All Inclusive Vacations from Winnipeg

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  Ocean El Faro-el Beso Adults Only

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • El Beso Junior Suite Pool View
  • Dec 03, 2026 (7 days)

  was $18459 Save 91%

  $1699 PP incl. taxes & fees

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  Be Live Collection Marien

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Puerto Plata, Dominican Republic

  • All Inclusive

  • Superior Deluxe Pool View Queen
  • Dec 29, 2026 (7 days)

  Book with Deposit

  was $4555 Save 56%

  $2012 PP incl. taxes & fees

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  Breathless Punta Cana Resort and Spa

  • Hotel rating 5.0 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Allure Junior Suite Pool View King
  • Dec 31, 2026 (7 days)

  Book with Deposit

  was $5499 Save 49%

  $2809 PP incl. taxes & fees

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  Grand Palladium Punta Cana

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Junior Suite Poolside
  • Nov 04, 2026 (7 days)

  was $3265 Save 45%

  $1786 PP incl. taxes & fees

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  Ocean El Faro

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Junior Suite Nature View
  • Nov 13, 2026 (14 days)

  was $4869 Save 41%

  $2897 PP incl. taxes & fees

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  Sunscape Coco Punta Cana

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Deluxe Tropical View King
  • Mar 18, 2027 (7 days)

  Book with Deposit

  was $3159 Save 40%

  $1899 PP incl. taxes & fees

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  Secrets Tides Punta Cana

  • Hotel rating 5.0 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Junior Suite Gardenview King
  • Feb 17, 2027 (7 days)

  Book with Deposit

  was $5459 Save 40%

  $3278 PP incl. taxes & fees

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  Catalonia Bavaro Beach Golf and Casino

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • All Inclusive

  • Privileged Deluxe Junior Suite
  • Nov 04, 2026 (7 days)

  was $2985 Save 39%

  $1835 PP incl. taxes & fees

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  Hodelpa Caribe Colonial

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Santo Domingo, Dominican Republic

  • Only Breakfast

  • Room
  • Dec 20, 2026 (7 days)

  Book with Deposit

  was $3035 Save 39%

  $1865 PP incl. taxes & fees

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  HM Bavaro Beach

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Punta Cana, Dominican Republic

  • Only Breakfast

  • Pool View Room
  • Dec 09, 2026 (7 days)

  Book with Deposit

  was $2705 Save 39%

  $1658 PP incl. taxes & fees

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  Royalton Negril Resort and Spa

  • Hotel rating 5.0 out of 5 stars
  • Winnipeg to Negril, Jamaica

  • All Inclusive

  • Diamond Club Luxury Junior Suite Swim Out
  • Dec 13, 2026 (14 days)

  Book with Deposit

  was $13689 Save 51%

  $6739 PP incl. taxes & fees

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  Hideaway at Royalton Negril

  • Hotel rating 5.0 out of 5 stars
  • Winnipeg to Negril, Jamaica

  • All Inclusive

  • Luxury Junior Suite Oceanview
  • Dec 06, 2026 (7 days)

  Book with Deposit

  was $4899 Save 45%

  $2709 PP incl. taxes & fees

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  The Verandah Resort and Spa

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Waterview Suite King
  • Jan 13, 2027 (7 days)

  Book with Deposit

  was $7457 Save 50%

  $3711 PP incl. taxes & fees

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  Hammock Cove Resort and Spa

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Signature Villa
  • Dec 02, 2026 (7 days)

  was $13851 Save 39%

  $8432 PP incl. taxes & fees

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  Margaritaville Island Rsv Cap Cana Wave

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Aruba, Aruba

  • All Inclusive

  • Junior Suite Poolside Terrace King
  • Dec 02, 2026 (7 days)

  was $6622 Save 37%

  $4170 PP incl. taxes & fees

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  St James Club and Villas

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Club Room
  • Oct 25, 2026 (7 days)

  was $4565 Save 35%

  $2982 PP incl. taxes & fees

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  Starfish Jolly Beach Resort

  • Hotel rating 3.0 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Room Double
  • Oct 25, 2026 (7 days)

  was $3855 Save 35%

  $2512 PP incl. taxes & fees

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  Pineapple Beach Club

  • Hotel rating 4.0 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Room Gardenview
  • Oct 25, 2026 (7 days)

  was $4535 Save 30%

  $3152 PP incl. taxes & fees

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  Galley Bay Resort and Spa

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Gauguin Suites
  • Dec 02, 2026 (7 days)

  was $8629 Save 29%

  $6122 PP incl. taxes & fees

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  Royalton Antigua Resort and Spa

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Diamond Club Luxury Junior Suite Bay View
  • Dec 02, 2026 (7 days)

  was $4729 Save 28%

  $3392 PP incl. taxes & fees

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  Sandals Grande Antigua Resort and Spa

  • Hotel rating 4.5 out of 5 stars
  • Winnipeg to Antigua, Antigua and Barbuda

  • All Inclusive

  • Mediterranean Club Level Suite
  • Oct 25, 2026 (7 days)

  was $6505 Save 26%

  $4842 PP incl. taxes & fees

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  Hyatt Regency Aruba

  • Hotel rating 5.0 out of 5 stars
  • Winnipeg to Aruba, Aruba

  • No Meals/Drinks

  • Dec 12, 2026 (7 days)

  Book with Deposit

  was $5555 Save 26%

  $4111 PP incl. taxes & fees

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