Plan your trip

A large tree with extensive moss and Spanish moss hanging from its branches.

Greenwood Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

    View in a map

    Our top choices for Greenwood vacation rentals

    1. Charming cabin close to Malmaison Wildlife Refuge, and McIntyre Scatters

    A covered porch with a cushioned bench and decorative pillows, a wooden railing, and a clear view of the surrounding landscape.

    2. Charming family retreat

    A living room with a fireplace, a television, and a sofa.

    3. The Charming Southerner

    A dining area with a long wooden table, multiple chairs, a white door, and a small plant on the wall.

    4. 2 Queen Bed | Ruleville MS

    A brick wall with a window and a shelf.

    5. The Bleu- Furnished Home Near MVSU for Work Crews/Extended Stays

    A dining area with a black table and chairs, patterned floor tiles, a potted plant, and a painting on the wall.

    6. Grenada MS | King Bed

    A dining area with round wooden tables and chairs, a television, and potted plants.

    7. King Bed | Ruleville MS

    A brick wall with a window and a shelf.

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

    A wooden cabin with a balcony, surrounded by trees.

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

    A living room with a sectional sofa, armchairs, a coffee table, and a dining area with a table and chairs.

    10. Grenada MS | King Bed Smoking

    A dining area with round wooden tables and chairs, a television, and potted plants.

    11. King Bed Accessible|Grenada MS

    A spacious living room with a large flat-screen TV, comfortable seating, and a Christmas tree.

    12. Magnolia State Winter Escape – Beautiful 3BR Family Home

    A living room with two black leather sofas, a patterned rug, and a dark wooden cabinet.

    13. Charming 3-bedroom barn in quaint Winona with AC

    A wooden door with two glass panels, a wreath on each, and a sign reading "1418B".

    14. The Crappie-2 bedroom cabin with spacious parking

    77f49a8d

    15. The Get-A-Way at Grenada lake

    A wooden deck with a view of a lake, a grill, and a grill cover.

    16. The most unique getaway experience in North Mississippi!

    IMG_1772

    17. Dogwoods-2 bedroom cabin with spacious parking

    fe118567

    18. Grenada MS |2 Queen Bed

    A dining area with round wooden tables and chairs, a television, and potted plants.

    19. 2 Queen Bed|Smk|Grenada MS

    A dining area with round wooden tables and chairs, a television, and potted plants.

    20. Charming ranch style log cabin with AC in scenic Winona

    A cozy cabin interior with a wooden ceiling, a ceiling fan, a kitchen area with a refrigerator and stove, a dining area with a table and chairs, and a living room with a couch.

    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

    Cabins

    Apartments

    Cottages

    Condos

    Top Greenwood Hotel Reviews

    Hampton Inn & Suites Grenada

    A hotel lobby with a reception desk, seating area, and a bar.

    Holiday Inn Express & Suites - Greenwood by IHG

    A buffet with various food items, including omelets and other dishes, arranged in metal serving trays.

    Holiday Inn Express & Suites Grenada by IHG

    A building entrance with a central door, flanked by columns, and a tiled floor.

    Hampton Inn Greenwood

    A modern living room with two grey sofas, a coffee table, and a decorative wall unit with a vase.

    SureStay Plus Hotel by Best Western Greenwood

    An indoor swimming pool with a brick column, a staircase, and a balcony with chairs.

    Holiday Inn Express and Suites Winona North by IHG

    A Holiday Inn Express hotel with a covered entrance, a brick facade, and a clear sky.

    Americas Best Value Inn Winona

    A hotel room with a large bed, a desk with a computer, a chair, and a television.

    Comfort Inn & Suites Grenada

    A spacious lobby with a wooden floor, red armchairs, a coffee station, and a large window.

    Econo Lodge Grenada

    A hotel room with a bed, a sofa, a small table, a desk, a lamp, a painting on the wall, and a mirror.

    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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $50 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 offer vacation rentals in Greenwood close to The Mississippi Gift Company, or you can go with a more remote option if you want a relaxing stay. Our travelers say Greenwood has a good selection of restaurants. Make sure you have time to check out the cafes and shopping during your trip.

    What's the top vacation rental that Greenwood has to offer?

    Charming family retreat : This highly rated vacation home rental in Greenwood offers a garden, a barbecue grill, 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 you can cook with friends or family. Some other top choices in Greenwood are Homey Greenwood Getaway w/ Patio & Backyard and Family-Friendly Retreat w/ Fireplaces in Greenwood.

    How many vacation rentals are there in Greenwood?

    Choose from 6 Expedia vacation rentals in Greenwood for a memorable vacation.

    What can I see and do in Greenwood?

    Fort Pemberton Memorial Park and Veterans Memorial 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 Florewood State Park are other places to visit while you're in town.

    What are vacation rentals like in Greenwood?

    Vacation rentals are privately owned properties you can reserve for a couple days or more in Greenwood. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.

    Explore a world of travel with Expedia