Cottage
10.0(69 Reviews)
3 Bedrooms
6 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $352/Night
7 Nights - CA $2,463
Greenup Winter Rentals & Holiday Homes
Discover winter rentals Greenup - We found 7 exact matches
- Up-front pricing
- No markup
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Compare Winter Rental in Greenup
10.0
House
2 Bedrooms
6 Guests
- Parking
Internet
Pet Friendly
Child Friendly
CA $247/Night
7 Nights - CA $1,726
House
9.2(17 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $272/Night
7 Nights - CA $1,907
Hotel
6.4(169 Reviews)
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $81/Night
7 Nights - CA $565
Other
10.0(31 Reviews)
4 Bedrooms
8 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
CA $552/Night
7 Nights - CA $3,861
Other
10.0(1 Review)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $267/Night
7 Nights - CA $1,869
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $254/Night
7 Nights - CA $1,778
People Visiting Greenup Also Like
Apartment
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $228/Night
7 Nights - CA $1,594
House
10.0(1 Review)
3 Bedrooms
7 Guests
- Parking
- Internet
- Pet Friendly
Sports/Activities
CA $278/Night
7 Nights - CA $1,949
Cottage
10.0(1 Review)
1 Bedroom
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $334/Night
7 Nights - CA $2,335
House
10.0(77 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $198/Night
7 Nights - CA $1,384
CA $281/Night
7 Nights - CA $1,968
CA $163/Night
7 Nights - CA $1,142
House
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $339/Night
7 Nights - CA $2,375
Apartment
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Pet Friendly
- Child Friendly
CA $175/Night
7 Nights - CA $1,227
CA $102/Night
7 Nights - CA $716
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Laundry
Bedding/Linens
CA $221/Night
7 Nights - CA $1,548
CA $179/Night
7 Nights - CA $1,255
Hotel
7.6(944 Reviews)
Breakfast- Parking
- Kitchen
- Air Conditioner
CA $101/Night
7 Nights - CA $705
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
CA $290/Night
7 Nights - CA $2,028
CA $88/Night
7 Nights - CA $618
House
9.8(45 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $333/Night
7 Nights - CA $2,328
New
House
8.4(16 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $398/Night
7 Nights - CA $2,786
House
2 Bedrooms
- Air Conditioner
- Internet
- Child Friendly
- Laundry
CA $370/Night
7 Nights - CA $2,587
Apartment
1 Bedroom
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
CA $170/Night
7 Nights - CA $1,189
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $222/Night
7 Nights - CA $1,558
House
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $247/Night
7 Nights - CA $1,730
House
9.8(40 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $282/Night
7 Nights - CA $1,975
CA $151/Night
7 Nights - CA $1,060
About Greenup Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 7 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Greenup Winter Rentals
What are the top rated Winter Rentals in Greenup?
There are a lot of options in Greenup. If you plan on staying in the Greenup area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Greenup:
- Vintage Charmer on Main Street
- Country House
- Townhouse in Greenup, IL
- Family Friendly Cottage in the Countryside
- Mins to Local Attractions: Pet Friendly w/Yard!
- Mins to Local Attractions: Pet Friendly w/Yard!
- Park View Place 4 Blocks From the World's Biggest
- Eighteen-Ninety Sleepover
- Eighteen-Ninety Sleepover
- Mins to Local Attractions: Pet Friendly w/Yard!
How much does it cost to rent a place to stay near Greenup in the wintertime?
The average cost for winter rentals in Greenup is $206 per night. Casai has a wide list of great winter places to stay near Greenup that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Greenup that allow pets?
Yes, here are the top cottage/chalet rentals in Greenup that allow you to bring your pet or dog:
- Cottage By The Park Home of The Big Things
- Jewett Winter Escape: Trails, Casey & Fire Pit
- Jewett Winter Escape: Trails, Casey & Fire Pit
- Days Inn & Suites by Wyndham Casey
- Montrose Studio Getaway w/Covered Patio
- Mins to Local Attractions: Pet Friendly w/Yard!
- Mins to Local Attractions: Pet Friendly w/Yard!
- Vintage Charmer on Main Street
See all pet-friendly vacation rentals in Greenup on Casai.ca
Do you have any winter rentals in Greenup that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Greenup to find what works for you.
Are there winter accommodations in Greenup that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 7 private swimming pools or indoor pools accommodations near Greenup along with other great amenities.
Do any winter holiday rentals in Greenup have hot tubs?
About 7 holiday rentals in Greenup boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Greenup?
Yes, there are many luxury places to stay in Greenup for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Greenup with all the best amenities for your next trip.
