Greenwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Greenwood vacation rentals

A cozy cabin-style room with a wooden interior, a bed with a blue quilt, a dresser, a refrigerator, a desk with a chair, and a mounted TV.

1. Horseshoe Lodges Cabins & RV Park

Horseshoe Lodges Cabins & RV Park
3.0 star property
Midland
7.8 out of 10, Good, (177 reviews)
"Cozy little cabins to stay in they were great"
United States
Justn
The price is CA $88
CA $94 total
includes taxes & fees
Nov 9 - Nov 10
Horseshoe Lodges Cabins & RV Park
A kitchen with wooden cabinets, a countertop, and a built-in oven.

2. 1 Bed, 1 Bath High End RV, Fully Furnished, Pet Friendly

1 Bed, 1 Bath High End RV, Fully Furnished, Pet Friendly
Midland
8.0 out of 10, Very good, (1 review)
"It was like going camping. "
United States
Blake B.
The price is CA $95
CA $215 total
includes taxes & fees
Nov 9 - Nov 10
1 Bed, 1 Bath High End RV, Fully Furnished, Pet Friendly
A hot tub area with a view of a landscape through a window, surrounded by dark wooden walls and a ceiling with exposed beams and string lights.

3. Midland's Most Private Tiny Cottage

Midland's Most Private Tiny Cottage
Midland
10.0 out of 10, Exceptional, (20 reviews)
"Such a cute cottage and absolutely loved it! The hot tub is a plus! Would definitely book again! "
United States
Amanda C.
The price is CA $138
CA $238 total
includes taxes & fees
Nov 16 - Nov 17
Midland's Most Private Tiny Cottage
A swimming pool with a water feature, lounge chairs, and a building with multiple windows.

4. 1 King Bed | Non-Smoking, Shower

1 King Bed | Non-Smoking, Shower
Midland
10.0 out of 10, Exceptional, (90 reviews)
"We appreciated how friendly the staff was and loved the spacious room for two."
United States
Anonymous traveller
The price is CA $100
CA $114 total
includes taxes & fees
Nov 13 - Nov 14
1 King Bed | Non-Smoking, Shower
A compact kitchen with a central island, a refrigerator, and a microwave.

5. Los pinitos Charming 1-bedroom cottage

Los pinitos Charming 1-bedroom cottage
midland
10.0 out of 10, Exceptional, (2 reviews)
"Extremely nice place to stay. Everything was super easy and straightforward to make the reservation and during my stay. Great communication. Very convenient to downtown. Would definitely stay again when in Midland!"
United States
Kimberly '.
The price is CA $127
CA $226 total
includes taxes & fees
Nov 15 - Nov 16
Los pinitos Charming 1-bedroom cottage
A compact kitchen with wooden cabinets, a countertop, a coffee maker, and a trash can.

6. Cozy 1-bedroom 5th wheel perfect for a couple or solo traveler

Cozy 1-bedroom 5th wheel perfect for a couple or solo traveler
Midland
The price is CA $127
CA $234 total
includes taxes & fees
Dec 9 - Dec 10
Cozy 1-bedroom 5th wheel perfect for a couple or solo traveler
A compact kitchen with wooden cabinets, a sink, a stove, and a microwave.

7. Modern 1BR RV Retreat

Modern 1BR RV Retreat
Midland
The price is CA $127
CA $227 total
includes taxes & fees
Nov 13 - Nov 14
Modern 1BR RV Retreat
A modern living room with a sofa, coffee table, and a dining area with a white table and placemats.

8. Spacious Modern Apartment, Queen Bed • Twin Beds • Sofa Bed

Spacious Modern Apartment, Queen Bed • Twin Beds • Sofa Bed
Midland
10.0 out of 10, Exceptional, (1 review)
"Great location. Quiet and comfortable. Enjoyed treats left for us. Also bath products were nice."
United States
Mary E.
The price is CA $177
CA $295 total
includes taxes & fees
Nov 17 - Nov 18
Spacious Modern Apartment, Queen Bed • Twin Beds • Sofa Bed
A kitchen with dark wood flooring, a refrigerator, a sink, and a countertop.

9. 🏡 2 bedrooms, 1 bathroom 🛁 cozy, modern apartment. With sofa bed 🛋️

🏡 2 bedrooms, 1 bathroom 🛁 cozy, modern apartment. With sofa bed 🛋️
Midland
8.0 out of 10, Very good, (11 reviews)
"Great location, place was clean and comfortable. "
United States
Dave S.
The price is CA $182
CA $321 total
includes taxes & fees
Nov 13 - Nov 14
🏡 2 bedrooms, 1 bathroom 🛁 cozy, modern apartment. With sofa bed 🛋️
A dining area with a dark wooden table surrounded by wicker chairs and leather ottomans.

10. Executive 3 bedroom townhouse. Close to sports complex/Chevron/OXY/EOG

Executive 3 bedroom townhouse. Close to sports complex/Chevron/OXY/EOG
Midland
9.8 out of 10, Exceptional, (57 reviews)
"Everything was perfect. The house was clean and fully stocked with everything you needed. The communication was quick and check in was very easy. Will definitely book again if available."
United States
James
Executive 3 bedroom townhouse. Close to sports complex/Chevron/OXY/EOG
A swimming pool with a water feature, lounge chairs, and a building with multiple windows.

11. 2 Queen Beds | NS, Shower

2 Queen Beds | NS, Shower
Midland
10.0 out of 10, Exceptional, (86 reviews)
"A quiet atmosphere really allowed us to rest well during our stay."
United States
Anonymous traveller
The price is CA $106
CA $121 total
includes taxes & fees
Nov 13 - Nov 14
2 Queen Beds | NS, Shower
A modern kitchen with grey cabinets, a black countertop, and a dishwasher.

12. Backyard & Game Room! Home in Heart of Midland

Backyard & Game Room! Home in Heart of Midland
3.0 star property
Midland
10.0 out of 10, Exceptional, (1 review)
"House was very clean, nice beds etc"
United States
Ashtyn
The price is CA $264
CA $695 total
includes taxes & fees
Nov 9 - Nov 10
Backyard & Game Room! Home in Heart of Midland
A swimming pool with a water feature, lounge chairs, and a building with multiple windows.

13. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Midland
10.0 out of 10, Exceptional, (87 reviews)
"Affordable stay close to many attractions,this place fit our needs perfectly without breaking the bank!"
United States
Anonymous traveller
The price is CA $106
CA $121 total
includes taxes & fees
Nov 13 - Nov 14
2 Queen Beds | Non-Smoking
A modern kitchen with grey cabinets, a black countertop, and a dishwasher.

14. Backyard & Game Room! Home in Heart of Midland

Backyard & Game Room! Home in Heart of Midland
Midland
10.0 out of 10, Exceptional, (1 review)
"Beautiful home. Very updated! Large bedrooms and Living areas!!! "
United States
Laurie S.
The price is CA $202
CA $670 total
includes taxes & fees
Nov 9 - Nov 10
Backyard & Game Room! Home in Heart of Midland
A swimming pool with a water feature, lounge chairs, and a building with multiple windows.

15. 2 Queen Beds | Non-Smoking, Kitchen, Shower

2 Queen Beds | Non-Smoking, Kitchen, Shower
Midland
10.0 out of 10, Exceptional, (82 reviews)
"Easy access to local spots made our stay simple and enjoyable."
United States
Anonymous traveller
The price is CA $125
CA $142 total
includes taxes & fees
Nov 13 - Nov 14
2 Queen Beds | Non-Smoking, Kitchen, Shower
A modern kitchen with white cabinetry, a marble island, stainless steel appliances, and a chandelier.

16. Modern & Spacious Stylish Comfort & Relaxation

Modern & Spacious Stylish Comfort & Relaxation
Stanton
The price is CA $369
CA $544 total
includes taxes & fees
Nov 9 - Nov 10
Modern & Spacious Stylish Comfort & Relaxation
A modern kitchen with a central island, built-in appliances, and a seating area with a sofa.

17. Relaxing RV w/ Outdoor Area

Relaxing RV w/ Outdoor Area
Midland
The price is CA $140
CA $250 total
includes taxes & fees
Nov 16 - Nov 17
Relaxing RV w/ Outdoor Area
A house with a fire feature in the front yard, a covered patio area, and a brick exterior.

18. 4-bedroom house in adorable Midland

4-bedroom house in adorable Midland
Midland
10.0 out of 10, Exceptional, (6 reviews)
"Great stay! The house was lovely, as pictured and very clean. Really nice neighborhood and good location. I would stay here again."
United States
Anonymous traveller
The price is CA $283
CA $486 total
includes taxes & fees
Nov 9 - Nov 10
4-bedroom house in adorable Midland
A modern living room with a green sofa, a round wooden coffee table, and a cityscape TV on the wall.

19. The Sage House • A Charming Wrst Texas Stay

The Sage House • A Charming Wrst Texas Stay
Midland
The price is CA $136
CA $311 total
includes taxes & fees
Dec 6 - Dec 7
The Sage House • A Charming Wrst Texas Stay
Interior

20. N BLVD-bbq pit, pong tbl, RO wkshop, 4bdrm-5beds

N BLVD-bbq pit, pong tbl, RO wkshop, 4bdrm-5beds
Midland
9.2 out of 10, Wonderful, (19 reviews)
"Pleasant."
United States
Matthew G.
The price is CA $313
CA $576 total
includes taxes & fees
Nov 30 - Dec 1
N BLVD-bbq pit, pong tbl, RO wkshop, 4bdrm-5beds
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.
View all properties

Find vacation rentals that suit your style

Cottage image
Cottages
Cottages
Apartment image
Apartments
Apartments

Top Greenwood Hotel Reviews

A row of mobile homes with front porches and steps leading to the entrance.
Custom Touch Village - Midland

Custom Touch Village - Midland

Custom Touch Village - Midland
Midland

10/10 Excellent

This place was better than expected. It was jusy what I needed this trip.
Canada
Virginia
Reviewed May 23, 2026
Custom Touch Village - Midland

Find out more about Greenwood

Everything you need to know about Greenwood 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 Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood vacation rentals we have selected for you start as low as CA $88 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 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 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 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 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 vacation rentals in Greenwood?

Yes, we give you a choice of vacation rentals near top sights in Greenwood, or you can go with a more secluded option if you want a relaxing place to stay.

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

Right At Home-Midland Groovy Times w/Pool: This vacation home rental outside of Greenwood is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Greenwood?

While you're exploring the area, Sibley Nature Center and I-20 Wildlife Preserve and Jenna Welch Nature Study Center are a couple of picturesque spots to get outside and enjoy nature. Permian Basin Petroleum Museum and The Horseshoe Midland County Multipurpose Facility are a couple of places you'll find in the larger area.

What are vacation rentals like in Greenwood?

Vacation rentals are privately owned properties you can book for several days or longer in Greenwood. Vacation rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips.