The Winchester Cottage

An Authentic Coastal Cottage

The Cottage in CarrabelleDiscover one of the most unique and charming Carrabelle vacation rentals: Winchester Cottage, owned by The Old Carrabelle Hotel. Nestled under majestic oaks just up the street from the hotel, this one-of-a-kind cottage offers ultimate privacy with modern conveniences and historical charm.

One of the few remaining authentic Florida coastal cottages, Winchester Cottage is 1933 vintage. Just five blocks from Carrabelle Harbor and two miles from the beach, this picturesque cottage stands apart from other Carrabelle FL vacation rentals.

In the 1930’s, a local builder constructed this house for his daughter Emma and presented it to her as a wedding present. Miss Emma and Mr. Emmitt Winchester lived out their lives here, and there are relatives still in town, down to the great-grand level.

Miss Emma and Emmitt

Winchester Cottage is constructed from 1930s tongue-and-groove heart pine, used throughout the home’s floors, walls and ceilings. The house sits up two easy steps, so that it is well-ventilated underneath. Running the full width of the house, the large, breezy front porch is perfect for entertaining a crowd, reading or relaxing. Screen doors at the front and back of the cottage allow for nice air circulation for those who prefer fresh air to A/C. This recently remodeled, fully-furnished three-bedroom, one-bathroom house includes cable TV, WiFi and ample parking.

Sidewalks are available in nearly all downtown areas, which are easily accessible from the cottage. The property sits at the start of one of the best walks in the area. This three-mile course takes you down to and around Carrabelle Harbor and then along a lane between a Florida swamp and the Gulf of Mexico.

Ready for a bite to eat? There are half a dozen restaurants in Carrabelle, and even more dining options across the Forgotten Coast.

The Big Bend Scenic Byway, which runs along our coast, recently was named a U.S. Scenic Highway. Winding for more than 200 miles through coastal and forest roads, The Big Bend Scenic Byway is bursting with wildlife viewing opportunities—and your base at Winchester Cottage is the perfect launch point for exploration.

If you’re searching for the most unique Vacation Rental Carrabelle FL has to offer, look no further than Winchester Cottage.

Nightly (3-night minimum)
Cool Months: $525
Warm Months: $575

Cool Months: $700
Warm Months: $900

Cool Months: $2,000
Warm Months: $2,500

Please contact us by text or phone 850-528-3983 for a length of stay quote not listed above.

Check price and availability

Check price and availability for the Winchester Cottage

Check-In Date:

Check-Out Date:






Enter your details

Cancellation Policy

Hotel rooms: 48 hours advance notice. If less than 48 hours, we will refund your room charges if we are able to rent the room. On special event weekends and major holidays, we require one week notice.

Winchester Cottage vacation rental: 2 weeks notice. As always, any time we are able to re-rent your time slot, your refund will be complete.

Payment Policy

Hotel rooms: We will charge your room while you are here.

Winchester Cottage: 20% with reservation, balance 2 weeks before arrival. We will contact you to arrange the 20% deposit, then the balance will be charged 2 weeks before check-in.


Reservation summary

Thanks for your reservation! We have just sent you a confirmation email at with the following details:

Check-In Date: - Change
Check-Out Date: - Change
Number of nights:
Accommodation: - Change

Accommodation price: $
Options price: -$
Coupon discount amount: $

Total price (including tax): $

Accept our policies for this reservation

Please enter your credit cards details below.



Safe and secure payments SSL encrypted


Please double check your reservation details before clicking on "Book Now". The Hotel must confirm all reservations, and some major holidays require a 2-night minimum. If your reservation is for TONIGHT, it must be received before 3 PM. Thank you.