Resort
6 Guests
Hot Tub
Pool
Balcony/Terrace
Kitchen
US $248/Night
7 Nights - US $1,735
Bend Winter Rentals & Holiday Homes
Discover winter rentals Bend - We found 7261 exact matches
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Compare Winter Rental in Bend
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
Internet
Pet Friendly
Child Friendly
US $193/Night
7 Nights - US $1,352
US $328/Night
7 Nights - US $2,296
House
10.0(45 Reviews)
3 Bedrooms
8 Guests
Parking
Ocean View- Balcony/Terrace
View
US $461/Night
7 Nights - US $3,225
House
10.0(7 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Internet
US $290/Night
7 Nights - US $2,030
House
10.0(11 Reviews)
3 Bedrooms
8 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $468/Night
7 Nights - US $3,273
US $559/Night
7 Nights - US $3,913
House
10.0(8 Reviews)
3 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $608/Night
7 Nights - US $4,253
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
Skiing- Balcony/Terrace
US $531/Night
7 Nights - US $3,717
Cabin
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $971/Night
7 Nights - US $6,797
US $350/Night
7 Nights - US $2,450
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $297/Night
7 Nights - US $2,078
House
10.0(3 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Skiing
Air Conditioner
US $520/Night
7 Nights - US $3,639
House
9.8(11 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $600/Night
7 Nights - US $4,203
House
9.2(5 Reviews)
4 Bedrooms
13 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $682/Night
7 Nights - US $4,775
House
9.0(30 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
Spa- Ocean View
US $536/Night
7 Nights - US $3,749
House
9.0(6 Reviews)
3 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $382/Night
7 Nights - US $2,671
House
8.8(13 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $328/Night
7 Nights - US $2,298
House
8.0(16 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $425/Night
7 Nights - US $2,978
House
4.0(1 Review)
4 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $357/Night
7 Nights - US $2,499
House
10.0(98 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $343/Night
7 Nights - US $2,401
Cottage
10.0(53 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $255/Night
7 Nights - US $1,787
US $223/Night
7 Nights - US $1,558
Cottage
10.0(29 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $206/Night
7 Nights - US $1,441
About Bend Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 7261 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 Bend Winter Rentals
What are the top rated Winter Rentals in Bend?
There are a lot of options in Bend. If you plan on staying in the Bend area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Bend:
- Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
- Cozy log cabin with wrap-around porch, Hot tub Loft space, Washer & Dryer
- Great Downtown Location And House
- Amazing West Side - 2 King Suites - Walk Everywhere 8 Person Hot Tub
- BEAUTIFUL HOME OVERLOOKING THE RIVER-MINUTES TO IT ALL-UPDATED KITCHEN!
- Spacious and charming Craftsman retreat.
- Caldera Springs Aug. 16-23 AVAILABLE Happiness Is Just Around The Bend!
- Log cabin, private, hottub, sauna, spa, gardens, featured in national magazine.
- Enjoy Our Family Friendly Home In Tollgate
- Skyline Lodge, Gorgeous Setting, Walk to Downtown!
How much does it cost to rent a place to stay near Bend in the wintertime?
The average cost for winter rentals in Bend is $457 per night. Casai has a wide list of great winter places to stay near Bend that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Bend that allow pets?
Yes, here are the top cottage/chalet rentals in Bend that allow you to bring your pet or dog:
- Depoe Bay | Family Coastal Stay | Pool + Hot Tub | 2BR
- Bluebird Day - Casa Sol
- Wildflower Condo 54
- Beautiful family home, spacious living and only minutes from the beach.
See all pet-friendly vacation rentals in Bend on Casai.com
Do you have any winter rentals in Bend that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Bend to find what works for you.
Are there winter accommodations in Bend that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 7261 private swimming pools or indoor pools accommodations near Bend along with other great amenities.
Do any winter holiday rentals in Bend have hot tubs?
About 7261 holiday rentals in Bend boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Bend?
Yes, there are many luxury places to stay in Bend for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Bend with all the best amenities for your next trip.
