Cottage
1 Bedroom
2 Guests
Hot Tub
Parking
Ocean View
Balcony/Terrace
US $258/Night
7 Nights - US $1,807
Springfield Winter Rentals & Holiday Homes
Discover winter rentals Springfield - We found 19 exact matches
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Compare Winter Rental in Springfield
New
Cottage
2 Bedrooms
8 Guests
- Hot Tub
- Balcony/Terrace
Kitchen
Internet
US $255/Night
7 Nights - US $1,785
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $360/Night
7 Nights - US $2,519
Cottage
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,685
Cottage
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,685
New
Cottage
9.8(11 Reviews)
3 Bedrooms
9 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,824
House
8.0(2 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $220/Night
7 Nights - US $1,543
Cottage
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $420/Night
7 Nights - US $2,941
House
5 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $281/Night
7 Nights - US $1,969
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $273/Night
7 Nights - US $1,909
Apartment
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,235
US $116/Night
7 Nights - US $810
Apartment
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $210/Night
7 Nights - US $1,470
House
10.0(1 Review)
4 Bedrooms
10 Guests
Child Friendly
US $245/Night
7 Nights - US $1,712
House
8.0(2 Reviews)
3 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $202/Night
7 Nights - US $1,412
US $105/Night
7 Nights - US $736
Cabin
5.0(16 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
Pet Friendly- Child Friendly
US $148/Night
7 Nights - US $1,037
US $75/Night
7 Nights - US $523
Cabin
5 Bedrooms
10 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $95/Night
7 Nights - US $664
About Springfield Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 19 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 Springfield Winter Rentals
How much does it cost to rent a place to stay near Springfield in the wintertime?
The average cost for winter rentals in Springfield is $235 per night. Casai has a wide list of great winter places to stay near Springfield that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Springfield that allow pets?
Yes, here are the top cottage/chalet rentals in Springfield that allow you to bring your pet or dog:
- Enjoy the lovely setting of this romantic spot in nature.
- Lakefront Escape with hot tub and outdoor kitchen
- Lakefront Home on Washademoak Lake with Dock and 255 ft of Water Frontage.
- Copper Shore Lake House - Doncaster
See all pet-friendly vacation rentals in Springfield on Casai.com
Do you have any winter rentals in Springfield that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Springfield to find what works for you.
Are there winter accommodations in Springfield that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 19 private swimming pools or indoor pools accommodations near Springfield along with other great amenities.
Do any winter holiday rentals in Springfield have hot tubs?
About 19 holiday rentals in Springfield boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Springfield?
Yes, there are many luxury places to stay in Springfield for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Springfield with all the best amenities for your next trip.
