Bed & Breakfast
9.8(44 Reviews)
1 Bedroom
2 Guests
Hot Tub
Parking
Pool
Balcony/Terrace
AU $137/Night
7 Nights - AU $958
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
AU $117/Night
7 Nights - AU $820
AU $167/Night
7 Nights - AU $1,173
House
9.6(28 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
AU $599/Night
7 Nights - AU $4,194
AU $975/Night
7 Nights - AU $6,824
House
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $447/Night
7 Nights - AU $3,128
House
3 Bedrooms
8 Guests
- Parking
Internet
Child Friendly
Security/Safety
AU $441/Night
7 Nights - AU $3,090
House
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
AU $157/Night
7 Nights - AU $1,097
AU $560/Night
7 Nights - AU $3,917
House
10.0(5 Reviews)
7 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $802/Night
7 Nights - AU $5,612
AU $138/Night
7 Nights - AU $969
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $710/Night
7 Nights - AU $4,971
Villa
10.0(2 Reviews)
7 Bedrooms
20 Guests
Private Pool- Hot Tub
- Parking
- Pool
AU $1,591/Night
7 Nights - AU $11,135
House
9.8(12 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $543/Night
7 Nights - AU $3,800
Villa
9.8(9 Reviews)
7 Bedrooms
20 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,495/Night
7 Nights - AU $10,465
House
9.0(7 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
AU $570/Night
7 Nights - AU $3,986
House
8.8(20 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $742/Night
7 Nights - AU $5,195
House
8.0(1 Review)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $358/Night
7 Nights - AU $2,503
House
6.8(14 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $931/Night
7 Nights - AU $6,518
House
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $353/Night
7 Nights - AU $2,474
New
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $989/Night
7 Nights - AU $6,923
AU $144/Night
7 Nights - AU $1,008
House
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
AU $256/Night
7 Nights - AU $1,789
House
10.0(1 Review)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $900/Night
7 Nights - AU $6,300
About Gresham Winter Rental on BedroomVillas.com.au
At BedroomVillas, we feature a wide range of listings for accommodations in Gresham, OR that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Gresham, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Gresham and unlock even more amazing deals. Relax with BedroomVillas.
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 $374 per night. BedroomVillas.com.au 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 BedroomVillas.com.au
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 BedroomVillas.com.au 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.
