Title: Book the Best St. Augustine Historic District WINERY Hotels in 2026 | Expedia.ca

[St. Augustine Historic District Travel Guide](https://expedia.ca/St-Augustine-St-Augustine-Historic-District.dx6339215)[Vacation Rentals in St. Augustine](https://expedia.ca/St-Augustine-Vacation-Rentals.d6047864.Travel-Guide-VacationRentals)[Flights to St. Augustine](https://expedia.ca/Cheap-Flights-To-St-Augustine.d6047864.Travel-Guide-Flights)[Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)[St. Augustine Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-St-Augustine-Historic-District.d6339215.Car-Rental-Guide)[St. Augustine Historic District Vacations](https://expedia.ca/St-Augustine-Historic-District.d6339215.Destination-Travel-Guides)

![Cathedral Basilica of St. Augustine showing heritage elements and a church or cathedral](https://images.trvl-media.com/place/6069643/b82aecd8-c55b-4889-a7f1-c577ceee3148.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in St. Augustine Historic District, FL from CA $277

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## Check availability on St. Augustine Historic District Winery Hotels

Tonight

[Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=6339215&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=6339215&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6339215&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6339215&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for St. Augustine Historic District hotels with winery

![Exterior](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/12976fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/adf8ee4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/affccb1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casa Monica Resort & Spa, Autograph Collection

[](https://www.expedia.ca/St-Augustine-Hotels-Casa-Monica-Resort-Spa.h329630.Hotel-Information)

St. Augustine Historic District

9.0/10

Wonderful

(1002)

"Perfect location, very friendly staff, "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa

CA $397

CA $477 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/St-Augustine-Hotels-Casa-Monica-Resort-Spa.h329630.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/1c8f09af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/ec80d45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, Hot Tub ( (3, 4, 7))](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/0bb3946f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/00bca5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Agustin Inn

[](https://www.expedia.ca/St-Augustine-Hotels-Agustin-Inn.h17748908.Hotel-Information)

St. Augustine Historic District

9.2/10

Wonderful

(1002)

"Everything was just perfect!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Innokentiy

CA $268

CA $312 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/St-Augustine-Hotels-Agustin-Inn.h17748908.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/35b39f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 Queen Bed with Sofa bed, City View (Cadiz Suite) | Living area](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/d1af9b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed, City View (Patricia's Suite)](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/7614fda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/6c3369bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Victorian House Bed & Breakfast

[](https://www.expedia.ca/St-Augustine-Hotels-Victorian-House.h898873.Hotel-Information)

St. Augustine Historic District

9.4/10

Exceptional

(571)

"Great location, staff was friendly and helpful, room was nice, spacious and clean "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly

CA $285

CA $318 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/St-Augustine-Hotels-Victorian-House.h898873.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/ccfc348c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 King Bed | Private kitchenette](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/f71702d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/a6574d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/da1d031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carriage Way Inn

[](https://www.expedia.ca/St-Augustine-Hotels-Carriage-Way-Bed-Breakfast.h2345615.Hotel-Information)

St. Augustine Historic District

9.6/10

Exceptional

(664)

"Great staff and great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsay

CA $374

CA $418 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/St-Augustine-Hotels-Carriage-Way-Bed-Breakfast.h2345615.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/e0f1a250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/ac28c793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/2b123828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Country French #7 | Balcony](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/d4724c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Kenwood Inn

[](https://www.expedia.ca/St-Augustine-Hotels-The-Kenwood-Inn.h36682652.Hotel-Information)

St. Augustine Historic District

9.6/10

Exceptional

(332)

"Breakfast was excellent and unique. The property was great. The staff was especially friendly and efficient."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Suzanne

[](https://www.expedia.ca/St-Augustine-Hotels-The-Kenwood-Inn.h36682652.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956444/aab56b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956444/w818h1080x559y0-3548a7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956444/w1847h1170x1y0-9cae0d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956444/w875h982x523y50-3650ac38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1880 Victorian In Heart Of Downtown 

[](https://www.expedia.ca/St-Augustine-Hotels-1880-Victorian-In-Heart-Of-Downtown.h18956444.Hotel-Information)

St. Augustine Historic District

9.8/10

Exceptional

(198)

"Fantastic location and comfortable stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Harolyn S.

CA $169

CA $316 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/St-Augustine-Hotels-1880-Victorian-In-Heart-Of-Downtown.h18956444.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119145/75acd245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119145/0ad09fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119145/633e2e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33120000/33119200/33119145/e960dd0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown Hideaway, studio accommodations, in the heart of the Historic District

[](https://www.expedia.ca/St-Augustine-Hotels-Downtown-Hideaway.h33119145.Hotel-Information)

St. Augustine Historic District

9.6/10

Exceptional

(389)

"Absolutely love staying here. Great location and Very clean rooms. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tracy K.

CA $161

CA $277 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/St-Augustine-Hotels-Downtown-Hideaway.h33119145.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/4047bae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/8989cc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/3396c695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/325e3f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heart of Historic District! Rooftop with Fire Pit, Park and Walk Everywhere, $300 in Free Tickets!

[](https://www.expedia.ca/St-Augustine-Hotels-Rooftop-WFirepit.h90795726.Hotel-Information)

St. Augustine Historic District

10/10

Exceptional

(90)

"Exceeded our expectations. Great place and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

patrick

CA $221

CA $638 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/St-Augustine-Hotels-Rooftop-WFirepit.h90795726.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/9528789e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/c3020d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/ccc8d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/9e231874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heart of Historic Downtown, Renovated, Park and Walk to Attractions, Balcony, $300 in Free Tickets!

[](https://www.expedia.ca/St-Augustine-Hotels-Heart-Of-Historic-Downtown.h112947161.Hotel-Information)

St. Augustine Historic District

10/10

Exceptional

(10)

"Property was well listed and described. In the heart of the historic district and in walking distance to all main tourist sites. Very clean and well stocked. As stated, there are restaurants and bars that are open and play music until midnight on the weekend so it can be loud until then. Overall an amazing place to stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hailee B.

CA $305

CA $747 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/St-Augustine-Hotels-Heart-Of-Historic-Downtown.h112947161.Hotel-Information)

![Apartment (62 Hypolita Carriage House) | Exterior](https://images.trvl-media.com/lodging/92000000/91410000/91409600/91409557/fa82fbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (62 Hypolita Carriage House) | Exterior](https://images.trvl-media.com/lodging/92000000/91410000/91409600/91409557/50ae37ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (62 Hypolita Carriage House) | Exterior](https://images.trvl-media.com/lodging/92000000/91410000/91409600/91409557/a0ec83b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (62 Hypolita Carriage House) | Exterior](https://images.trvl-media.com/lodging/92000000/91410000/91409600/91409557/888f5cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 62 Hypolita Carriage House

[](https://www.expedia.ca/St-Augustine-Hotels-62-Hypolita-Carriage-House.h91409557.Hotel-Information)

St. Augustine Historic District

CA $287

CA $615 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/St-Augustine-Hotels-62-Hypolita-Carriage-House.h91409557.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&regionId=6339215&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top St. Augustine Historic District Hotel Reviews

![Casa Monica Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7_y.jpg)

### Casa Monica Resort & Spa, Autograph Collection

10/10 Excellent

"This hotel first class all the way.... Pick something like: Staff, location, food and drinks, cleanliness, facilities and you have it all....choose Casa Monica when you think of St. Augustine..."

[](https://expedia.ca/St-Augustine-Hotels-Casa-Monica-Resort-Spa.h329630.Hotel-Information)

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- [Hotels with an Indoor Pool in St. Augustine ](https://www.expedia.ca/St-Augustine-Hotels-Hotels-With-Indoor-Pool.0-0-d6047864-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
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- [Hotels with Waterslides in St. Augustine ](https://www.expedia.ca/St-Augustine-Hotels-Hotels-With-Waterslides.0-0-d6047864-tHotelswithWaterslides.Travel-Guide-Filter-Hotels)
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- [Houseboats in St. Augustine ](https://www.expedia.ca/St-Augustine-Houseboats.d6047864-aaHouseboats.Travel-Guide-Accommodation)
- [Inns in St. Augustine ](https://www.expedia.ca/St-Augustine-Inns.d6047864-aaInns.Travel-Guide-Accommodation)
- [Motels in St. Augustine ](https://www.expedia.ca/St-Augustine-Motels.d6047864-aaMotels.Travel-Guide-Accommodation)
- [Hotels near St. Augustine Municipal Marina ](https://www.expedia.ca/St-Augustine-Municipal-Marina-Hotels.0-l553248621563220464-0.Travel-Guide-Filter-Hotels)
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- [Villas in St. Augustine ](https://www.expedia.ca/St-Augustine-Villas.d6047864-aaVillas.Travel-Guide-Accommodation)
- [Hotels near St. George Street ](https://www.expedia.ca/St-George-Street-Hotels.0-l6339216-0.Travel-Guide-Filter-Hotels)
- [Hotels near Villa Zorayda Museum ](https://www.expedia.ca/Villa-Zorayda-Museum-Hotels.0-l553248621533116284-0.Travel-Guide-Filter-Hotels)

- [Flights to St. Augustine ](https://www.expedia.ca/Cheap-Flights-To-St-Augustine.d6047864.Travel-Guide-Flights)
- [Flights to St. Johns County ](https://www.expedia.ca/Destinations-In-St-Johns-County.d553248635083898088.Flight-Destinations)
- [Flights from St. Augustine ](https://www.expedia.ca/lp/flights/6047864/flights-from-st-augustine)

- [Cathedral Basilica of St. Augustine ](https://www.expedia.ca/Cathedral-Basilica-Of-St-Augustine-St-Augustine-Historic-District.d6069643.Vacation-Attraction)
- [Flagler College ](https://www.expedia.ca/Flagler-College-Downtown-Historic-District.d6127768.Vacation-Attraction)
- [Ponce de Leon Hotel ](https://www.expedia.ca/Ponce-De-Leon-Hotel-St-Augustine-Historic-District.d553248621533116288.Vacation-Attraction)
- [St. Augustine Vacations ](https://www.expedia.ca/St-Augustine.d6047864.Destination-Travel-Guides)
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- [St. George Street ](https://www.expedia.ca/St-George-Street-Downtown-Historic-District.d6339216.Vacation-Attraction)

- [Car rental St. Augustine ](https://www.expedia.ca/Car-Rentals-In-St-Augustine.d6047864.Car-Rental-Guide)
- [Enterprise Rental Cars in St. Augustine ](https://www.expedia.ca/Enterprise-Car-Rentals-In-St-Augustine.d6047864-c15.Car-Rental-Guide-Suppliers)
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- [St. Augustine Vacation Rentals ](https://www.expedia.ca/St-Augustine-Vacation-Rentals.d6047864.Travel-Guide-VacationRentals)

- [Things to do in St. Augustine ](https://www.expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

- [Book Hotels in St. Augustine Historic District on Expedia.com ](https://www.expedia.com/St-Augustine-Historic-District-St-Augustine-Hotels-Winery-Hotel.0-n6339215-0-tWineryHotel.Travel-Guide-Filter-Hotels)