Cabin
10.0(591 Reviews)
2 Bedrooms
2 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $255/Night
7 Nights - US $1,788
USA Winter Rentals & Holiday Homes
Discover winter rentals USA - We found 1277682 exact matches
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Compare Winter Rental in USA
10.0
House
10.0(230 Reviews)
5 Bedrooms
14 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $110/Night
7 Nights - US $770
Apartment
1 Bedroom
4 Guests
Air Conditioner
Internet
Child Friendly
Bedding/Linens
US $196/Night
7 Nights - US $1,372
Apartment
10.0(543 Reviews)
2 Bedrooms
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $248/Night
7 Nights - US $1,736
Bed & Breakfast
10.0(99 Reviews)
12 Bedrooms
26 Guests
Private Beach- Oceanfront
- Hot Tub
Breakfast
US $337/Night
7 Nights - US $2,359
House
10.0(505 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
Pool- Ocean View
US $171/Night
7 Nights - US $1,198
House
10.0(54 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $355/Night
7 Nights - US $2,483
House
10.0(477 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $498/Night
7 Nights - US $3,486
Bed & Breakfast
10.0(53 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,120
Condo
10.0(471 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $340/Night
7 Nights - US $2,377
House
10.0(48 Reviews)
1 Bedroom
2 Guests
- Parking
- View
- Air Conditioner
- Internet
US $355/Night
7 Nights - US $2,482
House
10.0(452 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $268/Night
7 Nights - US $1,874
House
10.0(47 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $390/Night
7 Nights - US $2,730
House
10.0(422 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $356/Night
7 Nights - US $2,492
House
10.0(417 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $363/Night
7 Nights - US $2,544
House
10.0(411 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $236/Night
7 Nights - US $1,650
Condo
10.0(408 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $230/Night
7 Nights - US $1,609
Apartment
10.0(390 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $240/Night
7 Nights - US $1,679
Cottage
10.0(379 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $365/Night
7 Nights - US $2,552
Cottage
10.0(374 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $195/Night
7 Nights - US $1,367
House
10.0(367 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $257/Night
7 Nights - US $1,801
House
10.0(365 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $448/Night
7 Nights - US $3,136
Condo
10.0(359 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $248/Night
7 Nights - US $1,733
Villa
10.0(355 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $201/Night
7 Nights - US $1,405
About USA Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 1277682 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 USA Winter Rentals
What are the top rated Winter Rentals in USA?
There are a lot of options in USA. If you plan on staying in the USA area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in USA:
- The Rose Hotel
- Romantic Getaway in nearly 10 acres with Hot Tub
- River Rock Inn B&B - Adults Only
- 1800's Restored Log Cabin in Woods - 15 Min. Off Pa Turnpike
- Bluff Gardens Cabins
- Talkeetna Wilderness Lodge and Cabin Rentals
- Get cozy at Big Al's Poconos Creek House - Wireless DSL and Trout!
- 2 Queen Beds Non-Smoking
- Rocky Mountain Paradise
- Stunning Door County Cabin In The Woods, Wi-Fi, Firepit, Fireplace, Game Room
How much does it cost to rent a place to stay near USA in the wintertime?
The average cost for winter rentals in USA is $503 per night. Casai has a wide list of great winter places to stay near USA that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in USA that allow pets?
Yes, here are the top cottage/chalet rentals in USA that allow you to bring your pet or dog:
- Beautiful Riverfront Getaway in the Cascade Mountains
- Kings River Reflections
- SPI Waterfront Getaway - Wake up to Ocean Views
- Sweeping ocean views nestled in exquisite private garden
See all pet-friendly vacation rentals in USA on Casai.com
Do you have any winter rentals in USA that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in USA to find what works for you.
Are there winter accommodations in USA that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 1277682 private swimming pools or indoor pools accommodations near USA along with other great amenities.
Do any winter holiday rentals in USA have hot tubs?
About 1277682 holiday rentals in USA boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in USA?
Yes, there are many luxury places to stay in USA for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near USA with all the best amenities for your next trip.
