Bed & Breakfast
9.8(44 Reviews)
1 Bedroom
2 Guests
Hot Tub
Parking
Pool
Balcony/Terrace
R1,590/Night
7 Nights - R11,126
Gresham Winter Rentals & Holiday Homes
Discover winter rentals Gresham - We found 41 exact matches
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Compare Winter Rental in Gresham
9.8
House
9.7(74 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
R1,360/Night
7 Nights - R9,527
R1,946/Night
7 Nights - R13,624
House
9.6(28 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
R6,963/Night
7 Nights - R48,733
R11,327/Night
7 Nights - R79,295
House
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R5,191/Night
7 Nights - R36,341
House
3 Bedrooms
8 Guests
- Parking
Internet
Child Friendly
Security/Safety
R5,130/Night
7 Nights - R35,908
House
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
R1,922/Night
7 Nights - R13,457
R6,502/Night
7 Nights - R45,518
House
10.0(5 Reviews)
7 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R9,314/Night
7 Nights - R65,205
R1,608/Night
7 Nights - R11,259
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,251/Night
7 Nights - R57,760
Villa
10.0(2 Reviews)
7 Bedrooms
20 Guests
Private Pool- Hot Tub
- Parking
- Pool
R18,617/Night
7 Nights - R130,326
House
9.8(12 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R6,307/Night
7 Nights - R44,153
Villa
9.8(8 Reviews)
7 Bedrooms
20 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R18,962/Night
7 Nights - R132,741
House
9.0(7 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R6,618/Night
7 Nights - R46,318
House
8.8(20 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,622/Night
7 Nights - R60,358
House
8.0(1 Review)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
R4,155/Night
7 Nights - R29,080
House
6.8(14 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R10,820/Night
7 Nights - R75,731
House
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,107/Night
7 Nights - R28,747
New
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R11,492/Night
7 Nights - R80,444
R1,673/Night
7 Nights - R11,709
House
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R2,969/Night
7 Nights - R20,786
House
10.0(1 Review)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R10,456/Night
7 Nights - R73,199
About Gresham Winter Rental on Casai.co.za
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 41 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:
- HOT TUB AT THE BACK YARD.
- Great Deals on Summer Stays!
- Peaceful Gresham Home w/Grill: 2 Mi to Downtown
- Bridging the Gorge & City: Your Cozy Home!
- Hot Tub|Pool Table|Fire Pit| SpringWater Retreat
- Gresham Golf Course - Ranch Style With Swimming Pool
- Entire 2,000 sqft with washer, dryer.
- Single-story townhome with 2 patios, outdoor pool & great location near Gorge
- Gut Renovated Modern Ranch House With Golf Course
- Portland Vacation Rental w/Fireplace - Near Parks
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 $376 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:
- Private level of the house with SPA near PDX and famous waterfalls and mountain!
- Private level of the house with SPA
- Quality Inn
- #StayinMyDistrict Gorge-Mt Hood
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 41 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 41 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.
