Connecticut Winter Rental
Villa
10.0(116 Reviews)
2 Bedrooms
1 Bath
4 Guests
1300 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
US $274/Night
7 Nights - US $1,916
House
10.0(17 Reviews)
3 Bedrooms
3 Baths
8 Guests
1550 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
View
US $1,018/Night
7 Nights - US $7,126
Bed & Breakfast
10.0(92 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Parking
US $611/Night
7 Nights - US $4,274
Cottage
10.0(93 Reviews)
2 Bedrooms
1 Bath
4 Guests
812 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $196/Night
7 Nights - US $1,369
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1399.31 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $497/Night
7 Nights - US $3,477
House
10.0(89 Reviews)
2 Bedrooms
1 Bath
4 Guests
798 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $431/Night
7 Nights - US $3,019
Apartment
10.0(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
2098.96 ft²
Private Beach- Oceanfront
- Ocean View
- View
US $703/Night
7 Nights - US $4,921
House
10.0(77 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $383/Night
7 Nights - US $2,683
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1097.92 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $479/Night
7 Nights - US $3,354
House
10.0(75 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $433/Night
7 Nights - US $3,032
House
10.0(3 Reviews)
1 Bedroom
2 Baths
7 Guests
1840.63 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Pet Friendly
US $437/Night
7 Nights - US $3,057
House
10.0(70 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $362/Night
7 Nights - US $2,536
Why Choose Rent By Owner for your Connecticut Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Connecticut
How to Book Your Connecticut Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Connecticut
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Connecticut, CT
New Haven
New London County
Mystic - New London
New Haven County
Hartford
Hartford County
Fairfield County
Gold Coast
Stamford
Litchfield County
Middlesex County
Old Saybrook
Connecticut Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Connecticut?
There are a lot of options in Connecticut. If you plan on staying in the Connecticut area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Connecticut:
- Romantic Guesthouse in Historic Downtown Waterfront District!
- Mystic Home perfect for families- Easy walk to downtown. .
- Charming Carriage House - Beach - Ocean Views - Fireplace
- Charming Historic House in Downtown Mystic
- Go Jump in the Lake!
- Secluded Waterfront Location With Dock
- Classic Lake House w/private waterfront, 4 steps to water, FirePit/Kayaks/canoe
- The Hemingway Carriage House - Romantic & Private Downtown Mystic Getaway
- Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
- Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
2. How many Winter Rentals are available in Connecticut?
Currently, the total number of properties listed by RBO in 2026 is over 3137 in the Connecticut area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Connecticut.
More Rentals You May Like Near Connecticut
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
2195.84 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $301/Night
7 Nights - US $2,107
Apartment
10.0(66 Reviews)
1 Bedroom
1 Bath
2 Guests
625 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $187/Night
7 Nights - US $1,308
Cottage
10.0(57 Reviews)
2 Bedrooms
1 Bath
6 Guests
1350 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $380/Night
7 Nights - US $2,657
Cottage
10.0(50 Reviews)
2 Bedrooms
1 Bath
6 Guests
624 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $293/Night
7 Nights - US $2,053
Cottage
10.0(48 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $334/Night
7 Nights - US $2,335
House
10.0(46 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $640/Night
7 Nights - US $4,482
Cottage
10.0(42 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $538/Night
7 Nights - US $3,763
Cottage
10.0(35 Reviews)
2 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $419/Night
7 Nights - US $2,933
Cabin
10.0(34 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $281/Night
7 Nights - US $1,964
Cottage
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $296/Night
7 Nights - US $2,071
Cottage
10.0(28 Reviews)
2 Bedrooms
1 Bath
2 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $211/Night
7 Nights - US $1,480
House
10.0(26 Reviews)
2 Bedrooms
1 Bath
6 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $799/Night
7 Nights - US $5,593
