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Very Good

1 / 22 Winchester Cottage, 1933

From $150 / night help
Total guests,

Description from owner

Description from owner

Bedrooms 3 / Bathroom 1 / Sleeps 6 / House
Bedrooms: 3  Bathroom: 1   Sleeps: 6  Type: House

1 Full bath

Winchester Cottage, under old oaks in Carrabelle

Winchester Cottage was built as a wedding gift in 1933. It now sits under the canopy of 2 old oaks, on our main street but several blocks away from the main intersection at the harbor. It has 3 bedrooms, one bath (between 2 bedrooms), and is fully furnished and supplied with some bath and kitchen items. Compact yet roomy, doorways and walls have been widened and remodeled for openness and to create a light and airy feel.

Construction is tongue-and-groove pine, used for floors, walls and ceilings. The house sits up 2 easy steps, so that it is well-ventilated underneath. The large, breezy front porch runs the full width of the house and can seat a crowd for relaxing reading or socializing. Screen doors fore and aft allow nice air circulation in the temperate months if you prefer fresh air instead of AC, and an outdoor area with patio, deck and gas grill are ready for use.

Like to stroll for a little rejuvenation? The best walk in town starts right at the cottage. It's a "5K" for you serious walker/joggers, including sidewalks, harbor boardwalks and a shoreline drive. You go out for half the distance, then just return the same way, so you can make it as long or short as you want.

How about a driving tour? Carrabelle is at the heart of the Big Bend Scenic Byway, and the Cottage has a great brochure with all the info you might need. Whether coastal or forest, there are natural and historic/cultural things to see all day long!

SPECIAL OFFERS-- Rates drop, basically between Halloween and April Fool's Day. Check us out in the cool weather!

TripAdvisor property ID 4420140

More Property Details

Book this 3 bedroom house in Carrabelle today! A total of 6 people can sleep here comfortably.

Travelers are sharing their opinions on this property. It has an overall rating of 4.5/5 thanks to an average of 16 reviews.

Costs vary, with the average weekly rate as low as $800, depending on travel dates.

The owner responds to 90% of inquiries and last updated the property’s calendar Nov 16, 2018.

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About the owner

About the owner

Skip F.
Response rate:
Calendar last updated:
16 Nov 2018
Overall rating:

Languages spoken: English



Check in time:15:00, Check out time:10:00
If you have any questions about check-in or check-out times, please contact the owner/manager.
This rental can only be paid for online through FlipKey using your credit/debit card or PayPal (never by bank or wire transfer).
No smoking at this property
Cancellation policy
View Policy



Proximity to TripAdvisor's Top Carrabelle Attractions




  • Air conditioning
  • Ceiling Fans
  • Central heating
  • Clothes dryer
  • Hair dryer
  • Iron
  • Linen provided
  • Towels provided
  • Washing machine

Phone / Internet

  • Internet access
  • Wireless Internet

Property Features

  • Parking


  • Freezer
  • Fridge
  • Kettle
  • Microwave
  • Stove
  • Toaster


  • DVD player
  • Satellite TV
  • TV


  • Balcony or terrace
  • Deck
  • Grill
  • Patio
  • Private garden
  • Tennis in town


  • Children
  • Pets
  • Smoking not allowed


  • 1 Full bath


Reviews (16)

Very Good – based on 16 reviews Very Good
16 reviews

Very Good

“Six Weeks of Enjoying a Home away from Home!”

Reviewed 8 Apr 2014

Skip and Kathy are excellent innkeepers - shared their knowledge of Carrabelle, things to see and do, places to eat, and where to shop. The home was in perfect shape and had all the amenities you need. Winchester Cottage is such a delight and in a perfect location for walking and biking - lots to see and do. Loved everything about Winchester Cottage and especially the fact that they are dog friendly - this was extremely important to us.

Response from the owner Good, Good, Good--almost everything about this guest stay was good. When guests are inquisitive and appreciative, it makes this "job" of ours much more enjoyable. They treated the Cottage as if it was their home, and left it in great condition. We hope to see these guests again, and maybe even with a traveling companion--? Skip and Kathy

“Wonderful weekend getaway!”

Reviewed 16 Jan 2013

My husband and I just returned from a wonderful 3 day weekend at the Old Carrabelle Hotel. The old house has been charmingly restored, and the rooms are cozy and serene. The owners, Skip and Kathy, were attentive and helpful without smothering us. They were quick with restaurant recommendations and tips on things to see while respecting our privacy. This being an historic home, be mindful the windows are old, and street traffic is heard, at least from our room which overlooked Tallahassee St. But, don't let that discourage you from enjoying this hidden gem. Wifi is provided, and this was most helpful, since we had no cell service in town. Breakfast is provided in the form of a voucher to nearby 2 al's Cafe. I highly recommend the Cajun Seafood and cheese grits! I enjoyed it so much I had it all three mornings we were there. I'll be honest, if you aren't one to spend the entire day at the beach, your choices for entertainment are fairly limited in Carrabelle, but apalachicola is about 20 miles up the coast, and most of that trip is a 2 lane highway right on the water with a gorgeous view. All in all, I highly recommend the Old Carrabelle Hotel if you want a quiet getaway. We are already planning our next trip back, and have convinced some friends to come along. Thank you, Skip and Kathy, your hospitality was much appreciated, and we can't wait to return!

“The quintessential Old Florida stay.”

Reviewed 13 Jan 2013

Old Carabelle Hotel was everything we had hoped for in our stay in the "Forgotten Coast". The location was great, allowing excursions to many of the surrounding sites with minimal driving. The room was delightful and the accommodations homey and inviting. We felt right at home. Oh, by the way, the breakfasts that come with the stay are copious and yummy.

Response from the owner "Quintessential" and "copious" are words we don't hear much here on the coast. --But we know all about "homey" and "yummy" ! And we were very happy to see "everything we had hoped for". Skip and Kathy

Review 1-10 of 16

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