Cabin
10.0(12 Reviews)
2 Bedrooms
9 Guests
Hot Tub
Parking
Ocean View
Balcony/Terrace
R5,401/Night
7 Nights - R37,810
Gresham Winter Rentals & Holiday Homes
Discover winter rentals Gresham - We found 36 exact matches
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Compare Winter Rental in Gresham
10.0
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
Spa
Internet
R5,339/Night
7 Nights - R37,376
Hotel
8.6(706 Reviews)
Breakfast- Parking
Kitchen
Air Conditioner
R2,354/Night
7 Nights - R16,469
House
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,316/Night
7 Nights - R37,209
House
9.0(1 Review)
5 Bedrooms
10 Guests
- Parking
- Spa
- Balcony/Terrace
- Internet
R5,523/Night
7 Nights - R38,661
Cabin
10.0(7 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
View- Kitchen
R868/Night
7 Nights - R6,074
R5,992/Night
7 Nights - R41,948
House
9.4(13 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R3,659/Night
7 Nights - R25,613
Resort
10.0(1 Review)
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R2,619/Night
7 Nights - R18,338
House
10.0(28 Reviews)
3 Bedrooms
11 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,625/Night
7 Nights - R32,370
Cottage
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
Child Friendly
R7,250/Night
7 Nights - R50,758
House
10.0(1 Review)
4 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
R11,070/Night
7 Nights - R77,488
Cabin
9.8(288 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R4,207/Night
7 Nights - R29,450
Cottage
9.8(37 Reviews)
3 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
R6,284/Night
7 Nights - R43,983
House
9.8(10 Reviews)
3 Bedrooms
7 Guests
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
Security/Safety
R4,271/Night
7 Nights - R29,901
House
9.6(26 Reviews)
4 Bedrooms
14 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
R10,360/Night
7 Nights - R72,516
New
Cottage
9.6(14 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R7,948/Night
7 Nights - R55,630
House
9.6(11 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,779/Night
7 Nights - R47,454
House
9.6(5 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Ocean View
- View
R10,181/Night
7 Nights - R71,265
Cabin
9.0(21 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,484/Night
7 Nights - R38,377
House
8.8(5 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R9,838/Night
7 Nights - R68,862
Other
9.8(9 Reviews)
4 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,020/Night
7 Nights - R35,140
House
3 Bedrooms
8 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
R8,700/Night
7 Nights - R60,903
House
10.0(7 Reviews)
5 Bedrooms
14 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R6,701/Night
7 Nights - R46,903
About Gresham Winter Rental on Casai.co.za
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 36 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 Gresham Winter Rentals
What are the top rated Winter Rentals in Gresham?
There are a lot of options in Gresham. If you plan on staying in the Gresham area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Gresham:
- AmeriVu Inn & Suites
- Beautiful 20 acre ranch just outside of Shawano!
- Mader Haven Across from the Lake by RedAwning
- nWelcome to Mossy Back Lodge!nnCome stay up in this north woods hideaway!
- Valhalla Hillside Inn
- Shawano Vacation Rental: Close to Main Street!
- Lower unit of duplex on N. Main St. Shawano next to Huckleberry Harbor @ Channel
- 5 Bedroom Lake Condo w/Transportation to the NFL Draft 2025
- 4 Bedroom Condo w/Transportation to NFL Draft 2025
- 3 Bedroom Condo w/Transportation to the NFL Draft 2025
How much does it cost to rent a place to stay near Gresham in the wintertime?
The average cost for winter rentals in Gresham is $508 per night. Casai has a wide list of great winter places to stay near Gresham that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Gresham that allow pets?
Yes, here are the top cottage/chalet rentals in Gresham that allow you to bring your pet or dog:
- Adorable Lakefront Cabin with HOT TUB!
- Private Hot Tub: Riverfront Escape in Shawano
- Boarders Inn & Suites by Cobblestone Hotels - Shawano
- Riverfront - Trout Retreat - Firepit - Dog Friendly
See all pet-friendly vacation rentals in Gresham on Casai.co.za
Do you have any winter rentals in Gresham that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Gresham to find what works for you.
Are there winter accommodations in Gresham that have indoor swimming pools?
As of 2026, the data from Casai.co.za shows that there are over 36 private swimming pools or indoor pools accommodations near Gresham along with other great amenities.
Do any winter holiday rentals in Gresham have hot tubs?
About 36 holiday rentals in Gresham boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Gresham?
Yes, there are many luxury places to stay in Gresham for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Gresham with all the best amenities for your next trip.
