66+ Vacation Rentals Near Pomona Winery |
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  4. Pomona Winery

Sailings Canada - Vacation Rentals in Pomona Winery

Big Sky Cabin! Hot Tub! On the Wine Trail! Fire Pit! Pool Table! Large Deck!n From US $422
         

9.8 (177 Reviews)
Cabin
Big Sky Cabin! Hot Tub! On the Wine Trail! Fire Pit! Pool Table! Large Deck!n
  • Air Conditioner
  • Parking
  • TV

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Peachbarn Winery & Cafe From US $90
         

|
7.0 (3 Reviews)
House
Peachbarn Winery & Cafe
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet Friendly! Countryside Couples Stay in Illinois From US $238
         

New
Cottage
Pet Friendly! Countryside Couples Stay in Illinois
  • Pet Friendly
  • TV
  • Security/Safety

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Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross From US $260
         

10.0 (70 Reviews)
Cabin
Relaxing Unique Cave Creek Cabin 2 in Shawnee near Alto Pass and Bald Knob Cross
  • Air Conditioner
  • Parking
  • TV

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The Bitty House From US $115
         

|
10.0 (2 Reviews)
House
The Bitty House
  • Parking
  • Pet Friendly
  • Child Friendly

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Secluded Cabin. Art. Fast WiFi. Fireplace. New Kitchen From US $230
         

10.0 (91 Reviews)
Cabin
Secluded Cabin. Art. Fast WiFi. Fireplace. New Kitchen
  • Air Conditioner
  • Parking
  • TV

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Great Shawnee Wine Trail Cabin in Relaxing Setting From US $260
         

10.0 (61 Reviews)
Cabin
Great Shawnee Wine Trail Cabin in Relaxing Setting
  • Air Conditioner
  • Parking
  • TV

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Pet Friendly! Countryside Couples Stay in Illinois From US $145
         

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8.7 (3 Reviews)
House
Pet Friendly! Countryside Couples Stay in Illinois
  • Parking
  • Pet Friendly
  • Security/Safety

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Lakefront, Pet-Friendly 1BR w/Porch & Fire Pit From US $263
         

New
Cabin
Lakefront, Pet-Friendly 1BR w/Porch & Fire Pit
  • Pet Friendly
  • TV
  • Balcony/Terrace

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On the Shawnee Wine Trail From US $176
         

10.0 (241 Reviews)
Cabin
On the Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • TV

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Betty's Vineyard House - On the Shawnee Wine Trail - Walk to/from the Winery! From US $194
         

10.0 (94 Reviews)
House
Betty's Vineyard House - On the Shawnee Wine Trail - Walk to/from the Winery!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful location in the secluded woodsn From US $178
         

10.0 (68 Reviews)
House
Beautiful location in the secluded woodsn
  • Air Conditioner
  • Parking
  • Pet Friendly

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Wine/Bourbon Trail Carriage House, Cozy, Clean, Hiking, Shawnee Nat'l Forest, From US $249
         

10.0 (43 Reviews)
Cottage
Wine/Bourbon Trail Carriage House, Cozy, Clean, Hiking, Shawnee Nat'l Forest,
  • Air Conditioner
  • Parking
  • TV

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Hilltop Retreat, a modernly-rustic getaway! From US $282
         

10.0 (40 Reviews)
House
Hilltop Retreat, a modernly-rustic getaway!
  • Air Conditioner
  • Parking
  • TV

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Historic Home, Modern & Charming Decor, Wine Trail, Private Rental From US $311
         

10.0 (38 Reviews)
House
Historic Home, Modern & Charming Decor, Wine Trail, Private Rental
  • Air Conditioner
  • Parking
  • TV

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On the Lake & Wine Trail & a Perfect Getaway for 16+ With an ADA Suite! From US $860
         

10.0 (16 Reviews)
House
On the Lake & Wine Trail & a Perfect Getaway for 16+ With an ADA Suite!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Havisham Bourbon Bar - Suite 18 - private, spacious, wine trail apartment From US $252
         

10.0 (14 Reviews)
Apartment
Havisham Bourbon Bar - Suite 18 - private, spacious, wine trail apartment
  • Air Conditioner
  • Parking
  • TV

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Cozy 2-BR cabin with bonus loft bedroom by the Wine Trail in the Shawnee Forest! From US $190
         

10.0 (11 Reviews)
Cabin
Cozy 2-BR cabin with bonus loft bedroom by the Wine Trail in the Shawnee Forest!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub Cabin- In the Heart of Shawnee Wine Trail From US $308
         

10.0 (4 Reviews)
Cabin
Hot Tub Cabin- In the Heart of Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub Cabin- In the Heart of Shawnee Wine Trail From US $241
         

10.0 (4 Reviews)
Cabin
Hot Tub Cabin- In the Heart of Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • TV

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Hot Tub Cabin- In the Heart of Shawnee Wine Trail From US $300
         

10.0 (3 Reviews)
Cabin
Hot Tub Cabin- In the Heart of Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub Cabin- In the Heart of Shawnee Wine Trail From US $298
         

10.0 (3 Reviews)
Cabin
Hot Tub Cabin- In the Heart of Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub Cabin- In the Heart of Shawnee Wine Trail From US $241
         

10.0 (1 Review)
Cabin
Hot Tub Cabin- In the Heart of Shawnee Wine Trail
  • Air Conditioner
  • Parking
  • TV

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The Bitty House One, next to a winery! From US $173
         

9.8 (53 Reviews)
House
The Bitty House One, next to a winery!
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pomona Winery.

Weather in Pomona Winery

View the weather forecast for Pomona Winery before booking your Pomona Winery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pomona Winery, IL

Sailings offers a large selection of top attractions around Pomona Winery. Research things to do on your vacation before you visit Pomona Winery.


Southern Illinois University Shawnee National Forest Isle Casino Cape Girardeau Southeast Missouri State University Lake of Egypt Giant City State Park Hunter Valley Winery John A. Logan College Railroaders Memorial DuQuoin State Fairgrounds SIH Medical Group Trail of Tears State Park Marion Cultural and Civic Center National Shrine of Our Lady of the Miraculous Medal Elzie C. Segar Memorial Park Vienna City Park Ferne Clyffe State Park Crab Orchard National Wildlife Refuge Eden Spa & Salon Marion Carnegie Library

Pomona Winery Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Pomona Winery?

Currently, the total number of properties listed in 2026 is over 66 in the Pomona Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pomona Winery.