House
10.0(29 Reviews)
2 Bedrooms
5 Guests
Hot Tub
Parking
Balcony/Terrace
View
US $311/Night
7 Nights - US $2,174
La Pine Winter Rentals & Holiday Homes
Discover winter rentals La Pine - We found 97 exact matches
- Up-front pricing
- No markup
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Compare Winter Rental in La Pine
10.0
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
Internet
Pet Friendly
US $293/Night
7 Nights - US $2,048
US $197/Night
7 Nights - US $1,378
Cabin
10.0(25 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $338/Night
7 Nights - US $2,366
House
10.0(1 Review)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
Sports/Activities
Security/Safety
US $181/Night
7 Nights - US $1,267
Cottage
10.0(20 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $280/Night
7 Nights - US $1,962
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $188/Night
7 Nights - US $1,314
Cabin
10.0(15 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $285/Night
7 Nights - US $1,993
US $174/Night
7 Nights - US $1,215
Cabin
10.0(15 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $219/Night
7 Nights - US $1,533
House
9.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Internet
US $409/Night
7 Nights - US $2,860
Cottage
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $374/Night
7 Nights - US $2,615
House
8.7(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Spa
- Pet Friendly
- Security/Safety
US $169/Night
7 Nights - US $1,183
House
10.0(11 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $340/Night
7 Nights - US $2,383
Cabin
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $179/Night
7 Nights - US $1,252
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $143/Night
7 Nights - US $1,004
Cabin
9.6(4 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $219/Night
7 Nights - US $1,534
Cabin
9.4(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,939
Cabin
9.0(22 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $221/Night
7 Nights - US $1,548
House
8.8(29 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $141/Night
7 Nights - US $989
Cabin
8.4(10 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Pet Friendly
- Child Friendly
US $218/Night
7 Nights - US $1,525
New
House
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,116
Cabin
10.0(52 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $345/Night
7 Nights - US $2,415
House
10.0(45 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $377/Night
7 Nights - US $2,641
About La Pine Winter Rental on BedroomVillas
At BedroomVillas, we feature a wide range of listings for accommodations in La Pine, 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 La Pine, 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 La Pine and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About La Pine Winter Rentals
What are the top rated Winter Rentals in La Pine?
There are a lot of options in La Pine. If you plan on staying in the La Pine area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in La Pine:
- Modern A-Frame cabin w/hot tub close to Bend, Crater Lake, Mt Bachelor resort
- Cozy, relaxing house near La Pine State Park. Dogs ok!
- 'The Hub' La Pine Vacation Rental - Dog Friendly!
- Riverfront Log Cabin with Firepit in La Pine
- Peaceful Lapine 3 BR Getaway, sleeps up to 8
- Modern & Beautiful Cabin w/Hot Tub Serene location and comfortable stay
- Riverfront La Pine Luxurious Log Cabin
- A Perfect Location to Get Away
- Rustic and cozy log home, Room for the entire family.
- Private Riverfront Lodge w/Indoor Pool, Movie Theater, Hot Tub on Acreage
How much does it cost to rent a place to stay near La Pine in the wintertime?
The average cost for winter rentals in La Pine is $299 per night. BedroomVillas has a wide list of great winter places to stay near La Pine that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in La Pine that allow pets?
Yes, here are the top cottage/chalet rentals in La Pine that allow you to bring your pet or dog:
- Couples Retreat, hot tub, private!
- Family-friendly home with WiFi BBQ grill washer&dryer golf nearby
- DiamondStone Guest Lodges
- Executive cabin in the woods!
See all pet-friendly vacation rentals in La Pine on BedroomVillas
Do you have any winter rentals in La Pine that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in La Pine to find what works for you.
Are there winter accommodations in La Pine that have indoor swimming pools?
As of 2026, the data from BedroomVillas shows that there are over 97 private swimming pools or indoor pools accommodations near La Pine along with other great amenities.
Do any winter holiday rentals in La Pine have hot tubs?
About 97 holiday rentals in La Pine boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in La Pine?
Yes, there are many luxury places to stay in La Pine for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near La Pine with all the best amenities for your next trip.
