Apartment
10.0(272 Reviews)
2 Bedrooms
5 Guests
Parking
Balcony/Terrace
Kitchen
Internet
US $326/Night
7 Nights - US $2,282
Upper Loop/Upper Upper Loop Winter Rentals & Holiday Homes
Discover winter rentals Upper Loop/Upper Upper Loop - We found 1616 exact matches
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Compare Winter Rental in Upper Loop/Upper Upper Loop
10.0
Apartment
10.0(3 Reviews)
4 Bedrooms
10 Guests
Hot Tub
EV Charge Station- Parking
Skiing
US $211/Night
7 Nights - US $1,478
Condo
1 Bedroom
4 Guests
Child Friendly
US $239/Night
7 Nights - US $1,670
House
10.0(169 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $449/Night
7 Nights - US $3,141
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
Private Pool- Hot Tub
- Parking
Pool
US $492/Night
7 Nights - US $3,444
Cabin
10.0(165 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $358/Night
7 Nights - US $2,507
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Skiing
- Internet
Pet Friendly
US $1,389/Night
7 Nights - US $9,721
House
10.0(145 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $314/Night
7 Nights - US $2,199
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
US $601/Night
7 Nights - US $4,210
House
10.0(136 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $494/Night
7 Nights - US $3,461
House
10.0(1 Review)
1 Bedroom
8 Guests
- Private Pool
- Hot Tub
- EV Charge Station
- Parking
US $417/Night
7 Nights - US $2,921
House
10.0(122 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $447/Night
7 Nights - US $3,126
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Skiing
- Internet
Accessibility
US $708/Night
7 Nights - US $4,957
Condo
10.0(108 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Skiing
- Balcony/Terrace
US $441/Night
7 Nights - US $3,088
House
10.0(107 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $648/Night
7 Nights - US $4,536
House
10.0(86 Reviews)
1 Bedroom
14 Guests
- Hot Tub
- Parking
- Kitchen
- Internet
US $2,688/Night
7 Nights - US $18,819
House
10.0(84 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $362/Night
7 Nights - US $2,531
Condo
10.0(78 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $358/Night
7 Nights - US $2,507
Cabin
10.0(73 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $341/Night
7 Nights - US $2,388
Condo
10.0(63 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $642/Night
7 Nights - US $4,495
House
10.0(63 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
US $412/Night
7 Nights - US $2,885
House
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
View- Kitchen
US $311/Night
7 Nights - US $2,174
Condo
10.0(51 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Pool
- Spa
US $392/Night
7 Nights - US $2,744
Apartment
10.0(51 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $133/Night
7 Nights - US $931
About Upper Loop/Upper Upper Loop Winter Rental on Casai.nz
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 1616 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 Upper Loop/Upper Upper Loop Winter Rentals
What are the top rated Winter Rentals in Upper Loop/Upper Upper Loop?
There are a lot of options in Upper Loop/Upper Upper Loop. If you plan on staying in the Upper Loop/Upper Upper Loop area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Upper Loop/Upper Upper Loop:
- Charming & cozy house. Great location in town with relaxing patio and hot tub.
- Great Location, In town, amazing views from 275.00 night
- 4 BR Mountain Side Condo with Heated Pool and Hot Tub! Sleeps 9
- Bright w/High Ceilings & Deck - 2 Blocks from Elk in Quiet Corner of Town w/EV!
- Bella View
- Coal Creek In-town Retreat! 3BR/3 Full BAs - SLPS 8 - 2 blocks to Elk Ave!
- Spacious Delightful In-Town 6BD House, Guest BD/BA. July 2027 available
- Walk to Lifts, Newly Renovated, Mtn. Views, Fireplace, Hot Tub, Garage Access
- 3 Bedroom Apt in the Heart of Crested Butte!
- Big Condo. Incredible Views. Great 'Vibe'
How much does it cost to rent a place to stay near Upper Loop/Upper Upper Loop in the wintertime?
The average cost for winter rentals in Upper Loop/Upper Upper Loop is $661 per night. Casai has a wide list of great winter places to stay near Upper Loop/Upper Upper Loop that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Upper Loop/Upper Upper Loop that allow pets?
Yes, here are the top cottage/chalet rentals in Upper Loop/Upper Upper Loop that allow you to bring your pet or dog:
- Beautiful 2 Bedroom apartment in the heart of Crested Butte historic district.
- Teocalli Guest House
- NEW LISTING | Studio, Crested Butte - Pool, Hot Tub, 5min to Ski
- Downtown C B, Contemporary, Sunny 2BR, 2 BA, Stunning Views
See all pet-friendly vacation rentals in Upper Loop/Upper Upper Loop on Casai.nz
Do you have any winter rentals in Upper Loop/Upper Upper Loop that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Upper Loop/Upper Upper Loop to find what works for you.
Are there winter accommodations in Upper Loop/Upper Upper Loop that have indoor swimming pools?
As of 2026, the data from Casai.nz shows that there are over 1616 private swimming pools or indoor pools accommodations near Upper Loop/Upper Upper Loop along with other great amenities.
Do any winter holiday rentals in Upper Loop/Upper Upper Loop have hot tubs?
About 1616 holiday rentals in Upper Loop/Upper Upper Loop boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Upper Loop/Upper Upper Loop?
Yes, there are many luxury places to stay in Upper Loop/Upper Upper Loop for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Upper Loop/Upper Upper Loop with all the best amenities for your next trip.
