxury Suite for up to 4 Persons
A covered patio with two sofas, a table with food and drinks, and a view of a vineyard.

13. Fern Cottage Summary:

Fern Cottage Summary:
Gordonsville
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The house was clean and well furnished. Recommend for anyone staying in the area."
United States
Gary W.
The price is AU$974
includes taxes & fees
2 Dec - 3 Dec
Fern Cottage Summary:
Directly Across Historic Michie Tavern

14. Unit 2_Expansive Luxury Suite for up to 4 Persons

Unit 2_Expansive Luxury Suite for up to 4 Persons
Charlottesville
10.0 out of 10, Exceptional, (15 reviews)
"We enjoy everything about the place. Clean, easy access, outdoor spaces, and new cool design "
United States
Susan
The price is AU$657
includes taxes & fees
25 Nov - 26 Nov
Unit 2_Expansive Luxury Suite for up to 4 Persons
A two-story house with a porch and a garage, surrounded by a well-maintained lawn and trees.

15. Ranchito

Ranchito
2.0 star property
Troy
The price is AU$1,493
includes taxes & fees
25 Nov - 26 Nov
Ranchito
A spacious living room with a high ceiling, a staircase, and a television mounted on the wall.

16. Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!

Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
Keswick
9.8 out of 10, Exceptional, (54 reviews)
"Nice cabin in a beautiful spot, location is great -- easy access to VA wine country!"
United States
Ethan W.
The price is AU$852
includes taxes & fees
20 Nov - 21 Nov
Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
A compact bedroom with a single bed, a wooden nightstand, a small table with a vase, and a chair. A bathroom is visible through an open door.

17. Charming Historic Carriage House Studio Apartment

Charming Historic Carriage House Studio Apartment
Charlottesville
10.0 out of 10, Exceptional, (24 reviews)
"Cozy and charmy. Enjoyed the stay and would do again."
United States
Michael I.
The price is AU$416
includes taxes & fees
24 Nov - 25 Nov
Charming Historic Carriage House Studio Apartment
A wooden deck with wicker chairs and a table, surrounded by a wooden railing and greenery.

18. Visit Monticello, Wineries, UVA: Room for a Crowd

Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
9.2 out of 10, Wonderful, (26 reviews)
"Great place for us, comfortable and well-equipped."
United States
Lynn F.
The price is AU$923
includes taxes & fees
16 Nov - 17 Nov
Visit Monticello, Wineries, UVA: Room for a Crowd
A fire pit surrounded by black Adirondack chairs in a forested outdoor area.

19. Pine and Vine: 8 Acres + Winery & Family Retreat

Pine and Vine: 8 Acres + Winery & Family Retreat
Gordonsville
10.0 out of 10, Exceptional, (3 reviews)
"This house is fantastic and meant for small groups. The floor plan is open and the rooms are simply perfect."
United States
Lisa
The price is AU$1,310
includes taxes & fees
8 Dec - 9 Dec
Pine and Vine: 8 Acres + Winery & Family Retreat
A two-story house with a porch and a garage, surrounded by a well-maintained lawn and trees.

20. Ranchito: Near Keswick Hall & Local Vineyards

Ranchito: Near Keswick Hall & Local Vineyards
Troy
The price is AU$1,533
includes taxes & fees
25 Nov - 26 Nov
Ranchito: Near Keswick Hall & Local Vineyards
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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Find holiday rentals that suit your style

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Top Wilmington Hotel Reviews

A reception area with a counter, seating, and artwork on the walls.
Best Western Plus Crossroads Inn & Suites

Best Western Plus Crossroads Inn & Suites

Best Western Plus Crossroads Inn & Suites
Gordonsville

10/10 Excellent

hotel was very affordable option outside of town - short drive to Monticello. Breakfast was awesome!!
Australia
sue
Reviewed September 27, 2017
Best Western Plus Crossroads Inn & Suites

Find out more about Wilmington

Everything you need to know about Wilmington 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 Wilmington 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 Wilmington holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Wilmington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wilmington. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wilmington 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 Wilmington holiday rentals we have selected for you start as low as AU$181 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wilmington rentals

At Expedia, we put the best Wilmington 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 Wilmington 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 Wilmington 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 Wilmington. 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 a holiday rental in Wilmington?

Yes, there are holiday rentals close to the most popular sights in Wilmington, or you can select a more secluded option if you're looking for a relaxing stay.

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

Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland: This holiday home rental outside of Wilmington offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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 a selection of games.

What’s there to see and do in Wilmington?

While exploring the area, visit family-friendly sights like Louisa Town Park, or get outside and enjoy nature at Fluvanna Heritage Trail. In the wider area, you’ll find Layz S Ranch and Tasting Room & Taphouse at Mount Ida Reserve.

What’s a holiday rental in Wilmington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wilmington. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.