Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Greenwood holiday rentals

Outdoor dining
Charming family retreat

Charming family retreat

Charming family retreat
Greenwood
10.0 out of 10, Exceptional, (1)
"If u really wanted stay in the heart of greenwood it’s the perfect place to stay every thing about this house is perfect "
United States
Jamaal C.
Charming family retreat
Property grounds
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Winona
10.0 out of 10, Exceptional, (1)
"This is a cute little rustic cabin. Chad was very friendly and open to suggestions due to being a first time host. "
United States
Trey H.
The price is NZ$319
includes taxes & fees
11 Jan - 12 Jan 2026
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.
Dining
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Grenada
10.0 out of 10, Exceptional, (11)
"Nice quiet and clean location to share with family and friends"
United States
Janet T.
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Fridge, microwave, oven, stovetop
The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake

The Get-A-Way at Grenada lake
Grenada
9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay at. The getaway Place was fully stocked and exceptionally clean, we expect to visit again in the fall and will definitely book this place again. ! Host is great, responded to questions almost immediately."
United States
David S.
The price is NZ$628
includes taxes & fees
28 Dec - 29 Dec
The Get-A-Way at Grenada lake
Fridge, microwave, oven, stovetop
Charming condo 3-bedroom 2 bath, 2 living rooms! Stocked kitchen, laundry room

Charming condo 3-bedroom 2 bath, 2 living rooms! Stocked kitchen, laundry room

Charming condo 3-bedroom 2 bath, 2 living rooms! Stocked kitchen, laundry room
2.0 star property
Grenada
The price is NZ$530
includes taxes & fees
26 Dec - 27 Dec
Charming condo 3-bedroom 2 bath, 2 living rooms! Stocked kitchen, laundry room
Smart TV
The Bleu..

The Bleu..

The Bleu..
Itta Bena
10.0 out of 10, Exceptional, (1)
"Very clean in a nice place to stay not that far from greenwood easy to get to"
United States
Jamaal C.
The price is NZ$658
includes taxes & fees
26 Dec - 27 Dec
The Bleu..
Private kitchen
Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona
Winona
10.0 out of 10, Exceptional, (1)
"First time staying in a cabin and was absolutely impressed! It was such a peaceful stay especially coming from being in the daily city life! David was awesome at communicating. Will be reserving again for sure!"
United States
Cierra O.
The price is NZ$528
includes taxes & fees
26 Dec - 27 Dec
Charming ranch style log cabin with AC in scenic Winona
Interior
Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC
Winona
6.0 out of 10, (1)
"I had a hard time find this place, there need to be sign on old mountain road tell u how to get there. I had to clean one of the bathroom the shower was not clean. There are French door when u enter this place. There need to be some blind to the door."
United States
sherrida r.
The price is NZ$746
includes taxes & fees
28 Dec - 29 Dec
Charming 3-bedroom barn in quaint Winona with AC
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 Greenwood Hotel Reviews

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

10/10 Excellent
"Very attentive staff. Good breakfast, freshness and variety. "
Anita 1-night trip
Posted 5 days ago
Holiday Inn Express and Suites Winona North by IHG

Find out more about Greenwood

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

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. 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 Greenwood 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 Greenwood holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood 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 Greenwood 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 Greenwood 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 Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals in Greenwood close to The Mississippi Gift Company, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Greenwood has a good selection of restaurants. Make sure you have time to check out the cafés and shopping during your trip.

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

Charming family retreat : This highly rated holiday home rental in Greenwood offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Greenwood?

Choose from 3 Expedia holiday rentals in Greenwood for a memorable holiday.

What can I see and do in Greenwood?

Veterans Memorial Park and Broad Street Park are a couple of scenic spots to enjoy the outdoors, whereas Museum of the Mississippi Delta is one of the cultural attractions. The Mississippi Gift Company and Greenwood Mall are other places to visit while you're in town.

What are holiday rentals like in Greenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenwood. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.