Holiday Rentals in Greenwood

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Our top choices for Greenwood holiday rentals

9.8 out of 10, Exceptional, (12)
"Clean and comfortable. Great place to stay while we visited our son and enjoyed some home cooking. "
United States
Todd
The price is €281
includes taxes & fees
29 Dec - 30 Dec
Charming 3 Bedroom House away from it all but Close to everything
9.4 out of 10, Exceptional, (3)
"Had a great stay, love the outdoor porch and lighting!"
United States
Heather W.
The price is €206
includes taxes & fees
26 Dec - 27 Dec
Unplug and unwind in this charming loft cabin nestled on the water’s edge.
10.0 out of 10, Exceptional, (3)
"Great space! Lance was always communicating with me. Property was clean and had everything we needed. "
United States
Wendy
Bright & Roomy 2BR | 1st Floor Retreat | #65
9.4 out of 10, Exceptional, (8)
"We really enjoyed our stay, the people could not have been nicer and were very responsive. Highly recommended. Thanks!"
United States
Chad S.
The Pilot’s Pad - Private Studio Apartment on 75 acres + airway strip + fishing pond
9.4 out of 10, Exceptional, (22)
"Nice place good location "
United States
Clarissa G.
The price is €314
includes taxes & fees
24 Jan - 25 Jan 2026
Blue House - Cozy 3 Bedroom, King Bed, Rotary Park
3.5 star property
9.2 out of 10, Wonderful, (1084)
"Loved the suite room "
United States
Louis
The price is €93
includes taxes & fees
7 Jan - 8 Jan 2026
WaterWalk Extended Stay by Wyndham Kansas City - Overland Pk

Apartment in Midtown - Westport

Spacious Plaza Stay: 1bd/1ba
8.8 out of 10, Excellent, (16)
"We stayed for a quick visit to KC. Location was great and the check-in process was easy and fast. Host provided instructions promptly and it was easy to follow. The apartment was clean and spacious. "
United States
Jesus L.
The price is €127
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious Plaza Stay: 1bd/1ba
9.6 out of 10, Exceptional, (9)
"We really enjoyed our stay here. It's a very comfortable second floor unit with two beds (one in its own bedroom), full bathroom, laundry, and full kitchen. It had everything we needed when traveling with an infant. The location was also good - easy to get around to all the main attractions in the Kansas City area. I'd recommend it as a great place to stay!"
United States
Jon K.
The price is €151
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy 2nd Floor unit Near Plaza and Westport | 08

Apartment in South Kansas City

10 minutes to the Stadiums
2.0 star property
9.8 out of 10, Exceptional, (6)
The price is €86
includes taxes & fees
5 Jan - 6 Jan 2026
10 minutes to the Stadiums

Condo in Park Central-Research Park

The View - 1 Bed Plaza Condo + Amazing View
9.4 out of 10, Exceptional, (18)
"The place was very clean and extremely comfortable with great amenities! The location was also excellent with a large park across the street and the nelson art museum very nearby. We would definitely stay again."
United States
Robert B.
The price is €229
includes taxes & fees
11 Jan - 12 Jan 2026
The View - 1 Bed Plaza Condo + Amazing View

Apartment in Midtown - Westport

Simple PLAZA Comfort!
8.0 out of 10, Very good, (13)
"Our unit was nice! Only frustrating thing is that you don’t get access to the buildings parking lot. Building also has a different name than what is listed. "
United States
Romina
The price is €118
includes taxes & fees
7 Jan - 8 Jan 2026
Simple PLAZA Comfort!

Holiday Home in West Plaza

Charming Hideaway in Westport 15
9.2 out of 10, Wonderful, (42)
"We had a very good stay"
United States
Lakeisha R.
The price is €173
includes taxes & fees
19 Jan - 20 Jan 2026
Charming Hideaway in Westport 15
9.6 out of 10, Exceptional, (12)
"This place was very neat - a retro, comfortable spot that makes a great home-base for any trip to KC without the hassle of the city. It was clean and cozy, with a great shower!"
United States
Robbie M.
The price is €224
includes taxes & fees
27 Dec - 28 Dec
Retro Funky Stay less than 10 minutes from Arrowhead!

Holiday Home in Midtown - Westport

1-Bedroom Near the Plaza & Scenic Park I 13
9.2 out of 10, Wonderful, (24)
"We couldn’t have asked for a better home base to explore Kansas City. We loved the tree-lined neighborhood and huge green space/park for morning walks. We were minutes away from great food and great art and awesome vintage stores (and any other kind of shopping you’d want to do.) The updated first floor unit was clean and comfy and equipped with plenty of towels, kitchenware and bedding. Loved it."
United States
Cindy L.
The price is €146
includes taxes & fees
5 Jan - 6 Jan 2026
1-Bedroom Near the Plaza & Scenic Park I 13

Chalet in Raytown

Cottage KC
8.0 out of 10, Very good, (3)
"We stayed here for the night while attending an event at Kauffman Stadium. The hosts were nice and very responsive. We had a payment issue before our stay and they worked with me to get it taken care of. The cottage was clean, the bed was comfortable. It was just a few minutes from the stadium as well. I would stay here again. "
United Kingdom
Becky F.
The price is €130
includes taxes & fees
4 Jan - 5 Jan 2026
Cottage KC
9.2 out of 10, Wonderful, (33)
"Great location and great communication with owners "
United States
Jeremy B.
The price is €231
includes taxes & fees
19 Jan - 20 Jan 2026
The Nelson - Gorgeous Condo Walkable to the Plaza + Streetcar!
9.8 out of 10, Exceptional, (55)
"Clean place. Will stay again."
United States
Keith D.
The price is €164
includes taxes & fees
22 Jan - 23 Jan 2026
Newly Renovated Stylish 3rd Floor Apartment 5 mins from Country Club Plaza
9.8 out of 10, Exceptional, (119)
"Great place in a great location."
United States
Reece
The price is €258
includes taxes & fees
5 Jan - 6 Jan 2026
Completely restored 1885 Queen Ann style home located next to the temple lot.

Condo in Midtown - Westport

Cute Midtown 1 Bedroom
9.0 out of 10, Wonderful, (4)
"We spent 2 nights to catch a Chiefs game and enjoy a night in KC.The space is the perfect size and perfectly priced.We were able to schedule a late checkout which was much needed!We’ll definitely be back for another weekend away!"
United States
Justine H.
The price is €158
includes taxes & fees
4 Jan - 5 Jan 2026
Cute Midtown 1 Bedroom

Apartment in Midtown - Westport

★ King Bed ★ Uptown Theater★
9.4 out of 10, Exceptional, (14)
"Really clean and had everything I needed, great stay!"
United States
William B.
The price is €176
includes taxes & fees
28 Dec - 29 Dec
★ King Bed ★ Uptown Theater★
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

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, apart-hotels, 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 €93 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. 

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its restaurants and shopping.

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

CASA AZUL DE VIDA. 1 min next to the Street Car.: This holiday home rental outside of Greenwood is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

What can I see and do in Greenwood?

Explore the area and family-friendly sights such as Blue Spring, or get out into nature at a spot like Cave Spring Interpretive Center. GEHA Field at Arrowhead Stadium and Missouri Town 1855 are a couple of places you'll find in the wider area.

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 kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you to 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 popular choice for small groups.